uhhh, why can't you just hang out with him a lot less than you do now?

why are you mr. matchmaker?

why can't you tell your friend of 20 years that it annoys you how he bitches about his life all to the time?

tell him it's a downer, and that if he insists on continuing to be so negative you most likely won't hang out with him as much.

In the same sort of situation so I am very interested to see what kind of advice you get.

My best friend (we're both 23) is doing a little better as far as being successful goes (he is currently in grad school and has an internship lined up etc.) but socially he is a complete liability and I find myself somewhat avoiding bringing him along when I go out with other friends. He doesn't start a conversation with anyone unless I introduce him first and his game is so bad that listening to him try to talk to girls makes me bruise from facepalming so much. I can't imagine ditching him because we have been through so much and he is about as loyal of a friend as someone could ask for but all my attempts to try and help him be more outgoing/confident just lead to him complaining/feeling sorry for himself/dwelling on the past/etc and it becomes so awkward that I try to change the subject as quickly as possible.

I feel like the biggest thing is to just get him over the hump of the unknown so he sees that picking up a chick isnt some insurmountable task. Would it be completely evil of me to just pay some girl to let him pick her up? haha. Not full out hooker or anything, but basically have a girl try and encourage an approach and then pretend like all the lame **** he is saying is charming her.

you really need to use some names in this story. or fake ones, something.

in any case, i suggest you keep this friend so you can always feel good about your own life.

The moral of this story is that anyone who gets drunk and bar hops is a ****ing idiot.

I used to have a douchebag friend like this, but he was my best friend for only a couple of years. We eventually stopped being friends after I punched him in the face and moved out. People change and it's ok and understandable that you no longer like him or as 2pac would say:

Cause time changes
and love changes
and beat friends become strangers

How good can YOUR life be, if you're hanging around with clowns like these?

Cliff Notes:
Your friend is gay. You're other friend is a douchebag.

Wasn't that Nas?

I love that there are 102 total votes, and 51 total voters. (as of now, obv)

This is exactly what I was thinking. He is like the comic relief while the other guy is just a boring loser.

Honestly, if he's still this intimidated by women at 26, there's a decent chance he always will be. It's not like he'll turn 30 and all of a sudden have confidence. If anything, the opposite seems more likely - he could retract further into his shell and just give up. He'll have to take the initiative if he's going to change things. You can't do it for him.

Yeah, you can make it clear to him that you're not interested in listening to him complain. That's a lesson he needs to learn. Next time you hear him complaining without making any attempt to improve his situation, let him know that you're not his mother and you don't give a ****. That's harsh but that's what he needs to hear. If you're his friend you'll help him only when he's willing to help himself, but you're not a shoulder to cry on when he's being pathetic.

why the **** do you care if your friend can hook up with women or not? why is this "the last straw?" do you really judge who your friends are on shallow **** like that? jesus christ dude, if he's a cool guy and fun to hang around, really, who cares? if he's horrible to be around and is a douche, i'd say sure, cut off contact with him, but from your own story it seems like he's at least good at talking to women and i gotta think he's not awful to hang around becuase you've known him for such a long time. be easy on the dude, jeez. I would never want to be your friend. also, way to suck at writing, you list at least 3 or 4 "other friends" and make no distinction between them besides the word "other" include fake names or at least friend 1, friend 2, etc., ffs. jesus. i was so confused figuring out who was doing what, until I realized I didn't give a ****. your friend will get laid when he gets laid, it really doesn't concern you, like at all. i could care less who my friends do or do not ****.

Intervene now before textbook case of this:

everybody just stay calm now.

but youre right.

err... maybe he just didnt feel comfortable ****ing her that night?

how does it concern you?

lol wat

in a thread full of fail, this post takes the fail cake.

Id rather be a drunken 26 year old virgin than married @ 26

Story cheered me up. I can't imagine why you'd want to get rid of this guy. Seems way more likely that hes gay than "scared of the unknown." That makes no sense to me at all.

What does this have to do with your decision to "stick by him"? Call him out for bitching about his life or w/e if that's the problem.

That'd probably give him some short-term confidence. Might as well go full out hooker though. I'd probably just hire Good2cu for expert PUA coaching....

No. Being bad with women is not evidence of being gay. Imagine that you are a 26 year old virgin. Think about how easy it would be to build up your virginity in your mind as a huge problem. This is due to the way getting laid is connected to social status in our society. Witness the OP's attitude about his friend's virginity, which really doesn't affect him at all, as an example of how important it can be. The fact that it is seen as such a problem makes it difficult to act naturally and smoothly.

Now imagine the anxiety that you might feel as you get close to sealing the deal with a girl for the first time. You are 26 and will be expected to have significant sexual experience and to perform accordingly, but it's almost a lock that you won't be able to. This could reveal your status as "loser." It makes perfect sense to be scared in that situation.

There's no reason to suspect he's gay without evidence (e.g. femininity, finding gay porn on his computer, etc.)

I suggest you get him to roll... it will increase confidence and if you don't want to bump uglies on E then you never will...According to a health class I took a couple years ago. I bet if you get him laid he would get a real job as well. What motivation does he have to make money if he doesn't want to have sex or at the very least fund an addiction? Honestly the best thing you can do for the guy is get him laid. If you have to go pro to make that happen for him by all means do it. If that doesn't work then find an addiction for him to get his ass motivated to get a real job and then intervene and rid him of the addiction. Then he will have a good job and not live at home anymore. Because it sounds like he's addicted to bitching and being a bum.

It sounds like you don't really know what it means to have a friend. He'd be lucky if you quit hanging out with him. You don't seem to have a problem with your other friend who gets kicked out of bars at 26 so maybe you're the one who needs to reevaluate things.

It's obviously this. If you want to get him laid, get him a hooker so he can just get it over with. Since she's being paid he can feel better about her not judging him. Maybe he isn't moving foward in his life because he is depressed ?

Having known a couple late stage virgins in my day, I'm pretty skeptical about the value of this approach. Paying somebody to **** you is not going to do much to allay your concerns about relationships (if anything it might confuse you even further if you haven't succeeded in having relationships at all). This approach seems good only if you think that the primary concern of the 26 year old virgin is just the raw mechanics, but I don't think that is the case pretty much ever.

The OP's thinking seems to be that the situation with this girl is irrevocably blown, but I don't see much reason to think that. Failure to take her home and bang her that night is problematic if your entire goal framework is to get the dick wet immediately and learn proper technique for closing random bar sluts, but there's a better than average chance that isn't what 26 yr. old virgin wants, anyway. If she's as into him as OP suggests, he probably has a reasonable window to keep moving before things get weird, and I think letting things happen organically for the most part is the best thing that could happen to OP in this particular context.