I have a friend that is twenty years old, but he has never had a girlfriend. It’s not from a lack of trying on his part, mid you, but he’s a little eccentric, and girls have never really paid that much attention to him.
He’s a really nice guy, and been a great friend to me for a long time, so it’s painful on my end to see him try so hard to get a girlfriend and get rejected again and again. It’s gotten to the point where he’s starting to think there’s something wrong with him, but I don’t think that’s the case.
When I said “eccentric” earlier, I just meant that he’s a little socially awkward. He’s got very poor social skills around new people and isn’t very athletic. All of his skills are intellectual ones rather than physical ones: writing, reading, making jokes, etc. From my end of things, I can see why a girl might be put off at first, but after getting to know him, it’s very easy to see that he’s a great guy.
Is there anything that I can do to help him? It just frustrates me so much to see him keep getting hurt like this.
LemonVibe 
[First of all, you sound like an awesome friend and that you really care about this guy. This is a hard one, though. You can be there for him and encourage him, but you can’t change him. I agree with Eleanor, though, the more socializing he does, the easier it will get.
You said that he’s not athletic. Does he have other interests that could involve socializing? Music, art, coffee shop lounging? Maybe if he’s in an environment that he’s comfortable with, he might have an easier time opening up and socializing.
[Can you invite him to hang out with a bunch of people with you? Having you there will probably make him more comfortable, and the only way he’s going to get better at interacting with people is to practice.
[I have a friend like this! He often gets down on himself for not being “wanted” by girls, which gets frustrating for me because I’m not sure what to say to change his mind. Experience shows that girls don’t want to date him, but that doesn’t mean nobody does. Just not the girls he’s met. My friend (not necessarily yours, but mine) has kind of high standards. It may sound harsh but I think if he looked for someone a little less “perfect”, maybe a little more quirky or not supermodel pretty, then he’d have better luck. But It’s nearly impossible to tell someone that nicely, without them hearing “you’re ugly so you need to look for uglier girls, lower your standards…” That’s of course not at all what I’m trying to say, but that’s how he’d hear it.
Maybe your friend is trying for girls that aren’t his type, but that he’s built up in his head to be the girl he wants to be with. Help him by trying to introduce him to people that YOU THINK would be good for him. You’re his friend, and I assume a very close one based on how much you care about him. Introduce him to people. Not just to a new girl, but to a girl that you have told about your friend, who thinks she would like him, who you think would at the very least be someone he could learn from.
At the heart of all this is confidence. He may be super smart, funny, and charming to you, but if he’s too nervous or self conscious to be that guy in front of other girls, he’s going to continue to strike out. They say “you have to love yourself in order to be loved by others” and your friend really needs to understand that and live by it. If he’s as awesome as you say, he deserves to find someone, and he will.
[Has he ever considered online dating? It doesn’t seem like it’s as frequently done among college students, but it definitely seems like it would help to highlight his stronger attributes.
If he’s shy around new people, he could get to know them to some degree before they even meet. He’s better at reading and writing and making jokes, which is something that seems like it would come out more in electronic communication. If he meets a match, he might still have to struggle with the things that he usually does, but at least he’d have a nice cushion and starting point to fall back on and make him feel more comfortable.
[As someone who is rather eccentric with poor social skills, I feel for your friend.
However, I’d like for your friend to meet my good friend who helps me socialise at parties. He’s an older gentlemen and he’s not to everyones liking but he really does blend well with others and is the life of any party. He’s always helped me with girls, but sometimes I only need a little bit of his help to get comfortable.
Anyway, his name is Jack Daniels and he’s pretty easy to find.
On a more serious note, you could get your friend into a situation that he can shine in with other people there, perhaps grow his confidence that way?
[What element is he most comfortable in? Even if it seems lame or embarrassing, if he’ll be at his best that’s the place to look for like minded people.
I might be assuming a bit about your friendship but do this with him even if you personally find it lame or embarrassing. At least at first. It shows support.
Anyway if he is comfortable and having fun he’ll be projecting his best and seem more attractive to the opposite sex. You might have to find this place, but you might really like it yourself too.
[Does anyone NOT know someone like this? I have had several friends who have fit this bill, and they would probably say that I do as well. Right now, they are ALL married. For most, it didn’t happen until they were in their mid/late 30’s. In each case, however, they found exactly the right person… the perfect match for them. Please give your friend the advice I gave to mine:
Enjoy your single time. Travel. Join clubs. Engage in your hobbies. Focus on your education. Once you meet “Miss Right”, you life will change (for the better, mind you) but you won’t have those opportunities to focus on just yourself again. Also, by engaging in those things that interest you, that is most likely where you will find the right person. For example, if finding a girl who is a Christian is important to you, find a church that has a lot of social activities and become a part of it. Your not gonna catch a trout in the bass pond no matter how long (or well) you fish.
Your friend will be fine in the long run… help him have the faith to believe that.
[I agree with all that has been said so far. Also, the guy is only 20. Plenty of 20 year olds have never had a girlfriend, so he should try not to get down on himself about that, although it may be hard if his friends are in relationships. Eventually he will find someone who sees and appreciates all of his good qualities!
[@Dong: This is about you, isn’t it?!?!?!?
But seriously, I agree with what’s been said. Get him in a group setting, and just make him comfortable. My only other piece of advice would be to tell him to stop trying. If he just interacts with women as friends, they may start to see him like you do. He may be coming on a little strong, which is putting women off.
[I second Rez’s advice to stop trying so hard, and also the advice about online dating. I know they’re contradictions, but I think they both work really well. Like Margaret Charles (ha!) says, the medium of the internet will give him a chance to let his strengths show, and hide his weaknesses a little, or at least buy him some time. Maybe getting comfortable with someone online first will make in-person interaction easier for him.
The not trying so hard thing, though, is really important, especially for someone you describe as intellectual rather than physical. Is your friend “geeky”? If he’s already got a lot of things about him that make him “less desirable” to women, he doesn’t need to add a desperate appearance to the list. Believe me, from personal experience, nothing repels girls faster than the stench of desperation.