Ask Single Dating Diva: Dating Friends Ex

So here’s the dilemma when you get a little bit older, the pool of eligible singles gets smaller, even smaller when you don’t live in a big city. So what do you do when you come across someone your friend dated or had a relationship with or was even married to? It’s a tough call. When is dating friends ex OK and when does it cross the line. Is it ever OK or is it plain disrespectful? I say it depends. You have to assess it on a case by case basis. How so? Well, here’s what I told one reader.

dating-friends-exDear Single Dating Diva,

I recently met a great guy online. We really get along, we can talk for hours on the phone and I feel it’s a good match that I want to explore. The problem is that when I told my friend about him she told me she dated him a couple of years ago and it was a messy breakup and she seemed very uncomfortable with me talking to him. What I’m wondering is if dating friends ex is wrong. Especially considering their messy breakup and her and I are not very close. I do value her and don’t want to lose my friendship, but I also don’t want to miss an opportunity at a potentially great relationship. Any help you can give me would be greatly appreciated.


Friendly Dater

Dating Friends Ex

Dear Friendly Dater,

Thank you for your email and question. That is quite the dilemma, you’re right, but I’m sorry to say there’s no easy answer when it comes to dating friends ex. On the one hand, you want to maintain the friendship that you have and on the other hand you want to give this guy a chance because you see some real potential for a relationship. Although I can’t make that decision for you, I can certainly help in your thought process. Dating friends ex – yay or nay? It depends.

Before you make your decision, I want you to consider the following:

  • Do you have all the information about your friend’s relationship with this guy? How close were they? Were they “in love”? Did he hurt her or disrespect her? Why was the breakup messy? Did he cheat? Was he abusive? It seems that there is a lot more to their story than you know about and I think that you should get all the information before making the decision. It could actually show you a side of him you perhaps didn’t even consider. It doesn’t mean because he was like that with her that he would be like that with you, but it’s something to keep in mind.
  • How valuable is your friendship? You that said you weren’t very close but you wanted to maintain the friendship. Keep in mind that if you do decide to pursue dating friends ex that you might lose the friend. Is that a risk you’re willing to take? You did say that she looked uncomfortable with the whole situation.
  • You met online and don’t even know him for real yet. People show a different side of themselves online. They always show their best selves and talk the talk BUT do you know if he will walk the walk? You’re only seeing what he wants to show you and not experiencing him in real life. While sometimes there isn’t a difference, there usually is. Maybe you won’t even click in person, you don’t know unless you actually meet.

Ask-Single-Dating-DivaMy personal rule of thumb is to never, under any circumstance, enter into any sort of liaison, relationship or otherwise, with anyone my friends have dated or had sex with (even casual). I feel it would be disrespectful to them and I value my friendships much more. Think of it, how many men have come and gone and who’s still there? Your friends. There is no shortage of amazing men out there that haven’t been with your friends. I’m not talking about if they met online, had a first date and never clicked and never saw each other again, I’m talking about if they actually dated, if they actually had sex, then it’s a no go for me even if it’s not recent. I also would hope that my friends would respect this as well and not date those I’ve dated. I have encountered some awkward situations where dating friends ex was on the table but I chose friendship because I’m fiercely loyal to my friends, especially my inner circle. But that’s my approach, it’s not the same for everyone. It really depends on the relationship and the friendship. It’s a case by case basis.

It’s really up to you what you decide, but do please consider the points I listed above before you make your decision. Perhaps even consider discussing it with your friend to see where they stand. Dating friends ex is a slippery slope and you need to make sure to land on your feet.

Hope this helps!

READERS: What advice would you give about dating friends ex? Have you done it? Has it been done to you? 

Your Sister in Dating Bliss,

Single Dating Diva

Copyright Single Dating Diva


  1. I definitely think that it depends on the level of the relationship. A few dates may not be a big deal, but for me, if my friend was intimate with someone I have interested in then I can’t do it. I refuse to bring a woman around my friends regularly knowing that he’s done the horizontal mambo with her. It may not bother either of them, but it would bother me. I understand that just about everyone has a sexual history, but when that timeline crosses into friendship and family then I don’t care how wonderful she appears to be, for me, it’s not an option. However, for this lady, she needs to evaluate what’s best for her and that includes if her friend is truly her friend. If she finds out that the relationship was a short one or not as involved then her “friend” may need to get over it as well.


  2. I grew up in a small town (population >3,000). Because it was so small, you were always dating someone else’s ex. In fact, it was just kind of expected that you were going to date someone else’s ex. Some people were fine by it and some (the immature ones) weren’t. If I ever questioned if it would damage a friendship I would normally talk to the person first. I never let it stop a love interest, though. I always thought it was pretty immature to get butt-hurt about someone dating your ex and if they got offended I probably didn’t want them as a friend anyway. Just by two cents, though.


  3. This is a tough one. I think all of us have fallen for the guy “we can’t have,” and there is something really romantic about it. But like you said – don’t let the IDEA cloud your head of what is real – is your friendship worth hanging onto? Was she really in love with him, or just jealous or possessive? Is this guy worth the effort? Only you can answer that.


  4. I always say about single life between 35-45… “The odds are good, but the goods are odd.” This just means there may be lots of single men, but they’re train wrecks, peter pan – mid-life crisis guys, or just nut-jobs. If a woman can just realize it’s not imperative to find THE ONE during this time… but to have fun and enjoy life, the playing field does open up more as men who’ve gotten divorced earlier, have started to settle down and be ready for relationships, their kids have grown up some, or they’ve worked on their issues… This is my experience… But yes – in a small community, things do get incestuous… tough NOT to date someone a friend has dated… That’s how it was in Aspen – a town of 3500… there was no getting around it.


  5. As usual, excellent, insightful, thoughtful advice. I’d like to add: A) how about talking to the friend before deciding anything, posing a hypothetical question to them B) Work on the assumption that nothing will come of the new liaison, how would things be with the friend and can you live with it?


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