Being There for a Bestie in Grief: Navigating the Holidays Without Losing Yourself

Being There for a Bestie in Grief: Navigating the Holidays Without Losing Yourself 

Description:
The holidays can be magical… until they aren’t. When your bestie is grieving the loss of her person—whether a spouse, partner, or the anchor of her family—the season hits differently. Suddenly the twinkle lights feel heavier, the memories sting sharper, and the pressure to “do it all” gets complicated. You want to show up for her, hold her together, make sure she doesn’t feel alone. But you’re also juggling your own family, your own joy, your own traditions—and sometimes it feels like you’re being stretched between her grief and your life. 

In this episode of Slightly Unsupervised, Jennifer and Jackie get real about what it truly looks like to support a grieving best friend during the holidays. They talk about showing up with compassion without abandoning yourself, why checking in matters more than saying the perfect thing, and the delicate balance between honoring your own traditions while making space for hers. 

From navigating emotional triggers to understanding what grieving friends wish we knew, this episode is your gentle guide to loving her deeply while protecting your own heart. Because you can be her anchor without becoming her life raft—and sometimes the most powerful gift is simply, “You’re not doing this alone. I’m here.” 

In This Episode:
💛 Why the holidays hit grief differently than everyday life [01:00]
🤍 How to show up without overstepping or smothering [05:10]
🎄 Balancing your own traditions with her emotional needs [12:00]
📩 What real checking-in looks like (and why it matters) [14:45]
🕯️ Why talking about the person they lost is often exactly what they need [17:00]
💞 The best gift you can give a grieving bestie [21:00]
✨ Bestie Rapid Fire: Holidays, healing, and the little moments that matter [23:00] 

🎙️ Hosted by Jennifer & Jackie
 💍 Presented by Bestiemony™ — Because not all soulmates come with a marriage license.
 ✨ Part of the Chickology™ Podcast Collective 

🎵 Closing Song: Definition of a Best Friend by Brooke August & Hannah Rose
Follow Brooke on YouTube: @brookeaugust 

If this episode hits you in the feels—or helps you love your bestie a little softer this season—send it to the friend who holds your heart. 

🎧 Subscribe to Slightly Unsupervised for more real talk, deep laughs, and the truth about modern friendship. 

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Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.

This episode of Slightly Unsupervised was brought to you by the creators of Bestiemony®—the original friendship ceremony that proves soulmates don’t always come with a marriage license. Hosted by Jennifer and Jackie: best friends, business partners, and co-founders of the movement celebrating real, ride-or-die love.

💍 Book a Bestiemony: rhinestoneweddingchapel.com/bestiemony
📱 Follow us on Instagram at @Bestiemonies
📩 Got a bestie story to share or a subject request? Email us at ChickologyPodcasts@gmail.com

Transcript

Jennifer 0:00

Hey there, I'm Jennifer, and I'm Jackie. And welcome to Slightly Unsupervised, where best friends, business partners, and the chaos behind testimony, a ceremony we created to celebrate the kind of soulmates who don't come with a marriage license.

Jackie 0:12

This podcast is all about that friendship energy, the deep stuff, the messy stuff, and the laugh till you snort stuff.

Jennifer 0:18

So whether you're driving, folding laundry, or hiding in your car for some peace and quiet, you're in good company.

Jackie 0:24

Let's get slightly unsupervised. Okay, today, today's episode, being there for a bestie in grief, navigating the holidays without losing yourself. The holidays have a way of shining a spotlight on what and who is missing. And when someone you love has lost their person, the season can shift from a magical to a painful overnight. If you've ever had a best friend lose a spouse, a partner, or the anchor of their family, you know the heartbreak of wanting to hold them up while also holding up your own life. You want to be there, you want to show up, you want to make sure she doesn't feel forgotten or alone. But you also have your own home, your own family, your own traditions that matter too. And sometimes it feels like you're being pulled between your life and her grief, between showing up in a way she desperately needs and remembering that you're allowed to have joy, celebration, and boundaries too. Today we're talking about what it really looks like to support a grieving bestie during the holidays, the practical ways, the emotional ways, and the ways that don't require abandoning yourself in the process, because the truth is you can love her deeply and still honor your own season.

