Tired In My Twenties

Dating after a long-term relationship

July 29, 2022 Melissa Lent Season 1 Episode 2
Dating after a long-term relationship
Tired In My Twenties
More Info
Tired In My Twenties
Dating after a long-term relationship
Jul 29, 2022 Season 1 Episode 2
Melissa Lent

How do you start dating again after a long-term relationship? 

In this episode, we’ll hear from my friend Rebecca Alisandratos on when and how she made the decision to start dating again after a long-term relationship, and how her process was more about building her confidence and focusing on herself more than anything. She’ll also share her online dating experiences, how she connected with others after her relationship, and what dating culture and online dating is like in your twenties. 

Full transcript and show notes at tiredtwentiespod.com.

In this episode, we cover:

  • Finding closure after a long-term relationship
  • Building confidence in yourself and your identity
  • How it feels to connect to other people after leaving something long-term
  • What dating culture and online dating is like in your 20s

Show notes:

More about Rebecca Alisandratos:

Hello! I'm Rebecca, I'm 23 and I'm a marine mammal trainer. I'm just starting to figure out my adult life and am learning new things about myself and the world along the way. 

Instagram: tiny_rebeccersss

Show Notes Transcript Chapter Markers

How do you start dating again after a long-term relationship? 

In this episode, we’ll hear from my friend Rebecca Alisandratos on when and how she made the decision to start dating again after a long-term relationship, and how her process was more about building her confidence and focusing on herself more than anything. She’ll also share her online dating experiences, how she connected with others after her relationship, and what dating culture and online dating is like in your twenties. 

Full transcript and show notes at tiredtwentiespod.com.

In this episode, we cover:

  • Finding closure after a long-term relationship
  • Building confidence in yourself and your identity
  • How it feels to connect to other people after leaving something long-term
  • What dating culture and online dating is like in your 20s

Show notes:

More about Rebecca Alisandratos:

Hello! I'm Rebecca, I'm 23 and I'm a marine mammal trainer. I'm just starting to figure out my adult life and am learning new things about myself and the world along the way. 

Instagram: tiny_rebeccersss

Melissa: So you’ve been in a relationship for years and then—you’re not. You’ve broken up with your significant other and now you’re out in the dating wilderness. And you’ve made it to a point where you think it might be time to get out and date again. You’re scared, but you’re also excited. 

But—how do you do it? You’re thinking to yourself, “My game has dried up. I can’t do this again.”

Let me tell you, you can. 

While dating in your 20s can seem potentially limitless, especially with dating apps, our guest today, my good friend Rebecca Alisandratos, is going to tell you exactly how she got back into the dating game after being in one long-term relationship her entire college career. And most importantly, how finding the strength to put herself out there had to start first with the confidence and peace she felt within herself. 

She will tell you when she knew she was ready to start dating again, how she did it, her juicy dating experiences on Hinge and Bumble, and how it felt to open up to new people after having been with one person for a really long time. And hopefully that can help you on your own journey to jumpstart your dating life again. 

Let’s get into it. 

[Intro music]

This is Tired In My Twenties, a podcast about figuring out adulthood one episode at a time. I’m your host, Melissa Lent.

Melissa: So I'm here with my friend, Rebecca Alisandratos, who I've known since college.

She currently lives in Miami, but she grew up in New York City, just like me. She is an apprentice marine mammal trainer at Miami Seaquarium, working with seals and sea lions, one of the coolest jobs in the world, in my opinion. And today, we're not here to talk about Rebecca's relationship with aquatic animals, but we are here to talk about her dating after her long-term relationship. Rebecca, thank you so much for being here. 

Rebecca: Thank you for having me. I’m so excited.

Melissa: I'm excited too. I'm excited you're here. So to talk about your dating life after your relationship, we have to talk a little bit about that long-term relationship that ended.

When was your last long-term relationship and how long did that relationship last?

Rebecca: I've only had that one long-term relationship and it was all throughout my four years of college. So when I first started college in 2016, until it ended in summer of 2020.

