Why am I so bad at this?

[Buranri]

I am straight terrible at dating. Not relationships - I have a decent number of friends, I don't really have a problem talking to girls. I'm kind of a quiet guy when there are a bunch of loud people around, but when it's smaller groups I talk more.

Dating, however... Completely useless. in 16.5 years I've had exactly one relationship, which lasted for two weeks. The only reason I was able to do that was because it started as a homecoming thing. I think total I've asked people out 3 times, and each one was either homecoming or some other dance. I am just completely lost without that crutch - like I said it's not really a problem talking to girls. I just start overanalyzing every single thing, trying to imagine how a date would go - in my mind, it's always really awkward - and then I never do anything. I'm so tired of being single, especially as the only single person in my group, but I don't see that changing anytime soon :/

[JUGG3RNAUT]

Think positive about how your date would go, if you think negative chances are it will end up like that. P.S. I hate being single too.

[xxbunkxx]

just find a girl that acts like you and it should work out perfect

[Buranri]

How would you choose here?

-A girl who you know likes you, but you are kinda "meh" about (I wouldn't mind dating her, but I don't see a long relationship happening).

-A girl you want to date, but don't know if she likes you back.

And once you choose... how the hell do you ask them out? I still can't get over the feeling that a movie is kind of old, or weird, but idk.

[Dimitri]

How would you choose here?

-A girl who you know likes you, but you are kinda "meh" about (I wouldn't mind dating her, but I don't see a long relationship happening).

Forget her....she will be fine as a friend.

-A girl you want to date, but don't know if she likes you back.

Be nice to her, ask her if she wants to get some coffee or something....

And once you choose... how the hell do you ask them out? I still can't get over the feeling that a movie is kind of old, or weird, but idk.
Coffee, that is how it has worked for me....

[Buranri]

Ugh. This shouldn't be so damn hard, but it is... I've always thought I would know when to ask someone, and in my limited experience it worked like that. I knew when to ask my one girlfriend to homecoming, it felt natural kissing her and asking her out before that. But I've never been able to find that with anyone else. Have I just not found anyone worth dating yet, or am I going about this all wrong?

[Buranri]

Huh?

[paradox]

Hey look man, I was in your same predicament a couple years ago. And don't downplay a movie as a first date, the reason why it's so "overused" or "old," as you put it, is because it works. You don't really have to talk that much so it's actually LESS awkward and you have something to talk about afterwards to get some conversation going. I would say movie first, then coffee afterward at some sort of cafe. Then you have the movie to talk about, what kinds of coffee and food you like, whatever.

As for actually asking out a girl, I would say to avoid the actual phrase "Will you go out with me?" It's a little blunt and vague, so unless you do it in a really creative way then I would avoid it. A nice casual way is to start talking about a movie in theaters that you think you'd both enjoy seeing. If she seems interested in it you casually state, "Hey, we should go see it together this weekend, are you free Friday night?" Or something along those lines. It's casual, it's smooth, and if things go well at the movie then you make plans for another date and then a relationship's started.

Hope this helps! ;)

EDIT:
Ask either a) in person, or b) over the phone through an actual call (NOT texting or facebook).

Finally, be positive and confident!!!!! I CANNOT STRESS THIS ENOUGH