Finding Love Again After Loss

How do you navigate love after loss?  

Emily sits down with Jennifer Osler-Bolton and her husband Michael Bolton, a couple that found love after Jen’s devastating loss of her firefighter husband, Ryan.

Their candid conversation explores the unique challenges of dating a widow, blending families, and how to honor a late spouse while embracing a new love.  

Through humor, wisdom, and raw vulnerability, they reveal the delicate balance of moving forward while cherishing the past, and how Michael’s love for Jen extends to protecting Ryan’s memory.  

This is a powerful exploration of grief, love, and resilience. 

Listen For:
5:48 – The reality of love after loss
17:22 – Family concerns about dating a widow
34:29 – “Two separate husbands, not a competition”
46:09 – The reality of dating a widow: Compassion and patience 

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Guest: Michael Bolton and Jennifer Osler-Bolton
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Transcript

Emily Cave (00:00:02):

When I was thinking about recording this episode today, it reminded me of a line that I wrote in my book, and I said, I kind of didn't know what I wanted to say, and I can't believe that this is my first episode, or that this is the first line in my book. And when I look back on my journey in the past four and a half years, one of the things that has shocked me the most during my grief and I feel has really defined me, and I have really tried to remind myself that I am so much more than that was people's judgments and people's opinions on me moving forward with my life, not on but forward. So this episode is for young widows or older widows who are considering dating again or who have remarried again, or maybe you're a friend of a widow or a family member of someone who is dating or married to a widow.

(00:00:58):

This episode is for you guys. This special guest that I have on are some of the closest friends that I've made during my widow journey, Jen and Michael. Jennifer has become one of my go-to girls. She became a widow at 36 years old to her firefighter husband Ryan, who was killed in the line of duty. After his death, she was convinced that she would never love again and also never date a firefighter again. But three years later, she literally crossed paths with an Irish firefighter named Michael, who now also works at the same fire hall that Ryan works at. And they are coming up on celebrating their fifth year wedding anniversary. And I could have not thought of a better couple to have this heartfelt but difficult conversation with because they are just such an inspiration and a role model to how this all should be done. And I know that there's no textbook, but their relationship is very special and one that I admire so much. Hi friends.

Michael Bolton (00:02:22):

Hi. Got Mike.

Emily Cave (00:02:23):

How's it going? It's good. It's good.

 Jennifer Osler-Bolton (00:02:26):

I want to go get my hat now. Should I go get my hat?

Emily Cave (00:02:28):

Yeah, you should definitely go get your hat

 Jennifer Osler-Bolton (00:02:30):

Reveal. Where is it? You in my closet. I'm going to go grab it. Perfect. Hold that. I'll back. Look

Emily Cave (00:02:34):

Here. I want to match.

Michael Bolton (00:02:37):

Well, you thank you for the hot. It's cool. I like it.

Emily Cave (00:02:39):

Oh my gosh. Thanks for doing this. I know it's your day off,

Michael Bolton (00:02:43):

So Yeah, no worries. All it's good. Hopefully we can help some people.

Emily Cave (00:02:48):

Yeah,

Michael Bolton (00:02:48):

Serious. That's main goal, isn't it?

 Jennifer Osler-Bolton (00:02:51):

Now feel these are really nice hats, Emily. Really nice. You did a really good job. I feel

Emily Cave (00:02:58):

They, yeah, I am sending them to the special guests. I feel like it's a good tie in. I love it. Okay, so Michael, what was your first reaction to Jen being a widow?

Michael Bolton (00:03:18):

Yeah. Well, we talked about this earlier and just obviously when you meet someone new, a lot of things are in the air. And I guess initially, if I'm being totally honest, it didn't really register when Jane told me she was a widow. I obviously acknowledged that she had been through a loss. But then over time, as we talked, and I got to see the depths of that, the depths of the impact that that has been. But first of all, we were trying to deal with the first moments, the following love part. But yeah, I grew to become familiar with exactly what had happened to Ryan and the impact that it had on not just Jen, but the kids. And for me, as time went on, I guess I came to realize it was a bigger thing than I first realized in a good way, just as I learned about Ryan's accident and about his legacy, as I met more people who knew him.

(00:04:36):

The reality is Ryan was and still is part of his family, and it's something I came to accept. I came to accept. For me, it hasn't been a big hindrance for me. As I said there, Ryan died doing his job. He died as a firefighter, which I could identify with. He died honored his country, and therefore he died a hero. And that's something that I very quickly embraced. People have asked me about this, and I do say to them, I wasn't a result of Ryan's death. So the something that I feel I could openly honor, and obviously as I grew more to love Jen and the kids, then it became part of who we are. So I think ultimately, if that love wasn't there between us, then things could probably be a bit different. But ultimately, I love Jen and

Emily Cave (00:05:48):

I love her too. Yeah,

Michael Bolton (00:05:49):

I needed far easier to accept.

Emily Cave (00:05:52):

I said, I love her too. So you would say that in the beginning, I feel like you kind of nailed it, to be honest. In the beginning, you hear the word widow, and I feel like that's just grief in general. You can't grasp it until you're more in it and you realize how impactful it is. And that grief never goes away where I feel like, yeah, when people hear the word widow, it's kind of brush, I don't know if brush off is the appropriate term, but it's like, oh, Jen has brown hair. It's a part of her, but you don't realize how much it is a part of her until you're deep in it with her more.

Michael Bolton (00:06:38):

I totally agree.