Melissa: Hey there, this is Melissa from the future. I wanted to drop in a little extra context of Rebecca’s long-term relationship so you can understand why it was such a huge mental shift for her to even think about dating afterwards. Also, we won’t name her ex for privacy reasons; but I spoke to him to get his take on this episode.

Rebecca and her ex got together at the beginning of an incredibly formative period of their lives: the start of college. 

Just a few months in, they were together. And by the nature of living in the same place and going to the same school, they spent a lot of time together. Rebecca said they probably spent 80 percent of their time together.

They would hang out on the Sky Bridge of our college in between classes doing work or having lunch together. If they ended class at the same time, they’d take the subway home together. If not, they’d meet up later to hang out or do homework together. Rebecca said it was almost like they were living together.

For her, those four years were marked by milestones with each other. It was Rebecca's first date; her first kiss; her first time meeting a partner’s parents; her first time going away on a trip abroad with a significant other.

And it ran in tandem with their college career, this influential time in their young adulthood where they developed their professional interests, formed lasting friendships, and planned their next steps.

But maybe because of how used to they were of always being with each other, when it came time to plan their next steps, they weren’t sure how they fit into each other’s lives anymore. 

Let’s go back to the interview. 

Melissa: Yeah. And that was a really long relationship. How did you know it was time to leave that relationship?

Rebecca: We were at this point where it was a big transition point. We had graduated and we had to have a discussion of where our lives were going.

I wanted to leave New York for the purpose of my career. And he wasn't done with what he wanted to do in New York and will probably stay in New York for the rest of his life. So it was a location-based thing that made us end our relationship.

So although we had been dating for four years, we didn't think that we would do well with long distance. And that was from previous experiences like during summers where we would be apart. And it would just be the hardest part of our relationship.

So we came to a mutual decision that breaking up was probably the best thing for us to do.

But we are still part of the same friend group. 

Melissa: Honestly, everyone, this was probably the most amicable breakup I've ever witnessed. 

Rebecca and her ex are both my good friends and I have not seen a relationship that ended more peacefully.

Rebecca: It wasn’t easy by any means, and there was also a lot of background.

Melissa: Yeah, no, definitely. At least what I saw was pretty amicable and I hope that you still feel that it was amicable.

Rebecca: Yeah, definitely.

Melissa: Hey, Melissa from the future again. You’re probably wondering: how the heck did they do that? How do you break up with your ex and still stay cool with them? How does that work?

I went back to Rebecca after our interview to get some of those details. And it seems the most important thing was leaning on their mutual respect for each other to have things end peacefully. She said because they knew months before they graduated that she wanted to leave New York eventually and he wanted to stay, they had first silently come to the conclusion they’d have to break up. 

They delayed the decision as long as possible–right before Rebecca moved across the country to San Diego for an internship. She told me that there were a lot of conversations going over every scenario of them staying together vs. breaking up, weighing the pros and cons before coming to an agreed decision. It was time to break up. 

And then after they agreed to split, they communicated openly about what came after.

First, how they would handle having less communication with each other, since they were used to talking every single day. As she drove from New York City to San Diego with her mom, Rebecca says at the outset, they continued texting all of the time. But it would dwindle eventually. Until they barely texted at all. 

They also spoke about how they would break it to their friend group, which included me. But they knew because Rebecca was leaving,  there wasn’t going to be a big discussion of who hangs out with us when, because our other friends and I would barely get to see her. 

There was no big fight that drove them apart. It was circumstances that they couldn’t reconcile. It was Rebecca’s first long-term relationship, and her first breakup.

But more than a year later, Rebecca started to look to the future.

Let’s get back to the interview. 

Rebecca: I didn't start dating again until fall of 2021. So we had broken up in summer of 2020, and I had this whole year of moving around and figuring out my career. And then I finally land this pretty solid job out in Miami.