Jennifer 1:30

So we decided when we were talking about doing our uh podcast during the holidays that we should probably touch base on a few holiday subjects that could come up for besties. Um, and we actually have a friend, one of our other restaurants, uh, lost her husband a few years ago, maybe a year, maybe two years ago. I'm not sure how long it's been. You know, how to how to be there for your bestie when they're grieving, in particular during the holidays, because I think the holidays really drag up a lot of memories of time together. I know it's a specific time that we all spend together, so they can be a little more triggering than just everyday life. And how to really find a balance between having your holiday and being a good best friend, and then letting your best friend know you're there and you're supporting them, but also enjoying your own family. Um, snow is hard to, I'm sure, find a balance on that. That you, you know, you wanna, at least I do, I want to rescue everybody. Like, oh my God, we got to take care of you now. So I think our friend that does it is that has the situation is very good at balancing her life. And I think that she probably does okay with it. Um, I think her friend feels probably very supported by her as well as she keeps her own family together and does her own traditions as well. I know she's one of those people that invites you over for everything. So I'm sure that that's been very helpful in that process that she's, you know, they have a lot of events that go on at their house. They're very social, so they probably have her over quite a bit. And she probably needs that. I know when when this thing happened to her, I I was telling my girlfriend, I was like, look, it's it's she's in shock. This is really like it's gonna take a long time. People grieve for a long, long time, and it's not something that she's going to bounce back from for years and years. And that, you know, it's gonna be hard to navigate that because at some point everybody's life goes back to it. It's you know, when somebody dies, I know it's a lot of concentration on that person and that situation. And then, you know, after a while, you kind of go back to your life and back to everyday life that we all have. Your friend is still in their complete grieving process. And uh, you know, it's it's an ongoing years and years of grief that happen with this sort of thing, especially when something so tragic happens. Have you had any friends, Jackie, that you um have lost or partners that you've had to support while you know, just yeah, not female, but male.

Jackie 4:07

Male. Yeah, yeah, yeah. That we've had to do that. And we're there, yeah. Like for I guess also other like special occasions like his birthday. Right. Normally she would do that kind of stuff. So we try to help him with that. Um Yeah, and it's uh with our friend that we're talking about too, there's they live so close to each other and they did every uh almost everything together too. Right. So I mean, so at the same time, our friend's family's grieving also, but and you know, and and so is the wi the wife who whose husband passed. But I'm sure like that brings a lot of stuff up for them too, you know, having them over, like for the tamale day they just had, you know, having the all of them over. Right. So um, I think about that too on them. Yeah. Because they do spend so much and their daughters are all close, you know. Right. And we're like um talking about my friend that, you know, we helped after his wife passed and Stefan was trying to be there all the time. But he also has where he's he's we weren't with him as much. Does that make sense? So I could see where a difference is for them, um, just because they did so much as families together too.