 Jennifer Osler-Bolton (00:06:40):

Yeah. There's a lot of facets of widowhood that nobody knows until you're walking through it with the widow until, like you said, that was actually really good. Oh yeah, Jen has brown hair. Oh yeah, she's a widow. And people seem to brush that off or just like, oh yeah, that happened to her and it's so awful. But oh, well, look, she's remarried. She's so happy now. And it's like Michael actually has the firsthand experience of what it is to live with a widow, because the only other people who would know would be the widow herself, and if she has kids, but then she's trying to raise her kids through that trauma. And so for Michael to come in, I could see where it might sound like, oh gosh, that's so daunting. But when it stems from literally like, well, I saw this girl and I wanted to know more about her, I found out she was a widow. And so because I fell in love with her, I want to know more about that. Tell me about that. So I think it's something that, it's a very unique situation that a lot of people on the outside don't have a firsthand experience with until you're with the widow.

Emily Cave (00:07:44):

Do you guys want to say the summary of how you guys met? Yeah, sure.

Michael Bolton (00:07:49):

Yeah. I mean, there's obviously two different stories.

Emily Cave (00:07:54):

Yeah, I want to hear, hear the girl version and the

Michael Bolton (00:07:58):

Guy version. Super interesting. So for me, you should actually that you go first because you're way more interested than me. So me, I basically, firefighters for Christ is the organization, which was held the annual retreat up in Hume Lake. And for me, it's something I always wanted to go to, but the door had never really opened. And 2019, a good friend of mine, we got together and he said, Hey, or one of us, do you want to go over the Hume Lake for the retreat? So we made a whole trip off it. We flew into California, we went down to Universal Studios, we walked up to the LA side, or sorry, yeah, the LA side, sorry, the Hollywood sign and did all the things. But obviously when I ended up to shame, I had no intention at all of being there to meet someone. It used to be a couple's retreat, but it then became just an annual retreat. So yeah, so I remember being, it was like a Thursday morning, is that right? A Friday morning? It was one in the morning, one of the first mornings. I remember walking into the church and it was a little bit late. It was hard to believe J was actually early. Wow. You know what I mean?

(00:09:15):

As I walked into the church and sat there and I looked over and I was like, whoa, who's that? It was sort of like a first sight thing.

Emily Cave (00:09:26):

Love it. First

Michael Bolton (00:09:26):

Sight. Oh yeah, for sure. I give my friend a nudge. I was like, Hey, check her out. Good. And then, yeah, I was super curious as to who she was. Obviously I thought she did the fire painter, which she laughs at. But the other thing is, shortly after that, it was breakfast time and we walked over toward the dining room, and as we were walking over, James was our cousin, and we sort of crossed paths and I tried to talk to her, but she was very shy

Emily Cave (00:10:03):

In your accent.

Michael Bolton (00:10:04):

Oh, in my accent, yeah. But she was very, very shy. She didn't want to talk to me. Long story short, over this series of the three days, I tried to talk to her four times with, yeah, no, she

 Jennifer Osler-Bolton (00:10:17):

complete rejection.

Michael Bolton (00:10:18):

Yeah. She's just like, and then she said to me, when you left, you didn't say goodbye. I was like, guess because she wouldn't, you wouldn't talk to me. No wonder I said goodbye. So yeah, so then I left and I got home and well, Jen's big on Instagram, her Instagram, and then I was at home sitting on the couch watching tv, and I get a Instagram text on my phone, and of course it's Jen. Hi, it's Jen here from Human. I was like, seriously, what is going on here?

Emily Cave (00:10:47):

You're like, where were you during the retreat when you were avoiding me? Now I'm halfway across the country. Exactly.

Michael Bolton (00:10:54):

That's exactly right. And we actually didn't get to see Joe again until June, but the retreat was in March, but that was really it. From there, it just flourished. And here we are, five years old, married. So yeah, gr

Emily Cave (00:11:10):

Way to go. Okay, John, let's hear your version.

 Jennifer Osler-Bolton (00:11:13):

Well, obviously the perspective of it is similar. He described it perfectly. It was very accurate. He tried talking to me and I completely ignored him. And I think because I was not like Michael, we weren't going to this retreat to, oh, I hope I meet somebody. I was actually going because I was hired to be there to be a speaker. So I was there on a job. I was there to work, and I was very convinced I didn't want to be, if I was going to be with somebody again, I didn't want to be with a firefighter. I didn't want to be. I was kind of done with the fire life. I was so convinced that, nope, it's not another firefighter. I don't want to be with another firefighter. So my eyes were truly closed. I was like, Nope, absolutely not. I'm here to do the Lord's work.

(00:12:01):

That was it. Yeah. So truly as we were walking, Michael said, we crossed paths, but before we actually encountered each other, I felt super nervous and I felt like, oh gosh, I don't get panic attacks. I don't get nervous before I speak. That doesn't happen. But I really felt like there was something inside of me that felt nervous. I was like, I need to go sit down. I need to get a drink of water or something. And then when we crossed paths, I truly intersected and all of a sudden he's standing there and I looked up at him and I just, everything amplified a million times in my body. And I was just like, oh my gosh. In the two and a half years since Ryan had died, I never found another man attractive. I was just like, the idea of dating made me feel sick to my stomach, but looking at this man, I'm like, oh my gosh, he's so attractive. I couldn't remember his name when he said, I was just like, thank God. It's

Emily Cave (00:12:57):

The accent.

 Jennifer Osler-Bolton (00:12:58):

It was the accent.

(00:13:00):

Thank God. He had, you know how when you go somewhere, a retreat, you have the lanyard with the name badges? I was like, okay, good. Thank God he had that on because I couldn't, I heard nothing. It was just, yeah, he's trying to talk to me. It wasn't happening. And so then I left the area after a little bit, and so up at that retreat area, there's no cell service, so you have to buy the wifi there. So that's what he was trying to help me do, and I was like, Nope, nope, thanks. I'm good. I got it. Don't worry about it. I don't need your help. It was so like, no, no, no, I'm okay. Thank you. Finally got connected, and then I walked away from the area. I was so overwhelmed by it. And so all these text messages started coming through because I hadn't had any service up to that minute. And so a text came through and the joke was was that I was going to go to this retreat and I was going to meet my future husband, and I was like, not a chance. I didn't want a firefighter, not a chance. So I get this text message and it says, so have you met your husband yet? And I sent back a text and I said, he's from Ireland. I did.

