A
female
age
30-35,
anonymous
writes:I have a close male friend who I basically grew up with. He's very sweet and funny when you get to know him. The problem is that he is painfully shy and not very attractive. He's never asked anyone out and the girls around here won't give him a second look anyway. I know because I've tried to fix him up. I know he's still a virgin too. I am starting college out of state this fall and we won't see much of each other anymore. I'm seriously thinking about offering to have sex with him before I leave. I think he would probably go for it and it would be good for him. Maybe he would get some confidence from it and come out of his shell. Is this really a good idea? We're basically going our separate ways after the summer anyway, so I'm not worried about the friendship getting too weird. I'm not attracted to him but I care about him and wouldn't mind doing this for him. Would this be a good thing or will he think I feel sorry for him? That's the only thing I don't want.
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male
reader, daletom +, writes (1 August 2008):
Speaking as one of those shy guys - If your having sex with him DOES "give him some confidence" it will only last about 90 minutes, max. That's if he isn't very bright. Somebody with average intelligence will see through it faster than that. Once he realizes that, it's hard to say exactly what will happen to him but I don't think it can be anything good.
There's a famous gag that Charles Schulz used over and over in the "Peanuts" comic strip. Charlie Brown is going to kick a football field-goal, and Lucy is the ball-holder. (This is about American football, for you folks who aren't in North America.) As Charlie Brown rushes to the ball, Lucy yanks it away at the last moment and in his attempt to connect, Charlie Brown does a flip and lands flat on his back. What you are suggesting in this post isn't far removed from that cartoon caricature.
Again, speaking as one of those shy guys: If you are sincerely concerned for this guy - not necessarily in any boyfriend/girlfriend or romantic sense, but just as one human person trying to help another - make an effort to include him in activities with your friends, where he can practice and gain skills interacting with people. Things like "Bob and Sue and Jim and Dan and I will be having lunch at the park tomorrow - why don't you join us?" or "A bunch of folks I know at church are going to the minor-league ballgame next Tuesday. It's always a lot of fun 'cause you're right next to the players - why don't you come along?"
Don't try to set him up in anything like a real date. Quite frankly, folks your age haven't developed the skills yet to be very good at it. (That is NOT an insult, just a statement of where you are in life.)
But something that may be VERY good for your guy friend is bringing his situation to the attention of an older adult who knows your friend fairly well. Somebody like a teacher, a coach, a Scout leader, maybe even his Uncle or a (significantly) older brother or sister. Say the things you put in your post - that Tom (or whatever the guy friend's name is) doesn't seem very happy in his position, and would this older person know someone who could interact with Tom and help him be more confident? It may even be another guy, rather than a girl, who gives Tom what he needs to have relationships with the opposite sex.
And don't worry about Tom's virginity. With US$50 in his pocket, Tom could check off that box in short order - and be even more marginalized when it's over with than he is now.
A
female
reader, anonymous, writes (1 August 2008): What if you get pregnant? its not the most respectable of suggestions to sleep with your best friend. Im sure that he'll find a girl and plus i think losing the virginity part with your best friend is wrong, he'll meet a girl, get married and then lose it this moment is just the wrong time for him and you. Making it highly awarkwark if you do come back into town. You might even lose him over it, keep your feelings of losing his virginity to urself it might just hurt you and him
Good luck
x
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A
female
reader, Angela.B  +, writes (1 August 2008):
 I am going to put ethical questions to one side (such as is it right to have sex with someone we don't love) and presume you have thought about them and are happy with your own answers.
The danger is he will misinterpret having sex with you as a sign that you love him and want to be his girlfriend. If his confidence is that low now, how will he feel when you then have to break his heart and say "actually, it was sympathy sex"? That could kill any self esteem that he does have!
I could also wonder if you say you care about him this much, that he's sweet and funny, and that you would sleep with him, just what are your feelings in this? Could it be that you really do love him, but are perhaps worried about what friends would say (after all, he's not that attractive etc)?
Possibly you don't, but if it has a stranger questioning it you can see how easily he could get confused by it! And if you do, then perhaps you owe it to both of you to initiate a relationship?
No doubt having his first girlfriend who likes him enough to sleep with him will improve his confidence. How you could fill that role without him realising it was all false I don't know, so I don't think it's a good idea however well meaning your intentions are.
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A
male
reader, Danielepew  +, writes (1 August 2008):
 Yes, he might feel you feel sorry for him, and also that you believe he can't get a girl by himself. Also, if you're friends only, and you're leaving, I wouldn't complicate things. What if the man doesn't get anyone else later, as he has a problem, and then wants you back?
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A
male
reader, anonymous, writes (1 August 2008): I wouldn't go for it. As a man, he may feel an ego boost, and a satisfaction from the event. But afterward, when you leave (sounds like permanently), he is just going to be alone as ever, and feeling down because even his closest friend who actually cares about him doesn't think he's worth keeping around as a partner. It may make him feel good in the short term, but probably worse in the long run.
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