Are You Ready to Start Dating Again?

Dating can be intimidating at any age. But dating after the end of a long term relationship, dating when you are middle aged - that's tough! How do you know if you're ready?  There are a few questions you can ask yourself to get an idea of where you stand and to better gauge if you truly are ready to get back into the game.

Transcript

Hello, my name is Tiffany, and welcome to the podcast Working on Amazing. This is a podcast where we talk about the work that it takes to rebuild an amazing life.

And I'm using that word rebuild because we're specifically designed for women who feel like they're starting over in the middle of their life. A few different things could lead you to feel like that place where it feels like you're starting over.

For me, that was divorce after a 20-year marriage. For my sister, it was the unexpected death of her spouse.

While those two things are very different, the common thing is that all my plans, all my hopes, my entire vision for my future, my dreams all went up in smoke. My future was no longer going to look the way that I thought it would.

And I had to start over. That is a very overwhelming, very itchy feeling. And if that's you, I want to say I'm sorry.

I know what that feels like. But I also know that it gets better, that there is a way to the other side, and you have the opportunity to rebuild an amazing life. You truly do.

I've gone through it and come out on the other side better for it, and I know so many women who have. You are not alone. You're actually in the right place.

So welcome, welcome. I'm so, so glad you're here. Let's get down to today's episode.

Today, we're gonna talk about dating. And specifically, when are you ready to start dating again? So if you've been in a significant relationship, I was married for 20 years, my sister was married, her spouse passed away.

How do you know when you're ready to start dating? Like, as soon as I got divorced, I knew I was not ready. It's this thing, like, I don't want to dip my toe in that water and then get in a relationship and go, whoa, too soon, got to back off.

How do you know that you're ready? So let's talk about it. Let's talk about some things.

Now, before we get in to some questions to ask yourself if you're ready to start dating, I want to say, if you don't want to date, that is okay.

If you've gone through a divorce, if you've gone through the death of a spouse, and you're just like, no, I don't want to be in another relationship. That is not something I want.

I'm here to tell you, that's a totally valid choice, and I support you in that. I wanted companionship, and I think there are a lot of people who do, so either way is okay. But I knew I wanted to share my life with somebody.

I'm a people person. I want to be around people. I need to talk to people.

So I knew that I wanted a relationship. But like I said, I was very unsure about if I was ready to cross that bridge again, if I was ready to start that. So let's talk about how do you know if you're ready?

And this by no means is a definitive list, but I'm going to give you four things to ask yourself that may help you gauge whether you're ready to start dating again, like get back out there. And it's intimidating. It was not fun.

I don't feel like when I was 20 and in my late teens and in college, I never really loved dating that much. Like that just wasn't my thing. I think there are girls that truly do enjoy it.

But then it was so intimidating to start dating in my 40s. Like that just felt so weird and uncomfortable.

So if I was going to start this process, I wanted to know that I was actually ready, like not dip my toe in that water and pull it right back out. Like, nope, not ready now.

So I'll be honest with you, the first thing is kind of a gauge, are you ready to start dating again? I actually Googled not too long after I got divorced. I asked, like, how do I know if I'm ready to start dating again?

I like put that in Google, for real, I'm not lying.

And the result I got back then, I don't know what it says now, but back then, it was a bunch of different relationship therapists, kind of came to this consensus that you needed to wait one month for every year you had been in a relationship.

So I had been married for 20 years. That means I needed to wait 20 months before I started dating again. That's well over a year and a half.

It felt like closer to two years to me. I ended up waiting two and a half years. And I thought that was what felt like appropriate to me.

This rule is not hard and fast. I believe if you meet somebody and sparks fly, and it hasn't been the full amount of time, but you've had time, that can be okay. If you wait a little bit longer, that's okay.

But this just kind of gives you a timeframe to gauge it. And I remember when I looked at that, I thought it felt closer to two years than a year and eight months. It was like, 20 months, that's a long time to be alone.

But I needed every bit of that time. I needed that time on my own to do things by myself, to heal, to grow, to know that I could make it on my own. I needed to prove that.

I had had my own apartment before I had gotten married. I got married so young, I was 21, but I had still had my own apartment before I had gotten married. When I was at college, I had an apartment.

So I felt like, yes, I can do this. I'm, you know, whatever, I'm capable. But after having been married for 20 years, and then I had these two kids, starting over on my own was really, really intimidating, really intimidating.

And taking the time to do things, and know that I had the ability to do it, was really encouraging, and it built my confidence a lot. Handling things like when the car broke down, taking it to the auto mechanic.