Michael Bolton (00:14:03):

She never told me no.

Emily Cave (00:14:06):

Do we have that text message? Do you have a, I love that you still have it. You should frame that.

 Jennifer Osler-Bolton (00:14:11):

I know

Michael Bolton (00:14:11):

It's true.

 Jennifer Osler-Bolton (00:14:13):

It was bizarre. But there was something that I knew. I just knew that there was something, and I don't know that I necessarily believed in love at first sight, but there was definitely something that had happened because we found out, after we were married, we found out that we were the only two single people that were registered for the retreat. As Michael said, it was previously known as a couple's retreat. We were the only two single people registered to be there. And the way that my, I always, I say my spirit, my soul kind of locked in on him. He describes it as the same thing, meaning he walked into the sanctuary wherever we were, and it was, for whatever reason, just zoned in on me. It was just this instant for both of us. Well, who's that? What's going on there? And so it's super, I believe divinely orchestrated for us to be there. And Ryan is actually connected to that place too, because a year before he died, that camp was surrounded by fire, and Ryan was on that fire at that camp. So he was there working to protect that camp where years later I would meet my future husband.

Emily Cave (00:15:21):

Did you know about Ryan when you ran into her, Michael?

Michael Bolton (00:15:26):

No, I didn't know. No, not at all. It's just when we spoke, she even said that. She mentioned she was a widow, but I didn't, again, it wasn't something that was in my,

Emily Cave (00:15:36):

It's like stay away

Michael Bolton (00:15:37):

And say No. That's right. She said, she mentioned she was a widow, but I didn't even pick up on that. Again, you know yourself when there's a new relationship, or sorry, I knew attraction. You're not really, it's strange actually, just to acknowledge that whenever

Emily Cave (00:15:52):

It's like, okay, she has brown hair, she's a widow.

Michael Bolton (00:15:55):

Just whenever you meet someone and they

Emily Cave (00:15:57):

Start, her name's Jen.

Michael Bolton (00:15:58):

Exactly. I knew her name is Jen. But whenever you meet someone and they maybe give you some really important information at the start, and you're like, yeah, okay, whatever. You know what I mean? You're like, whatever. But that, I think that's something we all do. We listen and we take in what the person said, but then we are obviously trying to pursue whatever that attraction is or whatever that connection is. And it's not until later on that we actually realize what they said in that moment or start to realize the magnitude of who they are or, so yeah, that's definitely something that we talked about on our walk, and it is something to acknowledge that we do that as humans. So we say, Jen said she's a widow, and I'm like, all right, okay. She had a loss. But then we get to see the food magnitude of that as time plays out.

Emily Cave (00:16:51):

That makes sense. Okay. This one is a sensitive one, Michael. Did you have any friends or family that had reservations or concerns that Jen was a widow and how that would impact you? Or they were worried about her still being in love with Ryan and you not getting her full love, if that makes sense?

Michael Bolton (00:17:22):

Yeah,

Emily Cave (00:17:24):

People's opinions. And did that impact you? Did that make you anxious? Did you take them to the heart? How did you learn how to filter them, et cetera?

Michael Bolton (00:17:33):

I would say that I didn't have that obstacle in my life when I started speaking to people. Well, the biggest obstacle goal, because our relationship is very unique in regards of two different countries, 6,000 miles apart, the people were more concerned about the destination than the widow part. So people were asking, what are you going to do? Are you going to move? Is Jane going to move here? But what I see in that moment is that people don't actually see the relationship. They don't see that we're falling in love with each other. They don't grasp that. So again, when I told people Jim was a widow, obviously Ryan was a firefighter. I came from a previous fire department. People were astonishing sister taken back by the accident and how the accident happened and how Ryan was killed. But I think you can tell people a lot of things, but they don't really grasp it until they actually meet the other person. So for me, whenever, if people did have any doubts, which they never expressed to me about Jen being a widow, I think when people started to meet Jen and they realized how special she was and what we had, and I think for me, people were just happy to see me happy. My close friends and family again, it might've been overshadowed by the widow aspect, might've been overshadowed just by the difference in where we lived and how that was going to work out.

(00:19:07):

So I would say for me, no, but it wasn't an issue for people. Did you ever hear me talk about what, no. If it was ever an issue for four people, yes.

Emily Cave (00:19:21):

Would you see it the same? Jen, would you say that you had people concerned, or when they met Michael, they felt better?

 Jennifer Osler-Bolton (00:19:30):

Well, I think being on the widow side of things, naturally, my parents were very like, is this man going to take care of you? Because they watched me go through so much. I mean, my dad, my gosh, my dad, I was just telling Michael a story the other day about, because I was working at the time and I don't know, maybe a year later, and my dad's babysitting my kids for me, and I get home from work late and he says, hi, I made you dinner, but I forgot to bring it over. Let me go get the dinner. They live like a mile away. And I was like, okay. So I don't know. He was, so I got to bring you this plate of food. And I was like, okay, dad. And so he brings it over, and I was telling Michael, it was like a bowl of macaroni and cheese with kind of hot dog in it.

(00:20:11):

It was the sweetest thing. But I was just like, but his care for me, he was just like, I can't even let you go a day without a meal. So my parents were very much, I mean, I'm their daughter. They watched me go through such heartache. And so their concern was definitely more on the lines of like, is this a good man? Is he going to come in and take care of you? But then also because Ryan was their son as well, Ryan and I had been together for 22 years. So they watched Ryan grow up from the time he was 16 years old. And my dad especially still to this day, get emotional talking about Ryan. And so I think it was important not just is this man going to come in and take care of our daughter, but is this man also going to come in and take care of Ryan's memory because it's attached to their grandchildren?

