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How do I bring up that I dated his friend 3 years ago?

Tagged as: Dating, Friends<< Previous question   Next question >>
Question - (15 August 2011) 5 Answers - (Newest, 16 August 2011)
A female United States age 36-40, anonymous writes:

Three years ago I went on a few dates with a guy we'll call Andy. I was never really into him, although things went a little too far one night, but I didn't want them to so I left. We saw each other one more time after this and talked briefly, but the interest just was not there. I began dating one of his close friends a few weeks ago. I thought he knew about what happened between Andy and I, but now am not so sure. I mentioned how one of my friends is now dating her ex's best friend/roommate and he remarked that it was gross. Do I need to bring up Andy to him now? I feel like I'm hiding something from him now if I don't, since I no longer feel comfortable assuming he knows. At the same time it was three years ago, I can't change my past, and it wasn't a big deal to me or Andy (I would think Andy would have mentioned this to him at some point being that they're such good friends). I really like him and am afraid this may make him want to break things off with me. If I should bring it up, how should I present it?

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A female reader, TasteofIndia United States +, writes (16 August 2011):

TasteofIndia agony auntI guess I'd wait until you see him in person. It's not a huge deal, but it is probably better to be looking him in the face so he can visually see how not-a-big-deal it really is. I don't think the situation is desperate enough to warrant calling him on the phone right away!

Good luck, sweet!

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A female reader, anonymous, writes (16 August 2011):

I won't be able to see him for a few days. Would over the phone be acceptable or should I do this in person?

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A female reader, TasteofIndia United States +, writes (15 August 2011):

TasteofIndia agony auntI agree with the previous posters. You and Andy, it was short, didn't mean anything, etc. The only way that it will SEEM like it meant something is if you keep it a secret. So, rather than it coming out down the line and having your three-date-tryst with Andy being a super big deal, I'd just say something now and get it over with. With stuff like this, it won't be the fact that you dated Andy that hurts, it will be the fact that you felt the need to keep it secret and that will feel like lies upon lies for all the time you've been together.

Bottom line: this can be a big deal when it eventually comes out, or it can be a passing conversation piece if you are up front and tell him now. Best of luck, sweet!

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A male reader, serenity80 United Kingdom +, writes (15 August 2011):

I think you should bring it up. The reason is, if you don't, it MIGHT be something that this guy may have an issue with in years to come.

It is far better to get it in the open, and then you can leave it in the past.

I've just been watching an issue unfold with a friend of mine who has been in a relationship for five years with someone and he only found out recently that his girlfriend had slept with one of his mates before they met. If she had told him when they started dating maybe it wouldn't have been an issue, but now (to him at least) he feels deceived and their relationship is really on the rocks.

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A male reader, Will 77 United States +, writes (15 August 2011):

Any way it's done, it's better coming from you than Andy. Inevitably, it will come out.

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