So once I knew that I had this stable position and was starting my life out here, I was ready to put myself out there again and start dating. I had gotten complete closure from my past long-term relationship and I was really missing being in a relationship.

So I just decided to see what dating would be like.

Melissa: Woo, we love a stable job, stable salary with benefits.

Rebecca: [laughing] Wooo!

Melissa: [laughing] Wooo!

Melissa: You said it really took you a year to try to find this closure. For you, what does closure mean?

Rebecca: That's tricky. I think it just means fully coming to terms with being okay by myself.

After the breakup, initially I was missing him a lot and it was just like this big change. And I knew that I wouldn't be ready to date anybody else because my heart didn't feel fully healed.

 I guess closure means to me, just feeling confident in myself as an individual and feeling like, although I still have love and care for this person, it has evolved in something that is completely different to the love and care that I had while in the relationship. It's just that shift in like the mentality and the type of relationship that we have, and then having had all that time to myself to be alone and to feel like I was ready again, to find something different and new.

Melissa: No, I like that. I like how you said that there’s still love and care there, but the way that love and care can manifest over time can be entirely different. What you feel for somebody, it can change, and that doesn't necessarily make it better or worse than it was before, but it's just different.

Melissa: During that interview I had with Rebecca, I realized that her biggest shift towards starting to date again was not with the change that happened with her ex, but the changes that happened within herself.

When they broke up, Rebecca had moved cross-country to San Diego for an internship. And there, she had to contend with so many major changes to her life; her previous relationship was just part of that. She had to live on her own. She had to make friends. She had to work and figure out her career.

Instead of dating, Rebecca decided to work on her friendships. Alone in a new city, Rebecca downloaded Bumble. Bumble BFF, for friends! There she matched with a bunch of people to hang out with.

She also worked on her relationship to herself, going out alone and enjoying her own company.

She made major decisions about her career in marine biology. She had been applying to grad school, but realized research wasn’t for her, and she wanted to pursue training animals instead. She dropped her grad apps and started looking for training opportunities.

That’s where it got a little weird. She got another internship–but back in New York City in its aquarium. She felt nervous about seeing her ex again. But she decided to focus on her career, her family, and also–her hobby. She opened an Etsy shop to sell her crochet crafts. I bought two solid winter beanies from her. 

And then finally, the summer between her working in New York’s aquarium and her landing her job in Miami aquarium, she went to visit her family in Kefalonia Greece with a friend. According to Rebecca, she was having her Mamma Mia, hot girl summer! And she was scoping out hot guys with her friend–respectfully, because it was still a family vacation. 

And being interested in anyone again, even if it was just a passing glance, helped solidify Rebecca’s closure. 

Once she got to Miami to work at the aquarium, she was ready to start dating again.

Okay, back to the interview. 

Melissa: Also you were living in Miami, you wanted to get on that Miami dating scene with those Miami boys, ayyyy. 

Rebecca: [laughing] Oh, boy.

Melissa: So let's talk about that. How did you do it? Did you use dating apps? How are you meeting these people?

Rebecca: I first started out by just downloading Hinge and I was solely on that dating app for a while.

Then it eventually evolved into both Hinge and Bumble. And it was just all through online dating. 

I'm not the type of person to go out and just talk to random people. And since it was such a big move and like I was new here, it was just easier to meet people in an online environment.

Melissa: How long did it take you to find other people to date?

Rebecca: I had a lot of conversations with people. A lot of them would fizzle out really quickly, but I think when I first downloaded Hinge, it was like late October, mid-October, something like that. And I ended up going on my first date in early November.

Melissa: [laughing] Dang a couple of weeks, they’re trying to scoop you up.

Rebecca: [laughing] Oh yeah. Hot commodity over here. But that was the first person that I dated through the dating app, which was also an interesting experience if we want to get into that.

Melissa: Oh yes. Let's get into it. 

Rebecca: [laughing] Okay.

Melissa: You just said it was interesting. I want to know why.