Jennifer 5:18

Right. We yeah, our our friend that we're talking about, her daughter's daughter and this lady that we're talking about that we're talking specifically about her daughters, their daughters are best friends, and then also not only that, the husbands were friends. So it was like a family loss and a family, you know, I know it was very shocking and it was shocking to me. And I'm on, you know, 500 miles away, so I can imagine the loss of them in the situation that they were in. So, but there's these are she's not the only person this has happened to, and this is kind of always one is touch base on this that how do you be there for your best in grief and navigate the holidays without kind of losing your own your own way in that? So just some of the things that that you know you can do is consistently check in, um, you know, thinking of you, but going further and letting know what you need is always nice. I mean, I think, and I maybe you're this way too, Jackie, but like when somebody dies and you want to say something, you're almost like you don't know what to say. And it depends on, you know, if it's the dog, if it's the husband, if it's the child, like you don't know. Like you you're kind of at a loss of words about that because I know until you've been through it, you don't really understand that side of it. So you just kind of stand there like, oh my gosh, I'm so sorry. But it seems so minimal, and yet we don't really know what to say to people because we may have not experienced that yet, or we may not have the emotions to understand it. I know once you've been through it, you understand it much better. But when you're not going through it, I know we get kind of paralyzed with that. You know, how are you? I know I check on her occasionally I'll see something and I'll send it to her via Facebook Messenger or something. I'm like, hey, I saw this, I was thinking about you. But acknowledging it, I know a friend of mine, uh, actually a guy that I worked with, I was very close to, is younger, but he passed away. He had a drug overdose, and his mother and his father, I knew them, and she had to call to tell me. And I mean, I was devastated. And they were the sweetest people, but what they kept saying to us, no matter what you said, they were like, we know he loved us because you're like, oh my god, God, he loved you guys so much. It's just like I know he knows that. But what she wanted was us to spend time with her. She was like, if you guys could just come over and let's talk about him. Like, she never wanted that's what she needed from us. And we weren't like that close to her. We had never been over to her house. But another friend of mine and I went over and we would just talk about him. We would just talk about how we worked with him and all the things he had and and tried to just, I know it gave her peace to talk about him and to laugh about him. It wasn't all grief, it was like, don't forget him. Like that's how I felt he wanted us to remember him. And she wanted us to hear, she wanted to hear what we thought of him, all memories we had with him. And I always remember that. That's like so impactful because, like I said, when somebody loses somebody, I feel like we get into this like space of like, oh my god, they need to be a we need to tell them where we know we're we're there for them, but we don't want to bother them either, right? Like, you know what I'm talking about? Like, do you have that feeling?

Jackie 8:34

Well, just set up what they say with women too, that um a lot of grieving women isolate too.

Jennifer 8:40

They do.

Jackie 8:41

And so if you're isolated and they're isolated because you don't know what to say to them, because I remember like not knowing what I what I should say and not to say, you know, after the passing of our one friend. And like even talking to her daughter, I was just like, okay, what does she want to hear? And then she she said this, she did a story little vlog thing at one point and says, I want you guys to talk to me about her. And it was the same thing. She's like, I want to remember her. I want to all the good stories, the fun stories, and don't feel like you can't talk about her to us anymore, you know. And but I do remember her saying that and actually letting people putting it out there to please talk to us, like my dad, like me, my sister, we we want to talk about her. Right. You know, we don't want to the kids to forget her, you know, because they have little ones. And so the little ones, you know, like she even made pillows with Colleen's face on them so that the kids will always have those pillows because they were so young when she passed. So she's like, I want them to see her, you know. Remember her. So I think that's I was happy that she put that out there because, like I said, it was hard. Like you just don't know what to talk about.

Jennifer 9:50

Well, I think what you yeah, I think what you try to do, maybe we all do it, is like if we don't talk about it, they're not gonna feel bad about it.

Jackie 9:58

And I think what happens is crying, or yeah, exactly.

Jennifer 10:06

You're like, let's talk about anything but that. And then in the meantime, what you've done is hurt them because what they really want you to talk about, I at least have come to that experience is to talk about them because that that gives them um day, that gives them puts it back in their memory, like a good thought back in their memory. So it can be tricky. I know grief has its own way of dealing, you know, grief goes through phases for different people for different ways. But what I've run into is that the one thing you don't want to do is not acknowledge it. Definitely just like you would in everyday conversation, just have conversations about them and talk about them and laugh about it and remember it the way you always remembered it. And I think that, you know, what I find is people in grief find that to be comforting to find somebody that wants to talk about that person with them and let them. And, you know, there's a dance to that. You can't can't wallow in it. You can't, you gotta keep it kind of uplifting, I think. And, you know, it's just a tough one. It's a tough one to know when you don't move in through it. But, you know, some of the things that, you know, that they say was is to check in and then, you know, and then give options, you know, kind of offer some options instead of like expectations, like, hey, do you want to come over for dinner during the holidays? Do you want to be over here? Do you want to go over and wrap presents with me? You know, do you wanna do you want me to go with you shopping? Do you need some company? Or do you need a quiet night in in or something? So you're giving them options to, you know, pick whatever it is that maybe sound like they can get through. And sometimes you maybe need an option where it's just the two of you, like dinner. Maybe it's an option where you're going out in public, like shopping. Maybe there's a option with do you not want my involvement tonight? Do you want a quiet night to yourself? And that kind of is the full circle. It's like which which of those might maybe is the most appealing to you, so that you can kind of give them opportunity to kind of decide. Yeah. And then, you know, there's there's always the person that says, Yeah, let's do it. And then the minute comes around, like, I just can't do it.

