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Uncomfortable about boyfriends womanising friend

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I have been with my boyfriend for about 6 months now and it has been going really well. We were friends for about a year before we got together, thereforeeee I know a lot about his past, which, to say the least is quite colourful....


He was quite a womaniser in his youth (20's) and so were most of his buddies. He is now older and wiser (30s) as are most of his friends. They have all settled down with partners, wives etc. As has my boyfriend, He loves me dearly and talks of marriage, kids and a great future together.


BUT.... There is this one guy I haven't met yet but I have heard about. This friend of my boyfriends is still behaving like he is a 21 year old punk- womanising, cheating, lying and basically sleeping with different women as often as he can. He has a girlfriend who knows nothing about this who lives out of town.


The thing that is the REAL kicker for me, is that back in the day, he and my boyfriend used to hook up with random girls and have threesomes and god knows what else.. (Makes me shiver just typing it). These are all things I found out from my boyfriend directly telling me the (at the very start of our relationship).


Since we have been together, he has met up with this guy about 2-3 times. Each time I basically have voiced my disapprovment at this guys behaviour and my discomfort that my boyfriend seems to be associating with someone like him. I just let him know it made me a bit uneasy that they are sitting at a restaurant and this friend is relaying all the sleazy details of his last encounters to my boyfriend.


Now the icing on the cake is that my boyfriend wants me to meet this friend for dinner/drinks tomorow night. He mentioned it out of the blue..they had dinner plans for tonight but they fell through, so my boyfriend suggested all three of us meet up tomorrow night. I have told him that I am super-uncomfortable with that idea....just sitting there knowing that they used to f$#@ around together makes me feel ill. My boyfriend thinks I am being silly and that it is all in the distant past, thereforeeee I should just let it go.


Am I being silly, or do I have a right to feel weirded out?

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I'd would feel weird sitting there knowing what he has/is done/doing. If i was you i would go, and see how things turn out. He could of changed! (Or maybe not.) If you don't like him, either leave earlier or stick it out for your other half and just tell him when you get home that is no go ever again. Don't knock it till you've tried it they say! Give him once chance and one chance only. Hope everything goes ok.

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Personally, I don't think you should be judging him based on his sexual life.


Sure, he may of slept around when he was younger... and he may still be, but that doesn't count for the quality of himself. What he does or has done in the past is his business and you should be judging him on merit of his personality, not how many woman he has slept with.


Give it a shot, see how things pan out... If you flat out refuse to meet him your boyfriend with think your being judgemental. Do you have any other reasons not to meet him?


What have you got to lose?



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Really, what difference does it make to you if your boyfriend has this womanizing friend? If they were going out frequently for nights on the town, drinking it up, going out to clubs, etc. it would be one thing. But by your own admission he has only met this guy a total of two or three times in the six months you have been a couple. This guy is the only holdout who hasn't grown up and is still sleeping around. The rest of your BF's friends have all moved on to more mature and stable relationships.


I think you are uncomfortable with your own BF's shady past and his friend is a reminder of that.


The thing that is the REAL kicker for me, is that back in the day, he and my boyfriend used to hook up with random girls and have threesomes and god knows what else.. (Makes me shiver just typing it).


Key part of that quote is "he and my boyfriend". Notice your use of the word AND.


If you don't approve of your boyfriend's past because it doesn't mesh with your values - you shouldn't be with him.


If you trust your BF so little that you fear this friend will influence him to behave in the same way he does - you shouldn't be with him.


On the other hand, if you truly accept your BF's past and that he has changed for the better, and if you trust him not to behave the same way this one shady friend does then I would advise you to stop telling him you disapprove of his friend and go meet him.

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It's his past- and that's where it should stay. Everyone has done things in their past that may have been seen as a bit wild or different, it's part of experimenting and growing up. However, that was before he met you, and he is with YOU now, and it's serious, he's talking marriage and family, and those are all good signs.


I think it's a good thing that he wants you to meet this friend. It means that you are very important to him and he wants his friend to meet you, get to know you, and see that he too is settling down a bit and happy and in love.


I see this as a positive thing.

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Thank you all for your words of advice. I do agree at that the end of the day I am being insecure. I have worked through most of my issues with the trust/commitment/fidelity etc with my boyfriend, and I agree that I shouldn't judge his friend- i don't even know him.


I think I will just have to meet him and see how it goes...!

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