Rebecca: It seemed really fast because this is the first Hinge dating experience that I had and I don't know if I would call it a full on relationship or if it was a one month dating period. But it progressed really fast, and I'm not entirely sure why, but we were both comfortable with how it was progressing until it got to the one month point. And I realized that I had thought it was progressing much faster than he did.

And I got dumped out of the blue, which was very, very confusing to me. And having that be my first online dating experience could have probably completely negatively affected my outlook on online dating, but it didn't. After a lot of reassurance from people and some reflection, it only took me 24 hours to fully get over this man [laughing] who had just dumped me out of the blue.

A couple of weeks later, I was like, yeah! Maybe it was out of boredom. Maybe it was because I was missing a relationship, but we were back on the apps.

Melissa: Yeah, no, I actually do remember that because you were updating us and telling us what was going on. And I was like, dang, I thought it was going so well, there was zero signs that that was not going well.

Rebecca: [laughing] Zero signs, I felt so blindsided, but that's okay.

Melissa: It's fine. You're honestly better off. And you took 24 hours to get over that guy. Psych, miss me with that. Rebecca’s a savage. She doesn't care. [laughing] You were saying that a lot of conversations that you had sometimes would fizzle out.

Rebecca: Right.

Melissa: You had this dating period that was a month long, and then that fizzled out. How do you stay motivated or not have your energy go down after some of these conversations?

Rebecca: It's cause I take breaks. Sometimes I get into moods where I just want to swipe and just go through people and see if I find anyone I like, send messages and then like we're talking and things like that.

But then there are other days where I forget about dating apps and focus on myself, especially if there's a lot going on in life at work or socially with my friends and things like that. So it's not having these dating apps be my sole purpose. Otherwise it would get probably very draining and boring fast.

Melissa: That's great. You live a full life. You have your work, you have your friends, you have your family. Dating is only one part of your life. Also, let's be real here, right? 

Everyone. Rebecca is a catch, okay? You can't see her because this is audio, but she's a catch. You're gorgeous. You're a sea lion trainer. You're a trapeze artist. You're a great crocheter, “Boy, I will make you a blanket so we can cuddle in it” kind of girl. 

Rebecca: [laughing] Melissa’s flirting with me!

Melissa: Actually, I feel like I'm your matchmaker, right now. [laughing] But seriously, it's a no brainer to swipe on Rebecca.

Rebecca: Wow, thank you for the confidence boost.[laughing] I really needed that today.

Melissa: No worries. I'm always here for that. Let's get into some of those juicy details, right? What were some of the top dates you've been on versus some of the–not top dates. I don't want to say bottom dates, but [laughing] that's kinda what it is. I am curious what kind of experiences you've had.

Rebecca: A majority of the dates were obviously going out for food and just talking and things like that. I've had a couple of dates where it was a lot of walking and talking.

There was one date that I feel like is pretty unique just because I feel like a lot of people wouldn't do this, but we just hung out and played board games and built Legos which is a really interesting kind of date to have. It just showed that both of our personalities were comfortable with something like that. And there was also a basketball game. That was really cool, to go to a professional sporting event, which I hadn't gone to previously.

Melissa: Those are some fun dates. Were there any dates where you're like, it's kinda not great?

Rebecca: Only one date and it was the one that] I only went on the first date with this guy and then it ended after that. We just went for drinks, but the conversation and the physical attraction just wasn't there. So that's why that one ended pretty fast.

Melissa: I went back to Rebecca after this conversation to ask what separated her good dates from the bad dates. She told me that the good dates were where she was able to connect the most–they would get deeper than the superficial and talk about things that mattered to them, or stories they wouldn’t just tell any stranger. Basically being able to have an easy-flowing conversation where you know both people’s barriers are down. On one date she really enjoyed, the guy told her the entire plot of a movie starring a walrus. And that honestly screams, “I am comfortable around you.”

But on the date Rebecca just described that was a dud, the guy wasn’t the same in person as he had been on the app. Through text, she had learned about his personality, about his family. In person, it was awkward. There were long stretches of silence. There was no flow. And the conversation stuck to surface level, mostly icebreaker questions rather than anything deeper than that.

