I'm Dating My Ex--Four Women Tell All

October 17, 2014 by Claudia Saide
shefinds | Style

Have you ever thought about ‘the one that got away’—that guy or girl from your past that still makes the occasional cameo in your dreams, or that gives you a little tinge of regret when you see stories about them on your Facebook feed? That relationship that was so good it’s almost hard to remember why you broke up (oh, right… all those fights). Sure you have. We all have.

Thinking about life’s What Ifs is normal, and that includes thinking about whether you and your ex were really meant to be. Certainly, sometimes when it’s over, it’s just over, but some relationships do deserve a second chance.

There are many pros and cons when considering whether or not to date an ex, and we wanted to know all of them. We sat down with 4 women who’ve done just that–all with the different outcomes (one even married her ex!) If you’re entertaining the idea of getting back together with an ex, you need to read this:

The Women: 

Ashley*, a student at Hunter College in NYC, and her ex decided to get back together after being broken up for two months. The second time was completely different from the first—they went from living together, to having a long-distance relationship where they never actually saw one another in person. After a few months, she realized that it just wasn’t going to work, for many other reasons than just being so far apart. To date, they are no longer together.

Leslie*, an editor in New York, gave the relationship with her college sweetheart a second chance after being apart for six years. She’d just ended a really bad relationship and was looking for the security of being with someone she knew she could trust and feel secure with. They’ve been together for almost four years, and are still going strong.

Gabby*, a blogger, and her ex gave it a second chance after their first sudden break-up. They ran into one another at a party, and after a few drinks, they were boyfriend and girlfriend again. The second time around didn’t last long at all, and they are no longer together.

New York-based electrologist Keren and her ex got back together after running into one another in Europe. They’d only dated a couple of months the first time, and they ended it because he wasn’t ready to commit. But after seeing each other again, they quickly started to date, and eventually got engaged. They’ve been married for over a year.

SHEfinds: How did things start up again?

Ashley: “When we originally broke up, we stayed in touch, so it led to emotional confusion.” (The two broke up because Ashley moved to another country, not because they didn’t want to be together.) “It was out of our control, so there were no hard feelings, and that ‘let’s be friends’ line blurred really quickly.” They kept in touch and talked on the phone often. “We knew we still wanted to be with each other, and little by little we came to a mutual understanding that we were once again exclusive.”

Leslie: “I Facebook’d him! I invited him to dinner, we kept talking after that and boom—we were together again.“ And although things went really well, Leslie left the ball in her man’s court at first. “Since I was the one who broke up with him the first time, I felt like it was up to him to forgive me and give us another try. We dated for a month before officially becoming boyfriend and girlfriend.”

Keren: “We were dating for about two months before we broke up, but then we ran into each other on a trip to Prague, and we just started talking again. Then we got back to New York, and continued to see one another, and eventually got engaged!”

Gabby: “I saw him at a party and I was playing hard to get. He approached me and I basically ignored him. Then he grabbed me and asked me to take a walk, which eventually turned into a drunken fight, which led to a make-up, which led us to getting back together. Looking back, it was all so immature, I had to have realized that it was never going to work.”

SF: What was that first hook-up like?

Keren: “It was so awkward and unexpected, and I was trying to hold out for at least a month into dating again. I wanted to see if he was serious about us this time. But that didn’t really work out, we were dancing and drinking at a club, and it just happened.”

Leslie: “It was just like old times! It actually wasn’t awkward at all. I have always been comfortable with him, even after we kept in touch after the breakup. Part of the reason I am back with him is because he gets me and I can be who I am. Therefore hooking up is what it’s supposed to be—fun. It’s also better, just not as often since there’s a kid in the picture now.”

Ashley: “There was no sex. We never saw each other.”

SF: How about the fights? Is the first break-up still an awkward subject?

Ashley: The main reason Ashley and her ex ended it the first time was because her family didn’t approve of the relationship. They wanted her to be with someone of the same faith, and closer to home. “We would argue about how I was giving up everything to be with him (my home, my family, my friends), and he really wasn’t offering me the same. And this fight never went away, it’d get worse each time we’d have it.”