(00:21:00):

It's attached to their daughter, plus their own memories that they have with Ryan. My parents did trust me with that. I mean, truly, they really did put a lot of trust in me in what I was sharing about Michael and how I felt about Michael. But even on the side where Michael's talking about the people in our lives, distance was the primary concern just because, again, our situation's unique. But I have noticed that with his family, his family has really, really done a good job to embrace Ryan. He has a cousin who lives here in California, and if I post something on Instagram or whatever, she's really sweet to just meet me at that. And I'm sure today's a hard day for you or whatever it might be. And his family has really embraced not only me and my kids, but without ever knowing Ryan, without ever meeting Ryan, without ever understanding even what that was like when we went through it. They've embraced all of that with me. It's just a part of me where I go, Ryan goes. And so Michael's friends and family have been really welcoming. I mean, truly, I think every single person in his life that now it's been five years, but I felt very, very welcomed by everybody in his life. Nobody made me feel

Emily Cave (00:22:24):

Weird. I feel like it's so important to acknowledge that part

(00:22:31):

Because there was a whole you before Michael, and that should never have to be erased. You talking about your dad though, totally reminds me of my parents. I know you met my parents, obviously, but yeah, just they lost. They watched their daughter go through something so horrific. And then they also, like you said, lost a son too. And I feel like, I don't know about your parents, but my parents, especially my dad, I feel like my dad being the one trying to figure out the business side, cook meals, all of that, he didn't really get time to grieve right away. He was being a dad. And yeah, big. I have a soft spot for my parents for sure, but I could have a million episodes about how much they don't get enough credit hard For them.

(00:23:33):

That's hard. Yeah, it's very hard. And that needs to be acknowledged as well. I think when someone marries or is dating a widow, their family and friend grief need to be acknowledged too. You're kind of dating everyone's or marrying into That's true. The family, right? It wasn't a breakup, it wasn't a divorce, it wasn't anything like that. They were very much still alive and in it when they passed away. Speaking of grief days, Michael, what do you do? I mean, I've seen on social media, and this is why I wanted you guys on, because I know no relationship is perfect by any means, but Michael, I feel like you, Jen, being a widow sister and you love her so well and show up for her and show up for Ryan. And I remember even on one of my grief days, you messaged on the wedding, you messaged and then talking with the Edmonton Oilers in the Stanley Cup, you sent a picture from the fire hall and watching the game. And just for you to even have that open mind to acknowledge that type of stuff, that would be so hard. I know means a lot to me. And I know obviously means a lot to Jen and the kids, but in the beginning, was there, I don't want to say jealousy, but were you worried to step over toes or what did you want to do on grief days? Or what would you recommend or what do you think works for you guys?

Michael Bolton (00:25:21):

Yeah, I mean, obviously grief days are special days in the year, but I would like to start by saying that every day in this house is that Ryan is honored almost every day. He's talked about almost every day. And that's part of who we are. That's part of, I love Jen so much that, and as her husband, I feel it's my role to give her that space and that support to do that. And ultimately what happened to Ryan was nothing directly to do with me. You know what I mean? So I came in afterwards and who am I to come in and say, Hey, you can't talk about Ryan, or you can't honor him. I mean, Ryan has a memorial in our house. His pictures at the front door. He is part, he's just part of who we are as a family. And again, as a fellow firefighter, I totally respect of his service to the country. And obviously he had that horrific accident, which cost him his life. But so for those days, I guess I'd just be respectful. You know what I mean? I'm always respectful of who he is. Sorry, on those days or days where I actually get the privilege of joining in, I get to hear stories about Ryan, you get his favorite food, you do stuff to celebrate him. His birthday,

Emily Cave (00:26:52):

What's his favorite food?

Michael Bolton (00:26:53):

So his favorite food is the totally opposite to what I like. It's disgusting. It was Taco Bell. He loved Taco Bell.

Emily Cave (00:27:01):

Oh my goodness. I had Taco Bell for the first time a while ago. I'm team Michael on that. I feel like I can't stomach it, but I would do it for Ryan.

Michael Bolton (00:27:11):

Yeah,

Emily Cave (00:27:12):

That's exactly what he does.

Michael Bolton (00:27:13):

Yeah. But I am super grateful that I can be part of that. And someone asked me recently, they said, Hey, I got chatting to them, and they've never asked me about, it's actually people who knew Jen and who knew Ryan. And when I was with this guy, he sort of said to me, well, hi, is that, is it awkward? You know what I mean? He basically said to me, I don't know how you do that. I dunno how.

(00:27:42):

And I'm like, well, what's a big deal? You know what I mean? What is a big deal? Ryan lived here. He was killed tragically. And the family a forever to grieve at. You know what I mean? It's always going to be there. I know it's something that's never going to go away. I have no desire for it to go away. It doesn't bother me. And so those days, I say, I am the one who has, who's privilege to be able to join in and hear more about Ryan and to be there with the kids. And ultimately, we talked about it earlier. That all just comes down to how much I love Jen. I love Jen. I love the kids are my own. You know what I mean? And I want to be there. I want to be there to support them and celebrate with them. So that's why I stand out.

