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Dear Uncle Mat 

I’m a teenager living in Florida, and it’s starting to suck more than a Vegas hooker on Friday night. I’m entering my senior year of high school, and I’ve yet to have a serious girlfriend other than a long-distance one who lasted for about two years.

I’m still a virgin, but willing to live with that if I could at least get dates. I can’t understand it. I’m a nice guy and funny, or at least I’m told. I’m not overly nerdy, I know how to have fun, and I’m far from timid. Sure, I like comics and other nerdy stuff, but I’m also an artist. I attend a Magnet High School just so I can major in fine arts. I’m also a writer and musician. I’ve won poetry contests, and I write lyrics for my band for which I sing lead. My band is actually starting to pick up, playing shows and recording tracks.

I’m smart, really creative, and not a bad-looking guy. I’m big, and a bit hairy, but not fat. I’ve actually lost 60 pounds in the last year just so I could be more aesthetically pleasing to women. Long story short, I have all these qualities, I’m not sheltered, I’m not a timid nerd, I’m a good guy, yet I can never get girls to go out with me.

I try, I really do. I just always end up the “friend,” the “brother,” or my personal favorite, “Gay Boyfriend.” Girls like spending time with me, but not in “that way.” Which sucks insanely for me. I’m of Spanish heritage, so I have hormones pouring out of all my orifices besides the obvious one. I have all this energy, all this passion for loving women, and no one willing to give me a chance. People tell me it’s because I’m too mature for the girls in high school, and I should wait for college, or even later. They won’t want the boys who look like women then, they’ll want guys like me. Even if that’s true, it’s messed up. I know plenty of guys like me who can get dates.

I’m nearing my rope’s end. No one around me wants to give me a chance. If I wait and let them come, they don’t. If I strike first, I always seem to miss. I’m not someone to slip into depression, I can always get over my problems, bite the bullet, but I’m so tired of chewing.

As my friends often call me,

This is a Charlie Brown with balls who could sure use some help.

Dear Blue Chuck,

This is rough. I want to tell you that a girlfriend isn’t that important, but it isn’t true. Not for you. If being in a band was the most important thing in the world to you, then it would be, and no one could change that but you. You’re at an important age for determining personal and social values for the different aspects of your life. So humor me, and spend a little more time enjoying all of the cool shit you do and a little less obsessing over girls. In return, I will share the very little I know about getting them.

Being a poet, a musician, and artist only appeals in a romantic and sexual way to a small number of high-school girls. It looks good in the movies, but only about three percent of teenage girls will date or sleep with you because of it. Later, girls realize that this is actually hot as shit, and in your 20s they will totally jump your ass. You could date older women now; boy toys are totally chic.

Always date or try to date women who are smarter than you. Girls who drink and swear are more likely to like an artsy guy. I would suggest you stop looking for them at school. Try hanging out at local coffee shops and all-ages music venues. Be careful. Be sure to take a friend with you — just make sure they know that they are there as a wingman and safety, not a cock block. If you get laid, use a condom. I’ll say that twice. If you get laid, wear a condom. Have fun; high school is almost over, and then life gets better and the women get hotter (unless you turn out gay — then life gets super awesome and women get jobs or something useful.)

Much luck and a little action,

Your Uncle Mat

Uncle Mat answers questions about relationships, sex, pets, and art. Email him at or Your true identity is safe with him.

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