I don't know about you, but for some reason, that really intimidated me. I feel like they speak a different language than I speak. I don't understand half of what they're saying because they're talking about things that I have no grid for.

And it's always expensive. But I did it. And the car had a problem, and I took it somewhere, and I got it fixed, and it was like, you know what?

I can handle this. I can do this. Same thing when the air conditioner, one day in the middle of the summer, and it is hot in the summer, and the air conditioner didn't work, and I called the HVAC, and I was so intimidated.

Like, how much is this gonna cost? What am I gonna do? But they came, and they told me what I needed to do to fix it, and I, I mean, they fixed it, but they told me what the problem was, and I paid for it, and it was like, you know what?

Even these things that have intimidated me, I can tackle them, I can find a way to make things work, and that built my confidence, and it built my self-esteem to know that I could go through life, and problems could come up, and I could solve them.

And so, taking that time to be on your own is good. It's good, because it lets you breathe. And I mean that in a, I don't know what kind of way, but sometimes when you've been in a relationship for a long time, you just kind of need to breathe.

And it doesn't feel good, and you gotta sit with some pain and some anger, but you don't need to do that with another person. You gotta be, you gotta take some time to yourself and figure out who you are again.

Because when you morph into a relationship, somehow you become part of them a little bit. And when that relationship is over, you almost have to rediscover different parts of who you are.

And I think that's just naturally the way we add in flow in relationships. But taking some time, I think is really important.

So I think that just gauge of one month for every year you were together is just kind of a rule of thumb, a little bit of a guide. So if you're asking yourself, am I ready to start dating? And I said I would give you four things to think about.

Has it been enough time? Have you spent one month for every year you were in your previous relationship? Have you taken the time just to breathe and to heal and spend some time on your own?

So has it been enough time? The second question, I think, you should ask yourself if you're ready to start dating or not. The second thing is have you dealt with or come to terms with the way your previous relationship ended?

Now, this is going to be very different for different people. So like I said, I got divorced. The way I came to terms with that and the way I dealt with that is going to be very different than, like I said, my sister lost her spouse.

She's going to come to terms with that in a very different way than I am, because they're two drastically different things.

But for either one of us to enter into a new relationship, we have to come to terms with how that last relationship ended and be at the place where we're no longer seeking closure. I no longer am seeking closure about how my relationship ended.

I've come to terms with it. I've dealt with it. So when I say, I've dealt with it and I've come to terms with that, please don't misunderstand.

You can still have emotion and feelings about your previous relationship. And once again, I'll use my sister as an example.

With the death of a spouse, I can't imagine at any point in the future that she will reach a point where that doesn't feel emotional to her, that she lost her spouse.

That does not mean that she can't have a fulfilling life, fulfilling relationships, fulfilling future. But there's going to be emotion there. But have we dealt with it?

Have we come to terms with it? Are we no longer seeking closure? Okay, so this is where I'm going to say, counseling might be an option.

I think a lot of us could benefit from counseling. I went to counseling. I talked through some of these things.

I think it's really good. One really positive thing that's come out of COVID is that it's so much easier now to connect with a counselor, because you can do it on your phone instead of having to take time off work and drive to a physical location.

So the options of how you can get help have shifted and become much more flexible. I think also, because of the day and age we're in, I feel like our society is much more accepting of mental health, good mental health, you know?

And so I think many more insurances are offering to cover counseling. So I think it's more accessible, and it definitely should be something you think about or maybe look into. Is it accessible for me?

How much would it cost? Is this an option? Is this something that would be helpful?

Another thing that may be helpful is a lot of times there are group share for different situations. So I went to Divorce Care, and that is a group session. We worked through a workbook together, but everybody in the group had been divorced.

And it was all working through that, those feelings and the issues, all the junk that surrounds that, right?

And it was a group setting, so there was some camaraderie and common ground with other people who were going through what I was going through. Similarly, my sister has, there are widows groups and grief share groups and things like that.

Another possible option is, I know Facebook has a lot of groups, so I'm a part of some divorced women's groups, even just on Facebook. And let me tell you, there were some days that those groups were very comforting to me.

I could get on there and I could say, I just got my finalized divorce papers in the mail. And other people would chime in, oh, I'm so sorry, and I know what that feels like. And I was able to voice what I was going through.

It just wasn't pinging around in my own head, you know? I was able to get it out. And other people were able to offer encouragement, and that was good.

When I wasn't able to go to divorce care, because that was only one night a week, I could sometimes find a group like that on Facebook, and I could say, this was a really bad day.