Emily Cave (00:28:36):

Jen, what is something that Michael does, whether that's tidying up his grape site or flowers or something that you really appreciate and would encourage someone else to do? Oh my gosh, look, I'm getting

 Jennifer Osler-Bolton (00:28:53):

Big teary. I wasn't expecting that. You didn't send me that question

(00:29:00):

Feeding much. I'm not prepared. So there was a really, really poignant part at the very start of our relationship before we talked about marriage, before we talked about anything that I was like, this is the man I'm supposed to be with. And so the night that Ryan left for the fire, my daughter ended up taking a picture of me and Ryan as we were hugging, literally as he was leaving to not come home. So it's our very last moment together. My daughter captured it. So naturally after Ryan died, I took that picture and I framed it and it's on my bedside table and it's there. So I remember my phone, I meet and we would FaceTime, have our dates on FaceTime. And I remember telling him that I had about this picture, I had this picture and it's on my nightstand. And Michael had said to me, he said, just so you know, that picture never comes down. I don't ever take that picture down. And I remember in that moment thinking like, okay, is this guy too good to be true? Okay, sure. You're like every widow's

Emily Cave (00:30:09):

Dream to hear from someone that they're dating or

 Jennifer Osler-Bolton (00:30:13):

Right, totally. So it's like, I loved it, but then I was like, okay, but is it real? And five years later, that picture is still on my bedside table. And so every night Michael goes to bed with me and that picture is still there. And I know that that's an extreme case of wow, that's an incredibly selfless heart and selfless love. But the bottom line of that, being able to love in that way is because Michael loves me and who I am and what I've gone through, that's a part of me that he loves as well. He knows that who I am today as a result of what I've gone through. So you couldn't love who I am today and then say, okay, but get rid of your past because that past made me what he gets now, this version of me that he gets now and his ability to love me with my past, which is what allows him to do things like that, drive out to the cemetery with me and literally clean up Ryan's headstone for me.

(00:31:18):

Or we had something not long ago where he came across something of Ryan's from work and he was just like, text me. You're never going to believe what I found and brought it home so that I could see it and I can have it. And just things like that. He's always looking out for Ryan's memory, but it's for me, it's not in an effort to look good or be good or look at what a good husband I am. I do this so well. It's a genuine, Jen's got to see this. I got to bring this home for her. So he loves that part of me. And I don't think if that love wasn't there, he wouldn't be able to do those things. If it was a surfacey kind of love, there might feel like there's this competition. And he doesn't do that because it's genuine.

(00:32:05):

It's a genuine, authentic love for me as a person. And what this past is, we all have a past. We all have things we've been through. We all have things that we're going to come in with. And especially when we met, we were tipping on 40 years old, so we're both coming in with past and history and all that kind of stuff. And it would be like me saying, well, Michael, I think you're great, but I can't accept your past, so this isn't going to work, and I'm not going to accept your past. I wouldn't do that to him. But for some reason with widowhood, people think it's one or none. You either stay loyal to the one that came. It's the truth. People either want you to stay loyal to the one that's died, and so you then have to live in loneliness forever, or they want you to let go of that one because you need to only live for your present. And it's difficult with widowhood because like you said, it's not, it wasn't by choice. It's not divorce, it's not a breakup, it's not anything like that. It was something that interrupted the plans we had for our future. And so I think that when someone can come in and love the widow and love the person for who they are now, they naturally have to find a way to love the past that made that woman who she is today.

Michael Bolton (00:33:21):

And also come in with the understanding that I think something that could have led the disaster, which I do know it's probably a preconception of people that I could possibly come in and try and to replace who I was. I'm pretty sure people have thought that not just maybe with every widow, you know what I mean? You're going to come in and try to replace the guy who was there, but it's definitely not that Ryan was who he was, and he loves Jim as he did, and I am who I am. I'm not trying to be Ryan. Do you know what I mean? And thankfully, I've been given space by Jen and the kids to be who I am. You know what I mean? And that's how we connected because of who I am, not because Jen's trying to find someone who's like Ryan's. You know what I mean? It's certainly not so, and I think that's made easier for me because as I said earlier, Ryan is who he is, and I am who I am. And it's two separate, obviously, Jan has had two husbands, but we're separate husbands. You know what I mean? So it's not a competition and it makes it easier for me to honor him, if that makes

 Jennifer Osler-Bolton (00:34:29):

Sense. Actually, if you don't mind, I'm sorry, but that's actually something when you were talking, I think that that does make it easier for him to be willing to be so open and gracious to Ryan's memory is because I don't put that comparison on him. I don't expect him to come in and do things the way that Ryan did, or they are two very different people. They are similar in a lot of ways, but they're very different. And so that is something that I think is widows too. We have to be careful of when going into a relationship with someone because yes, we want our late husbands to be honored. So well, I don't think it's unfair to say we have an expectation for them to be remembered well, but we do also have to grant that ability to, the ones coming in, if Michael were to come in and I were to make him feel like he's in competition with Ryan, I don't think he would be able then to honor Ryan the way that he did.

(00:35:28):

It would just build a natural resentment towards me, towards Ryan, whatever. But that is something, as a widow is hard to do. It's hard to find that boundary and that balance of I love and honor my late husband, and I will forever. That's just a piece of who I am. But at the same time, I need to come in and elevate Michael to my number one spot to not as a replacement, but just as a, you're here living this life with me. I want to elevate you and respect you and honor you for the person that you are. And I think that when we do that as widows, that does then allow them the freedom to explore honoring our late husbands the way that we hope that they would. Would you agree with that?

Emily Cave (00:36:15):

I feel like widows, obviously you on Instagram and all that, being in the public eye too, something that I feel like I'm always even, I feel I've definitely gotten better at it, but in the beginning when I started dating Colin, it's like you post one photo of Colin, okay, you got to post one photo of Colby, or you got to post. It's trying to balance it because you get judged either way. If you're posting about Colby or talking too much about Colby, or you're talking too much about Ryan, then it's like, poor Michael, Michael deserves better, et cetera. But then if you're posting about Michael, then it's like, Ryan deserves better. You've moved on. So I feel like, as you said, balancing that as a widow and then also not projecting that into the relationship too is very important. But one thing that I liked when Michael was talking, and it just sounded the way that you were speaking about it, is not only are you protective over Jen and the kids, but the way that you talk, you're also protective over Ryan and his legacy and the way how that is grieved and treated.