Jackie 12:12

You know. And that happens. Yes, definitely.

Jennifer 12:15

You definitely just have to kind of give people that grace and be like, no problem, man, I will do it another time or something.

Jackie 12:22

Yeah, that that does take me back to another friend who passed and like talking to her daughter and stuff, because she ended up not doing a a wedding just because her mom wasn't gonna be there. And so um, there was like certain things, like we'd go down to down to the desert and I'd call her, and there's a couple times she'd meet she'd meet up with us and stuff, and but there was just some things that you'd ask her if she wanted to do, and she's like, I just can't. I just can't do that. Right.

unknown 12:46

Yeah.

Jackie 12:47

But that was her, but she'd be there part of the time. But I would be like, Okay, well, we're coming down, we're gonna do this, we're gonna do that. So, you know, you choose what you want to do.

Jennifer 12:53

Yeah.

Jackie 12:54

But I did find her where if there's a lot of stuff that if it was something that her mom that they did a lot, or if us three had done it together, she kind of like she got better longer after the passing. Right. But at first it was just like it was hard for her. She right. So she picked and choosed her stuff. Right.

Jennifer 13:13

Oh, yeah. I I think there's a there's a vast difference between the first holiday season than the second, the third, because you've now have some new memories with, you know, imagine the first grouping or the first holiday after you lose somebody. I mean, every expectation is with them, and then you have a holiday without them. So the second holiday probably is a little bit better, not because they weren't there, but because you have seen how it goes. You know what I mean? You have some basis to kind of go, okay, this is how it's gonna go.

Jackie 13:40

Well, that's like our one friend whose wife passed. She they did a Christmas party every year. And we all knew it was always the first Saturday of the month. So everybody always knew that first Saturday is when they were gonna have their party so don't make any plans. And they've been doing it for 20 something years with all their friends, and then we got added in as we became their friend, you know. And uh, so I I'm yeah, I remember like that first year when they didn't have it, you know, it just kind of made me sad because it's like, and then it's like, do we make do we do one to you know what I mean? And for everybody, but it's like nobody else did it, so we didn't, but it was kind of a bummer.

Jennifer 14:15

Well, you can't you don't know because are you stepping on toes there or are you being respectful? Like, you know, it's hard to know. I mean, again, I I can't express it enough, but to say that, you know, it's kind of a dance in the beginning because you don't really know what to do or how to react or what to say, and you're kind of fumbling around in that. But, you know, the other thing that this thing kind of talks about is though we all, even though someone's grieving, your best friend's grieving, then you still have your own traditions. And there's gotta be some guilt in that, right? Especially in our friend that's really close to this, this other girl that one of our other best sees that, you know, all these things are still going on in your life and you still have all these traditions, and now, you know, feeling like maybe we shouldn't celebrate so much this year, or maybe we need to tone it down a little bit, or you know, and it's you know, they don't talk about that that's a good idea, that you still need to have your traditions. And also maybe it helps people sometimes when you have your own traditions or you bring them in for your traditions, it gives them a new basis of what a holiday can look like. So you don't want to abandon that. You wanna give hope that it goes on maybe a little bit, like you know, you'll go back to it, or you can come over here now or whatever to kind of make them feel. I think, you know, if something happened, I'm sure, and we live near each other, it would be like, well, just come over here and you'll we'll just join in. Like you'll just become part of the new family here and done until somebody else comes around and you move on to something else. But I think I would do that. I would for sure drag you over to my house and be like, well, come over first thing in the morning. We've got present. You know what I mean? I would probably do that. I'm sure you would do that too, because that's kind of how you are too.

Jackie 16:00

So definitely.