And other people could support me and say, I know what that feels like. So finding groups or a counselor could be a really good option to help you deal with and come to terms with the way a relationship ended.

I will say, sometimes we feel like we've come to terms with something in our own head, the way we view this thing. We're like, hey, yeah, I'm good with it. I've come to terms with that.

But do you know anybody in your life, a friend, family member, maybe? And they would tell you they've come to terms with something in their life, and you know they have not come to terms with it. Sometimes, we're not the best judge of ourselves.

So the other thing I would say is, if you feel like you've come to terms with it, but you're not 100% sure, you think, well, maybe, maybe not, maybe ask a really good friend or family member, hey, can you help give me some perspective here?

What do you think from an outside opinion?

Definitely, if you started counseling, or if you're in a counseling relationship, a counselor would definitely be able to tell you where you are in the list of coming to terms with it on that timeline or on that scale, like, yeah, you're doing really

good, you've really come to terms with it, or you know what, you might still have some work to do. Both are valid and okay, but you really just don't want to start a new relationship until you've really come to terms and finished that old

relationship. You don't want to still be dealing with junk from your past when you're starting something new. Does that make sense? So if our first question, am I ready to start dating again?

Have you had enough time from your previous relationship? How long has it been? And then the second thing, have you really come to terms with, have you dealt with the way your last relationship ended?

Okay, the third thing I think you need to ask yourself is, are you financially secure? And I know some people may take issue with this, and there are exceptions to this rule or advice. I get that, there are always exceptions.

But to the best of your ability, if you are able to be independently financially secure, you need to do that before you start dating.

Knowing that you can manage your budget, knowing that you can take care of all your bills, knowing that you don't have to depend on anyone else, is not only empowering, but so much more. I mean, it builds your confidence. This is the thing.

If you are living paycheck to paycheck, if you are in debt, and you start dating somebody who has an amazing, really, really good job, right? It's gonna be hard for you to look at that relationship objectively. It just is.

So, if you can take care of yourself, then you're not making decisions based off finances, because you've got that taken care of. Now, please understand that I'm not talking about living in the best house or driving the best car.

I lived a very modest life, me and my two kids. We lived in a 1950s small bungalow. I drove older cars.

I did not live a lavish lifestyle, but I lived a lifestyle I could afford. I owned my house outright, and I owned my car, and then my daughter's car, she had to have a car, she started driving. I owned both of our cars outright.

I had zero debt and I had a fully funded savings account, which is at least six months living expenses. I didn't live a lavish lifestyle by any means. I lived a very modest lifestyle, but I was able to put money in savings every month.

I didn't need somebody to come in and take care of me. I could take care of me and my kids. I had it.

I wanted somebody. And because I lived a lifestyle that I could afford, when somebody came along, it was because I wanted them, not because I needed them.

And taking the time to be disciplined and good with your finances positions you better when you were dating. It really does. It positions you better for life.

I just feel like it's an important life skill. I really believe that women especially should really focus on their finances and learn to win with money. I feel like it's so important.

But especially when it comes to dating, you just don't want to be in the position where you think, well, he can help with this bill, or well, if we moved in together and he paid half the bills, that would make a big difference.

I really want you to be able to handle it all on your own. And then when somebody else comes along, they add to your life. They're not rescuing you from a bill, or a debt, or a payment, okay?

It's so important. And like I said, I understand. Somebody walks in, sparks fly.

There's no perfect time. I get it, I do. But if you're able, to the extent that you're able, really, the time you're taken to just be single, really focus on your finances.

Really work on that self-discipline when it comes to your finances, so you can win with money, so that you don't have to make any decisions based off that when it comes to your heart. Your heart should be your heart.

Money should be in a different category, right? And you don't want to get those mixed up. You want to be able to handle your finances and handle them well, all right?

And you can do that. And sometimes that means choosing a very modest lifestyle, so you can afford your lifestyle. I chose that.

I could have gotten a bigger house. I could have gotten a nicer car. I know there were people that gave me a side eye for the older car that I drove.

That's okay. My kids, definitely their friends had way nicer houses. We had lived in a nicer house.

I definitely downgraded. But I did those things so I could afford my lifestyle. I could afford all of it.

I didn't, I wasn't stretched so thin that I had trouble making insomnia.

So I would encourage you, if you are waiting a year before you start dating again, or whatever that is, to take that time to really hone your financial skills and really work on winning with money so that it is not a factor when you start dating.