(00:37:28):

And I just think that's so beautiful and so kind, because it isn't always necessarily that way. So when you were talking, I could feel like it's like, no, when you're talking about finding things that the fire hall and all of that, you are protective of that because that is a huge part of Jen and the kids, and she deserves to see those things or would want to see those things. And I think that's really cool. Okay, both of you, any advice on dating a widow down to Jen? You can talk about when to take off rings or not take off rings or memorials, et cetera, or what you do with gifts. Michael, from you coming in, what would you want to say? Do

Michael Bolton (00:38:18):

You want to talk about the rings? I know what was,

 Jennifer Osler-Bolton (00:38:21):

Yeah. Well, I still have a ring that Ryan gave me that I wear. He gave me that for our 10 year anniversary that I still hold onto. But I wore my wedding rings for two and a half years after Ryan died. I tried a couple times and I was like, it just felt in my heart, I just wasn't ready.

(00:38:42):

I still felt married. I still felt, even though I knew in my heart I wanted to be loved, I definitely wanted to be loved again. I was 36 when Ryan died, so I was hoping I wouldn't be alone forever, but I wasn't ready yet. And then oddly enough, as part of our story goes, I felt a nudge on the two and a half year mark to take off my ring. And so I was like, well, I'll take it off and I'll try it. And so I took it off and it didn't feel uncomfortable. It felt right at that time, and it exactly a week later is when I met Michael. And so I always think about that. If I had been wearing my wedding ring, he wouldn't have talked to me, wouldn't have. So I am grateful for that. But when it comes to things like that, or even still, because obviously we're in the house that Ryan and I bought together, so there's a lot in here that was touched by Ryan, literally in regards to fixing things or not fixing things.

(00:39:40):

And so one of the most difficult things for me as a widow was trying to allow this home to feel like Michael's home. Not because it didn't feel like that for me, but I wanted so badly for him to feel comfortable here in this home and turn this into his home rather than, well, this is Ryan's home and so can I do this? Can I do that? I never wanted him to feel that way. I wanted him to feel open and welcome to that. And so this is where I am grateful for the distance that was between us for a long time, because it allowed me to slowly go through things in the house and slowly move Michael into the house without this rush of, okay, hurry up. We're married, everybody, let's go to the next step. And I think that sometimes that's normal, right?

(00:40:29):

People get married and it's like, oh, we moved into the house together, or we did whatever together. But with widowhood, it has a totally different attachment to it. And so my advice to any widow when they're entering into the dating scene or anything like that is just slow. Go slow. Not for the sake of just pace yourself for that type thing, but just allow yourself to feel all the things. What do you need to go through? What do you need to work through so that you can feel comfortable and feel like, okay, I can take this piece. In fact, we were just talking about it literally today because, so Michael uses the bathroom sink and drawers and all that that were Ryan's. And so I've cleaned everything out of it before Michael moved in here permanently. But for a long time, Michael shared closet space with Ryan, Ryan's old cowboy hat was in there still.

(00:41:21):

And Michael's just was so great at being like, that's all right. Just hang my shirts up here next to Ryan's old cowboy hat or whatever else is in there. And finally, when he moved here permanently, I was able to get everything out of there. I wanted it to be his closet, his space. But just this morning, he said, I was cleaning out some of the drawers of his stuff, his stuff that's in there. But there's one drawer that still has the clippers from, or the, what are they called? The Cheers or whatever that were, Ryan's and I took those out that Ryan used. I took those out a long time ago, but the pieces were still there. I didn't take all those pieces out. And he came to me and literally let me know and asked me about it. We're talking five years that we've been married, and he was still, I took all my stuff out, I cleaned my stuff out, but I left.

(00:42:09):

I left the stuff from Ryan's clippers in there. And so it's still five years later, I forgot all about those being in there. And rather than him just, I would never know if he were to just get rid of them, but it's the fact that he was like, let me her know that they're in there, whatever she wants to do with them. So it's things like that. It's just the slow moving pace instead of just jumping in and being like, okay, I'm ready. I'm ready for the next chapter. There's still pieces years later that are like, oh, that's still, oh, I forgot about that. Or, oh, yeah, I dunno what to do with that. Or we're still going through things together. So that's my advice for widows is just slow so that you can figure out where you are with things and where the person is with you in

Emily Cave (00:42:57):

That. One of the things after Colby dies, I didn't throw anything out. That was one of the best widow advice I was given is just give it some time because you kind of just want to throw it out. But I remember when I moved here in April in my house in Edmonton with my parents, they're still there. Colby's jerseys are hung up, and his photos, his sticks, all of that. And I remember heading to the airport and I remember seeing his year, and I just felt it was such a weird feeling of knowing like, okay, I'm moving to the states now and all of that, and I wasn't bringing his year. And we haven't kind of decided what to do leaving that all in Edmonton, but I felt like I was leaving him behind. And I just remember sobbing at the airport and I was such a bittersweet feeling, you're excited for this next chapter and going to the us, but even like you're saying five years later when you come across stuff, you're slowly transitioning into this new marriage or relationship. There is things that still hurt and will always hurt. So it's so amazing that Michael even today gave you that space to just let you know or think of letting you know about Clippers where I feel like a lot of people actually, other than my parents and my close friends, would never think, oh, Emily's leaving behind Colby's ashes or Colby's belongings to move here. And what that may make me feel during that already big transition

Michael Bolton (00:44:58):

Sounds difficult, I guess for me, just listening to you ladies. Yeah, for someone who's dating a widow, I mean, obviously we were older and I do believe that helped having some more wisdom and still a long way to go on the wisdom, some wisdom and understanding of life, I guess. And I would just go and say, what you girls have just said, you give more time. You need to be able to give time. You need to be able to step back and let the widow and her family have those moments. Because if you think that you're going to date a widow and then the memory of the other person is going to go away, then you're feeling yourself. It's not the keyest. So you need to be aware of, if you're going to data a widow, you need to be aware that this is a lifetime thing, that that person is going to be part of who you are in your marriage, and you need to be compassionate.

