First of all, I'd like to thank you guys for all of the awesome advice. I've been a sedditor for about a year but today I'm using a throwaway account because this is sort of embarrassing.

Ok Seddit, so here's what's up.

I have a really strange problem. I can't approach girls with the intention of dating/sex/etc. Now, I know what you're thinking - he just sounds like a huge wuss. And you're right, I probably am. But the problem is deeper than that. You see, I'm a really social guy. I can easily hold a conversation with anyone, guy or girl. I'm not even afraid to come off as strange or awkward. However, the stipulation is that I can only keep my cool when I'm obligated to talk to people. You know, when it's situational.

I'll give you an example.

Say there's a beautiful 10/10 girl in my college class. Normally, there would be no way in hell that I could approach her. Just no. I would feel too... obvious. I would feel like she could see exactly what I was doing. Almost as if she knew I was planning the approach days in advance. I feel this way mainly because there would be no other reason for me to talk to a complete stranger.

Now, imagine that, just by chance, my professor forced me to work in a group with the aforementioned girl. In this case, I could easily talk to her and have a great conversation. I'd be like "Hey! You're in my group. Let's chat." I would be alpha and make a move right away. The outcome wouldn't even matter to me. I'm not really concerned with rejection in that sense.

When I say obligated, I also mean justified. Like, having a real reason for initiating conversation.

To sum it all up, I feel too awkward when I approach girls. In the back of my mind, I always think "you have no reason to talk to this stranger" and it makes me feel stupid and desperate. At the same time, if I am obligated to talk to a girl because I have a legitimate reason, then everything is fine. It's almost like I feel justified in talking to her. It makes for a relaxed and natural conversation. I could just wait around for the perfect situation but that could take a lifetime.

So my question is, what the fuck is wrong with me?

Also, while asking a stranger about the weather is technically a legitimate question, it's still cheesy and makes me feel obvious. So any advice or tips other than that would be tremendously appreciated!

Rock on