Troubles dating (girls' perspective greatly appreciated please!)

I have a lot of trouble with women. I'm going to explain a little about my history to help understand where I'm coming from:

I was extremely shy up til about 11th grade, I met a girl, long story short she became my girlfriend but after a year (including prom and occasional outings) I just never kissed her.. I had a moment at prom but was too shy.. so after a year of being together she dumped me because she thought that I'd be a better friend instead.. At which point I hit a huge depression and months later I not only recover, but I change..

I start to make friends, and 2 years later I have maybe 150 contacts.. I also become a photographer. I start to explore my creativity. I have moments of frustration with women that lead to little flings involving only making out. I pursue my drawing, ideas, other things.. 3 more years fall off the calendar and I now have about 450 contacts from business people to friends to people I contract. I'm 24 now, and it wasn't until this year that I got really intimate with a girl, but then found out she was using me (wanted me to draw a portrait of her, photograph her.. she was a beautiful girl with a disappointing personality)..

So my problem is this:

I'm not really the type of guy that looks for one night stands; I'm looking for a relationship. But lately I've been feeling a little desperate and it's difficult for me to help it. I'm EXTREMELY naive to body language.. I make friends because I guess I can be funny, smart, confident, and keep up with many conversations.. but that's familiar ground.. I'm not very familiar with flirting, and honestly that part of me still feels like a teenager.. I'm shy, and inexperience makes me insecure.. especially intimacy.. so I feel like I've lost a LOT of possible dates to that.. on the other hand I've tried to look for flings and again, I'm just not confident enough.. everyone else seems to have a lot of sex around here but not me.. I feel like a 4th grader stuck in a 10th grade class only because I'm the same age..

I feel very different from most of the people I meet.. I've been told that artists are anomalies.. most people would think I "get all the girls" because I draw professionally, professional photographer, I've had poetry published, and starting to design my own furniture.. but the reality is that I'm too analytical.. I "wait too long".. I don't see the signs.. and it's really frustrating trying to find a companion :/.. any insight please ?

Updates:
if you have time, you can read my prior question involving a specific case/frustration with a girl..
Is there a way to delete this question? I don't think it needs to be up here.. sry..

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Most Helpful Girl

  • You seem like a really great guy, maybe you're just not looking in the right places? Try approaching girls you wouldn't usually or doing something you wouldn't normally do, you know? You say you have no problem making friends, so how is that any different than meeting a great girl? Just go for it. You got this(:

    You're pretty interesting, we could use more guys like you around. Lol

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    • I've been trying to do that.. to an extent I have, I'm trying not to think about it so much and focus on my work/career then maybe something/someone will come along.. I have a crush on a girl in a way that I have not for a long time, so I'm going to really just get it "out there" and tell her just that.. in a confident way of course.. heh. thanks for understanding.. I wanted to delete it thinkin it sounds all wrong :/

    • I don't know, I've always thought it better not to go looking for someone/love/whatever, it seems like it's just something that should just.. happen. You know? So do what you got to do and whatever comes along, make the best of it(: Good luck with this new girl! &no it doesn't sound wrong at all, maybe people are just intimidated by the length to leave an answer. Lol

    • It seems finding an ideal "mate" is a paradox.. being that you must not "look" exactly, knowing things will fall into place.. when of course "u are looking" for someone.. I think I had a chance to bring it all up to her earlier today but I let it slide.. :/.. gonna keep trying..

What Girls Said 1

  • try a dating website, there's this free one called okcupid.com, or you could try asking one of flings to be your girlfriend

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