And that was not it. Okay, back to the interview.

Melissa: How did it even feel for you to date after a long-term relationship? You'd been with someone for four years, which is a really long time. And then to go and try to talk to other people and connect to other people.  How did that feel?

Rebecca: Very weird. [laughing] I also think it was just extra strange for me because I had never done the whole dating thing before this long-term relationship either.

I don't know if it was comparing or if it was like things would happen when I would be meeting these new people that would just remind me of my old relationship— like topics that we had in common, jokes that would come up that I would remember as also being jokes I had in common with the other person.

Some people have a type. So then I was thinking, “Oh my gosh, it's just happening all over again. Maybe I do have a type.”

I think how I got out of that is just then focusing on the things that I have in common with these people that I might not have had in common with my ex and then thinking like, “Oh, that's a fun, new thing that I have in common and that I appreciate, and is why now I'm like happy to see this person” or something like that, or like excited to see if a relationship can start with this person, because it's just something that I realized that, oh, might have been missing from that previous relationship. So it’s just something new.

Melissa:  It feels you were still trying to detach yourself a little from your previous relationship, but once you were able to do that, you were able to see the unique qualities that the new people that you were dating had.

It's also your chance to do this kind of exploration, which is what you're doing of, “Is there someone else that I can connect with in this way like I did maybe in my previous relationship?”

Rebecca: And I also feel like I’ve just grown as a person. If I had tried dating a while ago before this long-term relationship, I probably would've been way more shy and awkward than I am at this point in my life. So because of that change within myself,  I have gotten to a deeper level with most of these people that I've had conversations with on Hinge and Bumble. And that's actually why I've ended up going on dates with them is because we were able to break any surface level conversations.

Melissa:  We love a confident and open queen, yes! [laughing]

Rebecca: [laughing] We’re trying, we’re trying.

Melissa: How have you felt that your expectations or goals for a relationship changed if, if they did?

Rebecca: I guess because dating is so new to me now, especially because my last relationship was the long-term one, it was also my first relationship. So now I'm just more open to figuring out what this person is like and becoming their friend first and understanding them before I am even thinking about, “Oh, I want this person to be my boyfriend.”

It's more of a slow burn now is all that I expect from these dates, because the first date could go terribly. So it's just like getting to meet this person, seeing what they're like, and then seeing where things go from there, but not trying to set any high expectations in case things do come crumbling down.

Melissa: Was that a change from say your long-term relationship?

Rebecca: When I went into that long-term relationship, I wasn't necessarily hunting for a person to date and it just happened.

And we were friends first. So it's very different from meeting a complete stranger, trying to become their friend, and then trying to become more than that. 

Melissa: Yeah, definitely. You were saying that you weren't really looking for a relationship at that time. Now you're in the dating scene, you're going on a bunch of dates and things like that. And I feel like in your twenties, maybe that's expected.  

Rebecca: Definitely as you get closer to your late twenties even, is when people start to feel like time is running out and they are expected to date. But also in this day and age, I feel like there's a lot of people out there who are perfectly comfortable on their own, and they know that from like the get-go from their early twenties, they're just like, “I'm focused on myself and I don't really want to be looking for anybody.”

I definitely think there is still some of that mindset where people are expected to be dating and to find people at this point in their lives. But I do think it's still more of an old mindset and it is changing at this point as we are progressing. 

And I just think dating in your twenties at this day and age is also just very hard because especially with COVID having happened and then online dating became a really big thing because of that.

It's hard to go out and just say hi to a stranger or have a meet cute, like they do in movies. And we are very dependent on technology. So it just feels like the most natural thing now, even though technology itself is pretty unnatural. 

Melissa: Yeah, those are great points. Well, this is a question that I actually ask all of my guests. What did you think adulthood would be like? And what is it for you now in reality?

