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age
41-50,
anonymous
writes: I have had an infrequent casual sexual relationship with a friend of a friend. He is the platonic friend of my girlfriend. Lately, I get the sense that he might want to deepen the relationship with me. I am not opposed to this and at times I feel like giving it a try.My girlfriend who introduced us has known him much longer. When we started having a casual relationship though, she began highlighting all his worse qualities and framed his attraction towards me as "he tries to sleep with all of my friends." She can be competitive when it comes to men, but it's a personality trait I'm used to so I overlooked her warnings. But,to be fair to her arguments, he has been a pretty undependable and a sometimes an awful friend to her. I've heard her long list of horror stories about him. He didn't pay bills when he subletted her apartment years ago when he was 20. She flew to the UK to meet him after agreeing to meet, but he failed to show up and she was stuck in London with no place to stay. Recently they made plans to meet up in NYC, but when they met there, he asked her if she wanted to go to a party in another city. He's terrible at planning things. She wishes he would respect her more.I guess I'm conflicted. When we were together recently he found out I knew about a few of the "crimes" he'd commited against her years ago. He seemed embarassed and said something like, "She tells you about me? So now you know I used to be kind of flaky. Well, at least you go into this with your eyes open."When I pointed out the benefits of our current arrangement, he said I was being "cynical."Should I give it a try or pass him up? I'm feeling like I don't really want to do casual relationships anymore either? He has never stood me up when we arrange meetings. But I've never really asked him to be dependable and maybe that's why I still like him.Advice? Reply to this Question
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, angelDlite  +, writes (4 January 2011):
 hi
are you sure your friend isn't romantically interested in him herself? after all if he has been such a nightmare of a friend to her why does she still keep him as a friend? you make up your own mind, depending on how he treats you, not what she says he has been like towards her, and she seems to be dredging up horror stories about him from YEARS ago too. look if you wanna give him a chance, go for it. if he ends up hurting you, your friend can say 'i told you so' you'll be upset for a bit and then you'll get over it, but at least you will know you tried. if you listen to her and pass him up you will never know what could've been
xx
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