That you choose who's right for you, who makes your heart melt, who the right person, and that you're not choosing somebody because you really need help, okay? Hear me on this and make financial discipline a priority. It matters.

So, like I said, four things. Slight recap, am I ready to date? Number one, has it been enough time?

Number two, have you dealt with the way your last relationship ended? Number three, are you financially sound? And number four, are you happy?

Once again, that sounds kind of odd. But hear me out, I think we've all known somebody, and maybe you have to go back to high school, but we've all known somebody who thought they would be happy if they had a boyfriend.

If I only had a boyfriend, I would be happy. That puts a lot of expectation on the other person, if they are the one that has to make you happy. Now, yes, you get into a relationship, and you are happy, and that's great.

I'm not saying another person can't contribute to your happiness, but they don't need to be the only source of your happiness.

If that's what you're looking for, you might need to take a breather and just try to figure out how to be content in your own life.

Now, I will say that when you're going through a difficult season, and it feels like you're starting over, you're not going to be happy like schoolgirl giggly happy, okay? I mean, that's not realistic, and I get that. But can you be content?

Can you be at peace with where you are in life? And if the only reason why you're dating is because you think that will make you happy, that might be a red flag that you're not ready yet. So happiness comes in a lot of different varieties.

So when I say, are you happy, maybe not, like I said, giggly schoolgirl, but are you at peace, are you content? Are you okay with where you are?

So I was at peace, I was content, I was okay with where I was, I was able to laugh again, I was able to find joy in little things. Yes, I met my husband. Yes, we got married.

And yes, I am so much happier now than I was back then. But I wasn't looking to date to find happiness. That wasn't my thing.

I was at peace with where I was. But yes, I am way happier now, 110%. It's true.

I think the thing is, are you looking for someone to make you happy? Or can you be content and at peace with your life the way it is? And just be honest with yourself.

It's okay. I wanted companionship. I did want to find somebody to share my life with.

That was important to me. But I wanted to be in the right headspace when I did it. And I didn't want to be needy, and I didn't want to be still dealing with stuff from my past, taking the time to make sure that, you know what, I really am at peace.

I really am okay with where my life is. Yes, it's drastically different than what I thought it would be. Yes, this isn't what I envisioned.

But you know what? I'm okay with that. I'm happy with this life.

That's the place I was at when I started dating, if that makes sense. So I wasn't looking for somebody else to make me happy. That wasn't my goal when I was dating.

My goal was to find companionship. I wanted to share my life with somebody. So ask yourself that, and just be real.

Am I looking for somebody to make me happy? And that's a toughie. I mean, it's hard, we can lie to ourselves a lot.

But try to the best of your ability to be honest. What are you looking for in dating somebody? And we look for all kinds of different things, and that's okay.

But happiness is an inside job, okay? And if you're expecting somebody else to make you happy, at some point, that's gonna break down. They're gonna do something that hurts your feelings, something's gonna go wrong.

And then what kind of relationship do you have if they no longer make you happy? So let's not put all that weight on another person. Now, when you do find the right relationship, yes, it does make you happy, and that does happen.

But maybe let's not let that be the reason we're looking, if that makes sense. That, I guess, is what I'm saying. So those are the four things to maybe ask yourself that I would recommend.

Are you ready to start dating again? You were in a long-term relationship. That relationship ended.

Are you ready to start dating again? What would that even look like? Well, the four questions you ask yourself, has it been enough time?

And that rule is, according to experts, not me, but I think it makes sense, is wait one month for every year you are in a relationship. The second question is, have you come to terms with the way your last relationship ended? Are you okay with that?

Have you dealt with that? Number two, are you financially stable? And number three, are you happy?

I think if you can answer these questions and you work through them honestly and openly in your own head, and maybe with a trusted family member, a friend, or a counselor, you'll have a better idea of whether or not you're ready to start dating.

You'll have a better idea of where you are in this healing process. And you can come back to these questions in six months, and you might have different answers, because we grow and we change, and as we heal, our answers change, okay?

But this might just give you a gauge of where you are. I would be really interested to know what you think. What do you think is a good gauge of whether or not you're ready to start dating?

What would you say that I left out of my list? I would love, love, love to hear from you. You can find me online, www.workingonamazing.com.

I'm on most social medias, but I do hang out on Facebook the most, just working on Amazing. You can find me there, drop me a line. Let me know what you think is a good gauge of when you're ready to start dating.

Maybe it's something different, maybe it's something quirky or funny. I would love to hear it. Please, please reach out and let me know.

Thank you for joining me today. I look forward to talking to you next time. Bye.