Can I Date My Best Friend’s Ex?

Posted by in dating after divorce, first date success, love after 40, single women over 40 | 1 comment

Hi Sandy,

My best friend broke up with her boyfriend, George, three months ago. I have always had a little crush on him, but I would have never made any moves on him while they were dating. The truth is, I never saw George and my BFF as a good couple. They just didn’t really seem to work. I guess that’s why they broke up!

I hadn’t seen George in months. He kind of disappeared after the breakup. But recently, I’ve been seeing him at the local coffee shop almost every morning.

He always smiles at me and we exchange a few flirtatious words before parting ways with our lattes. 

This morning, he asked me out! I am feeling mixed emotions. On the one hand, I am so excited to go out with him, but I’m also conflicted. Even though my girlfriend broke up with him, I feel awkward dating George so soon after their breakup. What should I do?

Can I date my best friend’s ex? Or should I just move on and try to find someone less controversial to date?

Help me please!



Hi Maryanne,

This is such a great question. You want to date your best friend’s ex, and you don’t want to hurt your BFF’s feelings.

I will share a story with you that reminds me a little of your situation.

Many years ago, my roommate dated a guy for a few months. She was madly in love with him. The feeling wasn’t mutual.

He soon met another good friend of mine and fell head over heels in love with her. He dumped my roommate for my other good friend. A short while later, they got engaged.

My roommate was devastated. My other friend was on cloud 9.

When I got invited to the wedding in Chicago, I felt a torn allegiance between the two. Was it a betrayal of my roommate to attend the wedding and be happy for my other friend?

I ended up going to the wedding. I think I made the right decision.

While my story and yours are not exactly the same, the principal is similar.

When a relationship is not right for two people, it’s just not right. Even though one person might be devastated at first, they will eventually move on and meet the right person. It takes two people to make a relationship work, and if one is not into the other, it’s actually a favor to the other person when the breakup happens.

My roommate went on to find a husband a few years later. He was much better suited to her. He loved her dearly. And he had a sexy British accent!

If I were you, I’d say YES to the ex, and I’d also be very frank with your BFF. The advantage you have is that she broke up with him. But in any case, clear and honest communication is always best. I am pretty sure she will give you her blessing!

Let me know what happens.




1 Comment

  1. While “true love” really should win out, and indeed “all’s well that ends well” – as with your friends, Sandy, and perhaps this letter-writer too – I propose that there are a few additional points for readers to ponder before blithely saying “yes” to a best friend’s ex. A key factor here is that the best friend apparently initiated the break-up; otherwise, the wounds might still be quite fresh at the three-month mark. Also, how long were the two a couple, before their break-up: four months… or four years? If it was a serious, long-term relationship, don’t be shocked (regardless of who initiated the breakup!) if the best friend feels hurt, and even cools down the friendship for a while. Because she may be reeling with newfound insecurities and jealousies as she questions, for the first time: “So was George harboring a simmering crush on my always-around, untouchable, beautiful friend… and maybe vice versa? Was THAT part of why our romance/intimacy never felt quite right?”
    Yes:it happened to me. And even after all the decades of my “maturing” and forgiveness, resumption of warm friendships, full understanding of what came to pass and full recognition that he was NOT the guy for me… I still maintain that they wronged me and disrespected me in how quickly they took up with each other. (They only lasted a few months.) I can still remember how blindsided and publicly humiliated I felt, and how long it took me to regain my wrecked self-esteem – over and above the sad ending of a six-year first love that we’d declared was “forever.”
    Yes, true love SHOULD win out, and therein, friends’ exes should not be off-limits; at some point, y’all just need to get over it and move ahead with your lives. But in the first months… let’s hear it for acting carefully and compassionately, and communicating honestly. Our best girlfriends are among the most precious relationships in our lives.

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