(00:46:09):

You need to be compassionate and have patience. And yeah, just all those things. I'm not just saying those words just randomly off. I do genuinely mean not, you need to realize that there's actually three people in this marriage, and that's how I look at it. You know what I mean? I know Ryan isn't physically here. I have a lot of respect for him and who he was, even though I never got to meet him. I've heard lots of stories. It's about being respectful. And I again, and I'm grateful that I get, I get to love Jen. I see Jen as my wife and I, like every man should be treating his wife. I adore her and Ryan as part of who she is. And also we are situation with the kids. The kids need space. I mean, when I came into, I'm sure for them, when I came into this situation, it was a whirlwind. They're like, who's this guy? You know what I mean? Well, not only is he from Ireland, but he made me try to replace my dad. You know what I mean? Which is never something I've ever tried to do. Just the normal things you would think of as a teenager under from a widow family. I'm grateful that my relationship with the kids has really grown. They know I'm not their dad. I never expect them for me to be their dad. Do you know what I mean? And Ryan is their dad, and I respect that.

(00:47:38):

And I guess it isn't a lighthearted thing to deal a widow. It's not something to be taken lightly. It's serious business. It's like, yeah, there's a lot. There is going to be anniversaries obviously every year. Just again, you need to be mindful. And for me, if you're going to go with did in a widow, then you need to embrace what the grease that the widow carries every day and be part of that. And the joy is being able to be part of that. Not that there's any joy in what was lost before, but just to be able, that's what makes us a family that brings me and Jane closer together and understanding. She's an understanding of my past of we all have a past. So it's just about fundamental basics of marriage as well. I

 Jennifer Osler-Bolton (00:48:35):

Love

Michael Bolton (00:48:36):

Yeah, I know.

 Jennifer Osler-Bolton (00:48:39):

If you love someone, then you love all of that person,

(00:48:42):

Everything. And actually as you were talking really quick, another thing that I thought about for widows going into dating, because I can't really offer advice on how to date a widow, that's where he comes in. But for the widow dating, I would say that the biggest thing also is to not let go of your standards. To not settle out of either fear that you won't be loved or fear nobody can love you or worry that it's never going to happen again. We tend to lower our standards because we're just like, well, it's probably as good as it's going to get, because we know as widows we're difficult to love. A healthy widow knows that she's difficult to love. We know that. And so we can end up in fear being like, no one's going to be able to love me. No one's going to be able to whatever.

(00:49:29):

Okay, fine. I'll just take this guy because he is nice right now, or whatever it might be. But because we do come with such a complexity about us, it's all a reason not to lower our standards. As far as, I think, again, widowhood is a weird balance. It's the standard of I need someone to come in and love me and love the memory of my late husband and love this part of me. And if we have kids, love my kids and all that kind of stuff, but then also be able and willing to be like, okay, but then I'll also step into this new realm with you, and I'll love you too, and I'll love whatevers. But that's where that standard is, is someone who will love you through that. Can you love me through that while I'm figuring this out? Because I don't know how to do this.

(00:50:11):

I don't know how to balance both worlds. So can you love me through that? And if the gentleman in mind is not able to do that, then my strong advice and for a widow at that point would be then you've got to evaluate what your standards are. Because widows are so worthy of being loved and being loved. Well, and the men that were before, the men that were here first, they are equally as worthy of being loved and being remembered. And I think anybody who's alive, we would want to know that we are remembered. I can't think of anyone who would be like, well, sure, when I die, I hope everyone forgets about me and nobody talks about me ever again. That's insane. That's insane. And so if we know that about ourselves, we can't expect a gentleman can't expect a woman to let go of that memory and that legacy because no doubt he would want to be remembered the same way. We don't ever want to leave this earth hoping that we're forgotten about. That makes total sense,

Emily Cave (00:51:15):

Both. Well done. Okay, last question. So both of you as parents, Jen and you particular just as a mom and being the one know, but Michael, obviously curious on your opinion, if your child, so Michael, your two daughters, or Jennifer, your son or daughter, wanted to date a widow. Now being a widow yourself, Michael, how would you feel about that? Would you be worried? Would you be concerned? How would you support their decision?

 Jennifer Osler-Bolton (00:51:55):

I wish I could answer this without being a widow. I wish I could answer it with a non-biased opinion behind it, but I'm highly biased behind this because I do have a son. I have a son, and I've watched him go through this trauma losing his dad. And we actually, him and I just spoke the other day, and I said, everybody in the world has some sort of trauma they've gone through. It may not look the same as ours. It may not even be in the same realm of what our individual trauma is, but everybody's gone through something that has hurt them. And so for me, for my son, I've seen him become a very empathetic teenage boy. He's a tender boy. He's sensitive. So when I think about that, I actually feel like my son would do well with someone who's gone through trauma because he would know how to love them.

(00:52:49):

He would know how to show up for them. And also because I've been able to teach both of my kids how to walk through trauma and grief and that sort of thing, so they know how to respond. Grief doesn't scare them. Trauma doesn't scare them. It's impacted them greatly. And so I personally would not have any issue with my son coming into a relationship with a widow especially. And even for my daughter, I wouldn't have an issue with her getting into a relationship with a widower, because we do come from a unique perspective of we will make sure to honor your person. We will make sure to honor your people because we know how it feels and how desperately we want

Emily Cave (00:53:32):

Our

 Jennifer Osler-Bolton (00:53:33):

People to be remembered. And my biggest fear after Ryan died actually had nothing to do with me. My biggest fear after Ryan died was that he would be forgotten. And to this day, if I give one inkling that somebody's slipped up and forgotten about him, I'm all over it. I am just,

Emily Cave (00:53:49):

Oh, I feel you. I feel like you're so protective. I

 Jennifer Osler-Bolton (00:53:53):

Just went through it. His anniversary was three weeks ago, and I just went through it. I was like texting someone and, excuse me, excuse me. I'm noticing something here. I'm noticing a lack of something, because that was my fear. I don't want him to be forgotten. And so I can appreciate that if my kids were to enter into a relationship with somebody who lost a partner before them, I know for a fact that my kids, they know that fear of their person being forgotten. And so they would do well to honor that. And not to speak on Michael's behalf, but I think with his daughters, because his daughters obviously don't know that trauma in the sense of physically losing a parent. But they've watched Amanda and Brandon go through this, and they've watched me go through this, and they've watched how their dad has loved on me and walked through stuff with the kids. And so I feel like even having that exposure to watching someone go through that grief, I feel like they would be amazing partners to someone who, God forbid, was a widower. They would be able to see that. And I think there is something for people who have never experienced this, to act as though they know how they would do it is, well, I have a lot of words for that, but it's just, it's not appropriate. It's not appropriate.

