How to Date Your Friend’s Former Flame Without the Drama

Words by Natelegé Whaley. Illustration by Sam Liacos.

“Messy” — One of the responses we received when we first put out a call for submissions to this dating question prompt. These situations can be. We’ve seen how they play out on television shows like This Is Us, where leading character Rebecca is married to her late husband’s friend Miguel. Or on Queen Sugar, where Remy briefly dates Nova after having an intense romance with her sister Charley. 

But fiction borrows from reality. As taboo as dating a former flame of a friend or family member can be, it isn’t that uncommon. Depending on the circumstances, some may see it as backstabbing or a dealbreaker for a friendship. While for others, the honesty that’s required to have conversations in these awkward situations surprisingly strengthened their friendship. ILY got six people to candidly share their experiences, and you may be surprised to learn the outcomes.


She’s dating her cousin’s Bumble match but taking her time with it…

“I’ve always maintained that I’d never date someone a friend dated, had sex with, or even kissed. But here I am, eating my words. My cousin, who also happens to be one of my best friends, used to date this guy I’ve been seeing. She met him through Bumble about two years ago and to be honest, he annoyed the hell out of her. She introduced us and while he annoys the hell out of me too, I still like him. 

She joked that I should date him. They’d only kissed, so it’s not that bad, right? She now laughs at the fact that we’re dating. We’ve only been seeing each other for a few months. I’m trying to take things slow. I had to press him to slow down. If he had it his way we’d probably be coupled up by now, but I’m extremely non-committal. We’re all from the same country and there’s a kind of history, upbringing that I guess we instinctively look for in a partner. He’s definitely good on paper, but the jury’s still out on real life.” —  Talisa S., 29


She ended up bonding with a friend over their shared ex-boyfriend…

“My best friend, Tara, dated this boy throughout high school. (They broke up right before we started dating). We all went to the same high school, I was acquainted with both of them, but not close friends. It was not until after I was trying to leave the toxic relationship with the boy that Tara and I became close. Tara and I were introduced by a mutual friend and began bonding over similar experiences that we had with this boy. He was emotionally abusive and manipulative and Tara and I would talk about our experiences and she would explain how she healed from them. 

Now neither of us talk to the boy, but are best friends and continue to help each other heal and grow.

Shayla C.

Tara genuinely cared to guide my healing and help me leave the situation. She always gave me the room to share my experiences with her, even when I continued to pursue the toxic relationship. She never told me what decisions to make or how. I think I had reservations about being introduced to Tara at first because I dated her ex a few months after her, so I was vulnerable and scared that Tara wasn’t going to be interested in my friendship because of us sharing an ex-boyfriend. This ended up being the opposite of what happened. I ended up cutting off all communication with this boy because of the strength that Tara helped me to find, which also strengthened our friendship. Now neither of us talk to the boy, but are best friends and continue to help each other heal and grow. A true testament to the power of women supporting women.” — Shayla C., 22


He dated his friend’s ex, but then things got messy…

“Well, this was in my college years. Two of my friends were dating. They broke up. A couple years after that, my homegirl and I started dating. Everything was smooth at first. I spoke to my homie about it before I made any moves. He was actually happy for the both of us so I proceeded to make a move. Everything was good. We dated for a year or two before we called it quits. We’d still deal with each other a lot. 

Come to find out in the midst of the breakup, she was messing around with the friend she broke up with. I saw them together at his house. We stopped speaking for a long time. Eventually, we spoke and he told me she told him we broke up way before we did. Showed me messages and all that. Me and him are cool again though. She had a kid and got married. I hope everyone is doing well.” —  Dom O Briggs, 28


She secretly wanted her friend’s former fling and finally went for it…

“My friend liked this guy named Bobby, but their connection didn’t go anywhere. I knew they had gone to school together. Me and Bobby had also gone to the same school at one point and were friends on Facebook. So when my friend had a get together for her 30th birthday, I saw Bobby. So I said “Hi. I’m Lisa. How are you?” And he was like, “Hi.” He gave me a hug and and at various points in the party, he strikes up a conversation. He was showing that he was interested. But I knew my friend and him had some sexual dealings. So I kept avoiding him. 

