He’s Best Friends with His Ex

Dear T,

Would you care if a guy you’re talking to is best friends with his ex-boyfriend?  Been talking to this guy for about a month now, and recently I met his group of friends.  After talking with the friends, I found out that one of them is his ex.  That kind of threw of me, because I wasn’t expecting to kick it with my almost boyfriend’s ex.  I can’t help but be bothered.  The man I’m talking to didn’t share any of this information with me.  When I asked him how long he and his friend dated, he said two years, but they’ve been broken up for three.  I’m just uncomfortable with the whole situation.  What would you do?

–  Not For This

Dear Not For This,

Thanks for writing to me.  Sorry to hear you were blindsided by your “almost boyfriend.”  After a month of dating, I know I for one would probably want to know from the guy I’m talking to that he is best friends with an ex. That’s some news that understandably takes someone a little time to digest. So I get you’re frustrated.

Before I go any further, let me recap my feelings on being friends with an ex.  When it comes to this argument, I happen to think you can’t be friends with an ex.  I believe you can be friendly, but not friends.  And there’s a difference.  Being friendly just calls for a person to exchange greetings when he sees an ex, not to act weird around him when in the same environment, and maybe even speak with the former love via a message every now and then.  That’s a strong maybe by the way.  If a message is sent, it’s more of a welfare check and the exchange of surface level conversation.  Plus, it’s done so on a rare occasion. But friendly does not include meeting up for drinks on a regular basis, going to each other’s birthday parties, and hour long phone conversations multiple times a week. Essentially being friendly means keeping a courteous safe distance.

Having said that, I, like you, would be uncomfortable with a dude I’m in a “situationship” with being besties with his old bae.  Especially, if I was hoping to build something long term with the guy I’m talking to.  In the back of my mind, I would feel sometime of way about my boo still being close with someone that knows him that intimately.  That knows him in a way I’m trying to.  Let me be clear, this has nothing to do with insecurity.  It’s about not wanting someone’s romantic past constantly thrown in my face, and having to wonder about whether there are lingering feelings between my “could be boo” and his ex turned bestie.

Now I know some people may read this and think, “What’s the big deal?”  Those in this school of thought are probably impressed the two guys that were in a relationship were obviously able to end things on good terms and remain friends.   These same folks probably even feel that this guy being best friends with his ex is a compliment to this guy’s maturity.  While I understand this perspective, I just don’t agree.

The following analogy may not sound the best, but hopefully you get where I’m going with it. If I purchase a used car I’m thrilled to now own, I don’t want the previous owner who lost the car due to lack of payments, constantly hanging around it.  I don’t want him telling me how to drive it. I don’t want him telling me where he drove it. I don’t want him to tell me how to keep it running. I just want to own my car, and I don’t want there to be confusion as to whose car it is.   Again, I know this isn’t the best analogy, but hope you understand.  Oh, and people don’t own a person in a relationship.  Or at least they shouldn’t.

Suggestions going forward.

  1. Sit down and talk with the man you’re hoping to lock down. Calmly explain where you’re coming from.  Tell him you wish he would have told you the news, and are a little uncomfortable with the friendship.  Under no circumstances should you present him with an ultimatum.  Don’t make him choose between you and the friend.  After only a month, you’ll more than likely lose that battle.


  1. If the guy you’re talking to reassures you that he and the ex are just friends and nothing more, and that any romantic feelings are gone, believe him. While him being besties with the ex may not be ideal for you, you can ease your comfort by hanging around your “boo” and his ex more. Spend more time getting to see their interaction, and perhaps you’ll see you can relax a bit.


  1. If you just can’t wrap your mind around the friendship, then perhaps this guy is your Prince Charming.

As always nothing but love,


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2 thoughts on “He’s Best Friends with His Ex”

  1. J says:

    Hi, I just discovered this website and found it to be really helpful. I am in a similar situation as the guy who wrote to you, except that the guy I’m dating told me about the ex from the beginning. My theory is that the ex is still in love with him. My guy moved to this country first, with the ex following him after a while. When they broke up, the guy still moved, I suppose they have made all the arrangements. That breakup was 4 years ago, after they dated for 4 years. A year after their breakup, they got reconnected and are now inseparable as “best friends”. Should I go on with this guy? I’m already falling for him, but if I would be certain I’m in the middle of something, I’d rather back out.

    Thanks for listening T.

    1. AsAccordingToT says:

      Hey J,
      Thanks for writing to me. I’m glad you find the site helpful. That means a lot to hear. In terms of your situation, I would advise you talk to the guy you’re dating and explain that you’re uncomfortable with his friendship with his ex. I suggest also, that you meet with him and this ex turned bestie to see up close how the two interact. After seeing how they are around each other, it may give you some perspective as to the true nature of their relationship. If you feel like him being friends with his ex is beyond your comfort level, then there is nothing wrong with walking away. But let that be a decision you make for yourself.

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