Mirth

Hello everyone. Couldn't think of a fitting title, but this thread is about my current life/female dilemma.

I'm 23 years old and have never had a girlfriend (Okay, I did in 8th grade, a girl asked me out and she dumped me the next day; I think it was a joke/dare). In middle school, I was a pretty popular guy, but in High school, I just stopped talking to pretty much everybody; I suppose it was because I started looking at myself as I "thought" others saw me, and I guess that's how I felt, and how I still feel to this day, leading me to a shyness that has taken over my life.

The negatives, oh the negatives. I don't really feel that great about my physical attributes. I'm 5'5 and although "I" don't mind being short, I feel that guys who are average height or greater just have a better chance of getting girlfriends, and when I see what women post about their ideal guy on myspace or message boards and things like that, they prefer guys taller than me, so I have this mindset that it's confirmed that my chances are slimmer. It's not just the height though; I know for a fact that I don't have an attractive face. On top of that, I have very "boyish" features: I don't have hair on my chest, I can't grow a beard -- just stupid pubes on my chin -- and I'm ALWAYS mistaken for being 16 years old. 9.5 out of 10 people would not guess I'm a day over 20. With that being said, how can I approach a girl and let her know right off the bat that I'm not some High-School Freshman hitting on her?

A little bit of a side note of me actually trying to change and getting my ass handed to me: I was living on my own in a different town, but when I visited my hometown I was introduced to my brother's girlfriend's step-sister. Didn't think much of her at the time, until we hung out a few times, and my brother texted me saying that "she likes you". I said, "cool". When I visited my hometown, I hung out with her a few times, and I started to like her. I wasn't doing great in the college I was going to, was barely making the rent, and I'll be honest, was very interested in her enough to move back home, where I can continue college at a better place and possibly date her. I went out mini-golfing with her one night, and she seemed really weird about it. Later my brother texted me asking if it was a date or friendship and I jokingly said, "either is fine with me ; )" because really -- I don't know anything about dating or how to initiate one so I was lost -- and he told me that he'd "hate to break the news, but she just wants to be friends. She was talking to her sister about telling you that tonight, but she just couldn't do it" So it was kinda my first major pain in my heart, and without thinking, I private messaged her on myspace telling her how I felt about her, and asked her if there was ever a time that she liked me. She replied and said it's not my fault (God only knows what that means...), and didn't really answer the question about her ever liking me. It just hurt(s) so badly that I don't know if I want to feel that way again, but I know if I ever want a girlfriend I have to take that risk.

The positives... Well, I'm doing really good in school, I have wonderful and caring parents, I'm not in debt like most college students and am really good with handling my money, I'm joined a band a month ago, and I have a good part-time job working for my parents. Even though I have all of that, I just feel that I'm missing a huge chunk of part of my life; a girl. I feel like, I don't know, it's starting to get too late for me when it comes to a girlfriend; I've never kissed a girl, don't know what breasts feel like, and I'm still a virgin of course. I don't know how I'm going to tell her that she's my first girlfriend, let alone the other stuff. I feel like a 40 year old guy who wants to start a career in the NFL or something; it's just too late...

On top of that, I really don't have any social outlets. I don't life the bar scene because I very rarely drink and I don't want to end up with a girl who's a regular customer at the bar. My job consists of fixing cars for all the old people in this old people town; rarely does anyone under 30 come to our car shop to get work done. And out of the University and Community college I go to, the major I'm in at the Uni is like, 100% male students, and the community college I have 1 class per semester usually, and last semester the girl I was really interested in... I couldn't even talk to her without shying up too much. =\

So anyways, I really don't know what to do. I'm back in this small, lifeless, geriatric town that has no entertainment and ALL of my friends have moved, so I don't even have them for comfort anymore. I want a wife and kid(s) someday, but at the current rate I'm going, I'm terrified to think that it may never happen for me... I don't know how to start pretending to feel good about my looks. I don't know how to stop being shy when I care too much about how others perceive me and don't want to say anything stupid. I don't know how to get people to stop thinking I'm 16 without me telling them. People have told me in the past, "Just talk to any random girl and blah-blah-blah", but I just don't have it in me to make that drastic of a change; there's got to be some sort baby-steps that will help me change, but I don't know what they can be.

Thanks for reading, and any advice would be greatly appreciated.