Dating my friend’s ex

Dear Guys,
Well, I have a best friend who I really like, but I don’t know how to tell him. We have been talking a lot and I’ve been getting mixed signs from him. Like he’ll just step out of his way for nothing to try and get next to me or talk to me. It’s a bit more complicated than just that. He used to date my other best friend and I don’t know what to do. We don’t keep in touch like I do with the guy I like, but she and I still talk and I feel a bit guilty.

I really like this guy and I have a lot of trouble trying to get him to understand that since I’m really shy about my feelings especially if it’s concerning a guy I like. How can I tell him I like him without causing my friend to dislike me?



Dear Adrastea,

Thanks for writing.

Good for you for caring about your friend’s feelings. In this “ME FIRST” world, that’s refreshing to hear.

Here’s the bad news. If you want to pursue this guy, it’s possible you are going to upset your girlfriend. That’s not for certain, but it might happen.

If you’re feeling guilty, why don’t you call her up and ask her out to lunch. Talk with her. Tell her that you really like her ex, but you don’t want to ruin the friendship you have with her. She may not even care, especially if she’s moved on and is dating someone else. Either way she’ll appreciate your honesty and that you cared enough about her to let her know. We’re not saying ask for her permission. You don’t have to do that. But if you value the relationship you have with her, it’s worth talking to her.

Like we said, you can’t control other people’s reactions. If you spend your life worrying about how your actions impact everyone around you, you are going to be an unhappy camper. It’s great to be aware how your decisions affect others, but sometimes you just have to do what makes you happy. (We realize this goes against our original statement, but it’s all about finding the right balance.)

We’re sure you’ll do what’s right. You have a good heart Adrastea.

Good luck. And keep us posted.


5 Comments on Dating my friend’s ex

  1. Well it’s nice that you are considering your friend’s feelings but I think you are going to have to choose your colours – and really work out what is important for you.
    Whether or not you date him, he isn’t going to go back to your friend is he?
    Do you like him enough to risk a friendship?
    If you do, be open with your friend. What she chooses to do with that information is her business.
    Good luck!

  2. I like the advice from the guys. It really is the right thing to do in talking to your friend. Either way, make the decision for you and if you decide to open the door to more than friendship..clue the guy in. Some don’t take subtle hints well. It will save a lot of time and mixed singles. Good luck to you!

  3. I think your response to Adrastea is right on target. One of my policies that I’ve always stuck to, no matter what, is to stay away from my girlfriend’s boyfriends, husbands, and exes. In my opinion, there are so many possibilities in the world, there’s not a man alive who would be worth ruining a good friendship over. Good friends will be forever–and a date with a man is simply not worth wrecking that. I hope Adrastea listens to your good advice and talks to her friend first. My guess is that the friend will be upset–even if she might not say so. We tend to hang on to our old relationships in that way–at least most people I know do.

  4. Great advice! šŸ™‚

    Personally, for me, friends’ exes are a taboo. I put a lot of value in friendship and I wouldn’t even think of going down that road. I have been in a similar situation and without revealing my dilemma to anyone, I chose not to get involve. I am not saying it is wrong – at the end of the day each person have to take responsibility for their own actions and decisions. I prefer no complications.

  5. All of your advises are good till you starting to like your friend’s ex. Yeah you can said is taboo and policies, but you can help if you starting to like one of your friend;s ex. specailly if they broke up for over a year and she has other boyfriends in between, I said Go for it., Think about you and your feelings,,,

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