Leslie: When Leslie and her ex first got back together, they’d have intense conversations about why they’d split up the first time, and how they knew they could trust one another again. But those conversations are less frequent now that they’ve been back together for nearly four years. “We don’t fight often, we banter more than fight.”

Keren: Keren and her husband laugh about the first breakup, and actually see it as a good thing. “It forced us both to to figure out if we were really meant for each other. It’s a memory whether I like to remember it or not, but it really did make us stronger.”

SF: How’d your friends and family react to you guys getting back together?

Leslie: “Everyone assumed we would get married anyway, so I think the breakup is only really meaningful to him and me. We got along great with each other’s friends and family, so everyone is totally fine with it. I think the assumption when we dated in college was that we would be together forever, so our connection wasn’t that shocking.”

Gabby: “My family knew I wasn’t ending up with him. They didn’t understand why I was even dating him again.”

Keren: “My family loved him from day one. I’ve had so many boyfriends that they hated, so it felt good that they approved of him.”

Ashley: “I think my family is happy that it’s over, to be honest. My friends all think it was a good thing I went through it, because I had been struggling with the temptation of dating outside of my faith and community and country forever. I’d fantasized about running away from when I was a child, and had only done so halfway. If I hadn’t gone through it, I wouldn’t have finally squashed those fantasies.”

SF: Have either of you changed since you were first together? Do people really change?

Leslie: “We have both changed a lot. I am a mom now, so my priorities are totally different than when I was in college. Also, after I broke up with him I got into a really awful relationship that really changed me. Things that were important to me before are less important now. And for him, the breakup really hurt him. Our first time around he was all in—totally unguarded, madly, deeply passionately in love. This time he is more reserved—the pain of the breakup definitely still lingers.”

Gabby: “I don’t think people can change. I think the problem in our relationship was that we both wanted one another to change. Deep down I knew it wasn’t possible for him to change because I myself wasn’t interested in changing. We both had different views on life, values, and religion.”

Ashley: “Because of the sacrifices and hardships I went through, being in a different country and experiencing a different culture, I changed. Being with him made me realize so many things about myself and I think I saw those changes as the relationship was on its last leg. So, I have definitely changed.”

SF: Was it the right decision?

Ashley: When Ashley and her ex got back together, she was in a really shaky mental state, and the thought of having that comfort from her ex again sounded good. She was at a really lonely place in her life, and needed attention from someone. “Getting back with him was like allowing myself that impermanent escape. And at the time I’d felt like I ruined my chances of ever being with anyone else, so I settled back with him. “

Although they are no longer together, she does feel that he was one of her soul mates. “I don’t believe in one true soul mate but I believe that he was one of my soul mates. I believe that our relationship made me grow so much as a person, and showed me so much about myself and about the world. So he was my soul mate, because if he weren’t, he wouldn’t have come into my life.

Leslie sees her relationship as long lasting. “That’s what freaked me out at twenty-one. I didn’t feel ready to be with the person I would be with forever.” And although she senses that he’s the one, she’s in no rush to get married.

Keren: “We’ve been married for over a year, and I couldn’t ask for anyone that would fit more perfectly.”

SF: Now that you know what it’s like, would you recommend dating an ex to others?

Leslie: “Our first relationship was actually really great so it wasn’t a stretch for me to see myself with him again. However if there had been huge fights or infidelity or something major that prompted the breakup, I probably wouldn’t have gotten back together with him.”

Ashley: “Sometimes, circumstances are such that people cannot make it work the first time but it can be amazing the second. I think people should definitely give themselves and the other person a chance to breathe and grow and start again between breaking up. I think, only then, can a person be sure that they are not just settling and falling back into old habits. I think that a person really needs to be honest with his or her self and do a lot of introspection before dating their ex, because they definitely broke up for some reason.”

Gabby: Gabby, on the other hand, thinks it’s a bad move. “I think you’re fooling yourself if you think the second time around could be any better. The problems you had in round one will most likely appear again in round two. Try to remember why you broke up in the first place.”

Keren: “It all depends. I think that if I asked for advice about getting back together with my ex, I would have gotten a lot of nos. I stuck with what I felt in my heart, and I think that’s the best thing you can do.”

*names have been changed


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