Jennifer 16:02

But not not losing your your own traditions, but kind of giving some space for that is important and balance it out a little bit and be intentional with your scheduling of time with them, you know. Let's give them give them a thought that maybe you are for sure thinking about them. I think that's important to do. And then, you know, maybe there's something they always did that, like you were saying, this Christmas party that they didn't have afterwards. I'm sure that, you know, if you guys had just said, hey, do you guys want to get together and just talk about her? We always do it that first Saturday, that kind of might have been a cool idea too. Like just impromptu, like, let's just meet at the bar and let's just, you know, we normally do it, but let's just talk and let's get together and remember our friend or whatever. So you're not responsible to fix her grief. You can love someone that still has your boundaries and and don't make up for that one person she lost. You can stand beside her through the darkness. You don't have to make it up to her that she's lost somebody, and grief doesn't end when the tree comes down. So for sure, for sure, you gotta keep checking in. It's just there's a very tender spot there that you've got to be really on your game, and you are the main player. You cannot expect her to respond or keep up with that during that period of time. Maybe a year, I would say a year or two. You gotta be the lead on that, don't you think?

Jackie 17:21

Yeah, definitely.

Jennifer 17:22

You can't be mad that she doesn't call you to have lunch or something. Like sometimes you just gotta be the one to continuously ask and continuously get denied until they're in a good spot and not take it personally on any level, because that people need that time to, you know, they need sometimes for you to be that person to them. So, anyways, supporting her isn't about sacrificing yourself, but it is about being consistent, present, and real. And sometimes the best gift you can give someone is simply saying, You're not doing this loan. I'm here with you, right? That would give me such comfort. So, all right. Well, let's move on to the bestie rapid questions. Jeff, go first.

Jackie 17:59

Okay. So, what's one thing a friend did for you during your hardest season that you'll never forget?

Jennifer 18:06

So, my hardest season, I haven't had any losses like that, but one of my hardest seasons was when I got pregnant and you girls showed up for me, and I've talked about it many times, and I'm gonna continuously talk about it, but it's the support. I don't know how to explain it. I just know that to know that that you are supported and loved can do such wonderful things for people. You know, I'm pretty good at it because I know what it feels like to be on the other side. We talked about this grief thing. I haven't been on that side, I don't have the words to say it, but I do have the words to say it when that when you need love and support because I know how important that means to somebody and that you can really change somebody's life with it. What about you, Jackie? Do you have anything that a friend did for you during your hardest season that you'll never forget?

Jackie 18:49

Say probably the the first year of divorce with my children, you know, being alone with them, because my parents don't live in California. They were gone. So I would say, and it wasn't really, I guess like my sister-in-law, my brother, because they were still here and they were there for me. Yeah. So they were very supportive. Yeah.

Jennifer 19:08

Mm-hmm. Cause your whole life changed. And even though it wasn't death, it was still a completely 360 on every holiday you'd ever been, or at least up until that point, you know, while you were married to him. So I'm sure that that's, you know, something that you remember too, that somebody stepped in and said, You're not alone, we're gonna do this, you're gonna be with us. Feeling that and taking some of the weight off of you, right? Like, I'm sure that you were probably wondering exactly how it was gonna go and how the kids would react. Like, I know that. Oh, yeah.

Jackie 19:38

And and the first year, um, I for a lot of support from um my ex-in-laws also, because they were in the mountains, so they wanted to make sure, like, took us out on Christmas Eve for dinner, you know, with the boys, a nice dinner to dress up and you know, just to keep it like even though we weren't doing our normal tradition, you know what I mean? Right. Just to keep us busy and to keep the boys busy.

unknown 19:58

Right.

Jackie 19:59

I guess it was a lot of family for me on that. Um, but everybody was far away, and I mean, a lot of people didn't even know I was divorcing.

Jennifer 20:07

Right. Yeah.

Jackie 20:10

I literally sent out a picture of me and my boys and said we've moved and with the address, and that's how people found out.

Jennifer 20:17

Sounds like when everybody found out I was pregnant, got a baby shower invitation. Like, what is going on here? I'm like, oh yeah, by the way. Oh yeah. Because sometimes you drop the words, you can't say it. You it's like uh it's too heavy, I guess. So I get it. All right, what does showing up look like to you? What does showing up look like to you, Jack?