Emily Cave (00:55:08):

It's so interesting, whether it's a parent or friends or family, I find, I mean all widows, we kind of talk about it, or it's the Instagram trolls, people thinking that they would know exactly what to do had it been them. And I feel like widows have so much pressure on themselves and are actually really hard on themselves. So for me, I always say, you can't fault someone who's not gone through trauma. I can't be mad that someone hasn't gone through the trauma that I have, and that's why they don't understand it. However, that doesn't take away the hurt when they pretend that they understand it or cast judgment, whether you're, whoever you are, trolls, whatever. So that's why I'm curious from a widow perspective and marrying and parents and all the different aspects are friends, your guys' depending on it. What about Michael?

Michael Bolton (00:56:09):

Yeah, just I, being Amman and very practical, always talking practical. Jen's a compassionate one. Really. No, I guess I would just make them aware. As I said earlier, this person has been through a lot. You need to be compassionate. You need to be understanding there's going to be moments in your marriage or in this relationship that your job is going to be the top priority. You know what I mean? Because I respect Jen saying that should be that effort to make me feel first. But there are days where Ryan is put first in the family, and that's fine.

(00:56:49):

So there's going to be days where you're not always the number one person. You know what I mean? And that's good. That's fine. It's a unique situation. Yeah. It's not just a normal relationship. There's a lot. There's there. But also as well, that every part of it is possible. It's not something to shy away from. It's not an obstacle that can't be worked on and actually turned into a lot of joy. So yeah, I guess for me, it would just be giving them an awareness to kids of what might be ahead. I'm grateful in our relationship that Jim and I have a lot of harmony between ourselves. So I think that is in turn helps a lot of, I know I could picture in some way if we weren't in such great harmony like that, there could be a lot of arguments. I think there's potential to be a lot of arguments.

(00:57:47):

So there's potential for so much jealousy. I can see that. I'm sure there are times where I could have turned around and said, Hey, you stop posting about Brian, or Will you stop talking about Brian? But that's with the understanding that I have of all the stuff we've talked about then that has enabled me to have, I guess, a compassion of that's what Jen needs than rather than it's about me. It's not all about me. And that's where it comes down to, it's not about me, it's about us and about our marriage and about what Jen needs and at times about what I need. It's not all about Jen and what she needs. I need stuff at times as well. So I think whenever you have that compassion for each other and that understanding and harmony, that just makes things better, easier. Those times where it could be very difficult are made easier ever. Making sense.

Emily Cave (00:58:44):

No, that makes sense. That totally makes sense. Literally, I could not have found a more perfect example of had a widow and how to be a widow. I feel like Jen is my go-to

Michael Bolton (00:59:00):

Yeah. She hug you a lot as well

Emily Cave (00:59:02):

In life. And I am, yeah, lucky to know you both.

 Jennifer Osler-Bolton (00:59:09):

Well, Emily, we're super lucky. Know you. But honestly, I had a thought while Michael was talking and I was thinking that there's a potential for people who have never walked through this to experience something firsthand, to be a part of it firsthand. Even if, obviously Michael wasn't a part of it when Ryan died, but he's a part of it now. And the chance that's there for people to walk through this with you, to become better people as a result of it, to watch you go through it, to learn about it, to take the time to learn about widowhood. We actually, as widows can offer an opportunity for people to gain understanding and compassion about a trauma that prayerfully, they won't know until they're very, very, very, very old. It's kind of like we went first in a sense to teach people or help show people how to be compassionate. And so with what you're doing, Emily, you have truly the opportunity and the ability to change the lives of people around you by allowing them to learn about compassion and to learn about what it means to love someone through all of their trauma. And so anybody who has the ability to have a firsthand experience with you is extremely, extremely fortunate because it's a chance to become better people with what you're doing. So thank you for giving that opportunity to so many people. Well, thank you.

Emily Cave (01:00:30):

I try to fulfill the vow I made Colby in that hospital rim. Yeah,

 Jennifer Osler-Bolton (01:00:39):

you will change the world.

Emily Cave (01:00:44):

As you guys can see, Michael and Jen have such a beautiful relationship and one that I admire so well. One of the things that I love most just watching their relationship and having this conversation with them is how protective Michael is over, not just Jen and the kids, but also Ryan and his legacy. I feel like he is selfless and handles it all with such grace, and I am just so thankful that he loves my friends so well. And also honors Ryan the same. So one thing that I've learned since starting this podcast journey is that the first few episodes are a really big deal, so I would totally appreciate if you shared, rated, commented, send to friends. I'm so excited for the future special guests that are going to be on the podcast as well, I do want to address on the UMR podcast, we're going to talk about a lot of things.

(01:01:42):

This episode was about grief and it was about widowhood, but there is going to be episodes that are about joy and other people's stories that haven't experienced widowhood but have overcome obstacles themselves and that have shown that they are more than what life has thrown at them. And hopefully remind you or relate to you in whatever your situation may be, that you are more to. I hope you guys follow along with us journey. Please forward this episode to one friend, and here is your reminder, my daily motto, be somebody that makes everybody feel like a somebody. So go this week and make someone feel like somebody and remind them that you are more.