Rebecca: So I feel like growing up, I don't know if I ever really thought in detail about what adulthood would be like, I would think of it as like the stereotypes of having a job and eventually finding the person that you love and building a family and all that kind of stuff.

Once I was getting to the point of approaching adulthood, I would think about more of the nitty gritty of what it was going to be like and realized that it was going to be very hard to make that transition. And that still proves to be correct, because there's just a whole lot in terms of like finances and your job and stability and relationships and everything like that, that proves to be pretty difficult. But it's also fun and exciting.

It's just a happy medium between chaos and excitement. [laughing] That is what adult life is like currently.

Melissa: I do feel like that. This is great, Rebecca. I also wanted to ask where can people find you?

Rebecca: If people want to follow me on Instagram, I do have a personal Instagram.

It is tiny_rebeccersss. 

Melissa: Well, Rebecca, thank you so much for joining me today and being so open about your experience. It was really nice to have you. 

Rebecca: Thank you. I had so much fun.

Melissa: By the time you hear this episode, Rebecca will have started dating someone new—for the long-term. 

Their first date was spontaneous. They’d been talking for a week before he had to leave town for a little while. But right before he left, he said he’d regret it if they didn’t go out together.

On their first date, they cut past the superficial and talked about things that mattered to them. About the meaning of their tattoos, about how important family was to them. Rebecca instantly felt comfortable with him, and liked how keen he was on getting to know who she was. 

She paused her dating profiles so she wouldn’t match with anyone else. 

And after their second date, they both decided to delete their dating apps altogether. 

Starting to date after you’ve gotten out of a years-long relationship can be incredibly scary and daunting. How do I connect with someone new and open up to them, especially in the world of online dating? How do I flirt? Do I even know how to do that anymore?

But it can also be fresh and exciting. It can mean finding someone you have a connection with that may be stronger than the one you had previously. It can also mean finding self-confidence to put yourself out there again. 

I hope you give yourself permission to one, not feel like you have to date and two, if you want to, to be open and see where it takes you. Dating culture in your 20s is a vast expanse of opportunity, possibility, and Hinge matches—but you are allowed to go at your own pace, and break any cultural norms that say otherwise. Whether you just got out of a long term relationship or you’ve been single for a long time— don’t feel like you have to succumb to the wills of dating culture. Just do you! 

Rebecca took her time before she started dating—more than a year. And she used that time to figure out more of what she wanted for herself, outside of her romantic relationships: her professional interests, her friendships, her hobbies. She’s a crochet queen! And once she felt settled, she made the decision to date again. You can take the time to figure out who you are and who you want to be too. 

She doesn’t know what will happen with her dating life, and neither do you. But you don’t have to. We can’t plan for everything but we can accept and embrace what life gives us along the way. 

[Outro music]


Melissa: Tired In My Twenties is an independent podcast produced, edited, and hosted by me, Melissa Lent! Get detailed show notes at tiredtwentiespod.com and subscribe to my newsletter at tiredtwenties.substack.com. 

Music and sound effects for this episode come from Artlist. Special thanks to Laura and Nate Davis, Isabel Gouse, Nicholas Lume, Winnie Shi, and Sarai Waters.

Thank you for listening to Tired in My Twenties, and join us next time to keep figuring it out together. 

And now, if you’ve listened this far, here’s an outtake: 

Rebecca: So when I first started college in 2016…Right? Yes.

Melissa: [laughing] Are you sure?

Rebecca: [laughing] Yeah, it's been a while!

Melissa: I have to remind myself every day, what day it is, what week it is, what year it is.

Sometimes I still write 2021, sometimes I'm like, yeah, last year when I graduated college, when that was two years ago!

Rebecca: [laughing] Oh my goodness!

Melissa:  I know we're old. We're so old. 

Rebecca: Time flies. Jesus. [laughs]

The long-term relationship
Breaking up amicably
Finding closure
Online dating
Finding connection after a long-term relationship
Personal growth and relationship expectations
Dating culture in your 20s
Reflections on adulthood