Dateless in Philadelphia

In the movie Never Been Kissed, starring Drew Barrymore, she returns to her high school, about 10 years later, as an imbedded undercover journalist to report on what really goes on in high school. She begins by reliving her miserable, outcast-like high school years. With the help of her brother, she ironically becomes a part of the "popular" crowd and even is awarded prom queen honors towards the end of the movie. The most important aspect of this film though is that Barrymore's character, has never been kissed. As fairy tale endings go, she ends up falling in love and getting that first kiss she has always dreamed of by the end of the movie.

So, my life somewhat parallels this movie, in that I have never been taken out on anything that would qualify as a date, in my mind anyway. Similar to Barrymore in this movie, I was awkward and shy most of my life. The only "boyfriend" I had as a teenager lasted for a few months in 9th grade--if that even counts. In high school, I was still somewhat a tomboy, just beginning to embrace femininity (whatever that means, lol), so most of the guys I was interested in, became my friends and once you are in friend territory it is very hard to get out.

OK, so maybe I wasn't completely dateless. My junior year of high school, my best friend set me up with one of her male friends, who was definitely more interested in her than me. I went on the date anyway. It was an awkward time. We saw this movie, Zoolander, that wasn't really funny and he did not say much to me the whole night. I had to do most of the talking ( imagine that!). It was obvious he wasn't interested and neither was I. He was a nice guy but kinda boring. That was our first and last date. That was my first date and the last one I can remember. I've been out with guy friends on numerous occassions since then, but none of those were dates in my mind. I would think there would have to be some kind of mutual interest in order for these to qualify as a date.~

So, how has my love life existed without dates? Shouldn't they be coexistant? I feel like I'm missing out on something.

"If a guy really likes you he will take you out, " my Dad first told me and my sister on a road trip to Brown University, my senior year. We were analyzing the fool that had just broken my sister's heart. She fell in love with him and settled for the way he treated her. He never wanted to take her anywhere...he just kept her under wraps. So my dad's rubrick for telling if a guy is interested, has stayed with me and has yet to have been fulfilled by any of my "love interests." It's kind of sad. I have this friend who probably averages about three dates a week and it's stressing her out. I would like to have half of her problem.

I am not going to go into all of the factors that have stopped me from dating, (there are many),but all I want to know is. can I get a break? Sheesh. Can I enjoy art, music, or food with someone I enjoy just as much? Someone who doesn't mind being seen with me, preferably does not already have a girlfriend, and with whom there is a genuine mutual interest. Is that too much to ask?