The night comes to a close and he says to me, ‘Hey, I’m trying to date you. I’m trying to court you. Let me have your number.’ I was so in shock. I was like, ‘Didn’t you fuck with my friend? I can’t really do that.’ My friend noticed the exchange between he and I and called me later that week and said, ‘I notice you were talking to Bobby. You both might be soulmates. You never know what can happen. It just didn’t work out between he and I.’ Again I refused because they both were previously involved sexually.

So time goes by and whenever I would talk about the kind of guy I would like, she would always bring up Bobby’s name. And I would say, why the fuck is she doing this? Meanwhile Bobby is reaching out to me on the side and I’m ignoring him. But I’m actually interested in Bobby. So one day I initiated a lunch date with my friend and said, ‘What’s the deal? Would you have an issue?’ She said, ‘I would not mind. He and I are not compatible and you two may be compatible so I don’t want to interfere.’ 

I took that as a green light. I reached out to him and so we hung out a few time, but nothing serious ever came from it. I don’t talk to him anymore. Her and I are still friends and we have no issues and we laugh about it now.” — Lisa B., 37


She became best friends with the woman her ex-boyfriend dated after her…

“I started dating this guy in high school. He was my first boyfriend and first love. We were involved for a little over three years. We dated into young adulthood, but he cheated on me a few times and became emotionally manipulative. Towards the end of our relationship, he moved to a different city and we attempted long distance love. But he began hanging out with a girl named Shayla from our hometown and after we broke up, they got together. I didn’t know her very well but we had mutual friends so it was a little weird at first. But I wasn’t bothered by her. 

After a year or so I ended up moving to the same city as them for the remainder of my college years. My best friend who I moved with was really close with Shayla. So we began to all hang out with each other, minus my ex. At this time Shayla and him were broken up or on rocky terms, and so there wasn’t any conflict. But Shayla was very hesitant to interact with me because of my past with him. Shayla and I began to notice we had a lot in common and we weren’t each other’s enemy. We nervously suggested going to a concert together alone and after that we became inseparable. 

We both learned how much we connected and realized that going through what we did with this stupid guy helped us understand each other in ways a lot of friends may not.”

Tara B., 22

We went to school together and found out we had so much in common that a guy could never keep us apart. She eventually ended things with him and we were able to talk through a lot of the same problems that we both faced dating him. Even to this day we laugh at our experiences. We both learned how much we connected and realized that going through what we did with this stupid guy helped us understand each other in ways a lot of friends may not.” —  Tara B., 22


He found out in the most awkward way that he and his friend were dating the same man at the same time…

“I once went to a friend’s game night when I met a guy that I thought was really cute! I assumed he was invited by my friend, as a friend, never knowing that they were currently dating! I flirted a bit and got his number. About a week later, he and I went on a date. The date went great, but during, he informed me that he was also dating other people. I made no big fuss. At any moment we’re all swiping for the next. He told me that he was going on an indoor rock climbing date with someone else, the weekend after our date. I made no big deal about it and we agreed to see each other again. 

How the hell is he planning on dating both of us at the same time?

George C., 29

The weekend comes up and I notice that my friend who invited me to the party was also rock climbing. I thought nothing of it, until I did. I was like ‘Nooo way!’ He would tell me if he was dating my whole friend. I sent out the bat signal to my BFFs whose investigation skills are FBI worthy. In about 20 minutes they found my date’s Instagram and clicked on his stories. In the last story I saw a quick shot of my friend.

I’m like, How the hell is he planning on dating both of us at the same time? He and I go on another date and I make a joke about him dating my friend. He was completely red. He laughed and said, ‘I definitely wanted to tell you before you found out.’ I’m like, ‘How are you trying to date the both of us? Not only are we complete opposites, but we’re friends!’ And he was like, ‘Well, I mean, I started talking to him first but it never bubbled up into anything until after I met you and already agreed to go out.’ We talked a lot about the differences between my friend and I but I played passive about it as to not sound immature.

I told him it didn’t bother me, but to let me know if he started feeling him more than me and I’ll fall back. We’re still dating so I don’t have any conclusions for you. I have since been to more game nights and outings with my friend but we actually never talked about it! And needless to say my date hasn’t been to any of those game nights since!” — George C., 29