Jackie 20:38

Probably just checking on me.

Jennifer 20:40

Mm-hmm.

Jackie 20:40

Showing up, you know, just asking how I'm doing.

Jennifer 20:43

Right.

Jackie 20:43

And that kind of support. And it's not that you have to be here, but just checking up. Right. I think it's uh showing up.

Jennifer 20:50

You went through a little bit of something when your husband got sick last year. And, you know, I know that we're we as your best friend group, we're trying to navigate that as kindly and as peacefully as we could without overbearing it, you know, overburden you with our needs to know. And we certainly kept in touch with each other behind the scenes to go, okay, has anybody heard anything? Where are we at? Like, because we were very concerned.

Jackie 21:18

Yeah, because I got I got a little withdrawn too. I was like just talking about it, it's like talking to doctors and going to these things. And it was like I just get home and I just didn't want to talk about it or even write a text. It was like, just let me just sit here.

Song 21:32

Right.

Jackie 21:32

You know, take it all in. Um, yeah. So no, you guys did good. Everybody did good. We did.

Jennifer 21:38

We tried our best to sometimes we needed we're like, I we know she went to the doctor today. Well, what's going on? You know, we know we're like, she'll show she'll tell us when she can. And usually you would, you know, like you did, you would send it to one of us or have a conversation with one of us and we would spread it around to the others so that everybody kind of was on the same page so we didn't bother you about it. But um, you know. Sometimes you just gotta sit back and wait, and that's hard. It's hard when you're weird too. So I get that. Um showing up for me looks the same. Just showing up and just keep in touch with me and keep up even if you send me a meme, something that just is like remember I'm my thoughts are with you today, or you know, anything like that is so important.

Jackie 22:20

So okay, you're next. Do you believe one friend can change the way you survive grief?

Jennifer 22:26

Yes, 100%. You gotta lean into somewhere. Um, and if you have small children or you have children, you can't lean too heavy into them because it's uh they've got their own grief, you know what I mean? So you've gotta have somebody that you can lean on and support you for a while. And I do believe that one person can do that for you. So it's having a best friend. We've said that a hundred times. We're women, we're getting older. We know that the best friend thing is important as we get older because typically we live longer than the boys, and we need to be there for each other. So we've already got that plan in place. Okay, what's the best holiday? What's the best holiday tradition you would share with the bestie in pain?

Jackie 23:08

Holiday tradition.

Jennifer 23:09

It just matters about holiday, I guess, too. Yeah, that's true. It depends on the holiday. If it was Christmas though, for me it would be like having a moment. Yeah, you gotta come for Christmas Eve. We have play games and we have drinking, you know, we do games and we're we have drinking to just a light, fun kind of holiday, that particular one. And if you don't feel like the next day, totally get it. Maybe I'll come over later when I get done with my whole family thing and we can be quiet and out or whatever. So Yeah, but you're right, it depends on the holiday. You gotta kinda teeter that a little bit. So if this episode hits you in the field, we consider that a win.

Jackie 23:53

Be sure to subscribe, leave a review, and share it with your ride or die.

Jennifer 23:56

And when you're ready to make your friendship official, book your best emoji at rhinestoneweddingchapel.com.

Jackie 24:01

Because the best love stories don't always come with a ring.

Song 24:14

We stick together, ride or die to the moon, and no amount of space could ever come between us two. The reuniting's like we've never been apart, and every single time we're eye to eye and heart to heart. What you made of me Through heartaches and ups and downs and this life you've stayed right next to me. I've outta make you laugh till you cry. Look at everything under the moon. The definition of it's friend. It's good.

SPEAKER_01 25:16

It's good.

Song 25:24

And we'll keep it to the rest, but ever craft it ain't hate we're writing a story. Everything will keep on going. Do our days and dance and dance and this life stay right next to me. Uh bottom bake you laugh till you play. It's good.

SPEAKER_01 26:22

It's good. It's good.

Song 26:36

Trust that says loyalty. You and me love trust that says loyalty, you and me, yes.