Dear Uncle Mat

I am a guy heading into my junior year of high school. I consider myself to be happy, although at times I tend to reflect on the fact that I haven’t been involved in an actual relationship. Although I realize the joy I derive from my experience in high school isn’t entirely dependent on being in a relationship I don’t think I’m a bitch for wanting to find a decent-looking girl I have something in common with. I’m not necessarily gorgeous but I’m good-looking and have gotten better-looking over the summer (courtesy of weight-lifting, running, and tanning), although the main blow my social life endures is my low self esteem and subsequent anxiety and awkward behavior. Usually when I’m on a date I can engage a girl in conversation, although it becomes evident to both of us that the bulk of our conversation is fueled by bullshit and her interest in me quickly deflates. If I’m lucky enough to wind up on a second date, the conversations and time I spend with whatserface is a little more intimate and I usually get a kiss out of the experience (not just a peck either as far as the tongue is concerned) but it’s probably pretty bad on my part or completely overshadowed by overly cautious behavior considering whatserface cuts it off after that. I realize my dilemma isn’t uncommon, however it still seems unanswered and I’d like to at least experience a healthy relationship before I graduate, so please reply.

— Basket Case 

Dear Basket Case,

Have you ever seen a John Hughes film? High school is filled with awkward dates, sloppy kisses, disappointment, and enough other small personal tragedies that you should be really thankful at this point there is such a thing as masturbation. I want you to remember that you and girls will most likely be cooler, hotter, and a lot more fun in about five years or so.

Get a hobby. This adds depth to your personality and hopefully some confidence. Just avoid activities that can be done in your basement with five other guys who call themselves druids and a handful of dice or picture cards, and that replace the life you already don’t have. Skateboarding, sports, art, music (playing or listening), or even ornithology can be cool if you know your shit.

Be confident, not cocky. Apply a “who cares” attitude to your social status, not your date. Avoid being a rank-and-file dude constantly dogging the girls for dates and action. Think of the girls as individuals and peers, not objectives. The term “whatserface” suggests a bit of overcompensation for your insecurities. Making friends with a few girls might help you out. Regular interaction with women will demystify them and break down the gender barrier. When you do ask out a girl, plan dates with activities or built-in interaction, such as bowling, skating, or a live-music show. This helps take the focus off the two of you and offers neutral conversation topics (not just about you or her).

Learning how to kiss is especially tough if you believe you’re bad at it. Think of it as a conversation you are having with the girl. It should be an experience of both invention and discovery. Every girl will kiss differently, and though you will have your own style, it is nice to begin to match and meet her. Be complementary in your approach, not overly aggressive — you are not pillaging her mouth with your tongue. I most often hear the complaint men kiss too sloppily and lack physical control over their tongues. If you’re not sure you understand what this means, make out with another dude.

The last thing to remember is that no matter what she says or how she acts, the girl is also feeling awkward and unsure during the date. This is the core of the disease known as being a teenager. Everyone is overly self-aware, insecure about their looks, personality, and brains, constantly horny, and deathly afraid of any of this being discovered by anyone else in the containment camps we refer to as high schools. Have fun, and the rest will fall into place. A few good dates and your dreams of high-school romance will be coming true before you know it.

Much luck and love,

Your Uncle Mat

Uncle Mat answers questions about relationships, sex, pets, and art. Email him at [email protected],, or check out the Dear Uncle Mat Page on Facebook. Your true identity is safe with him.

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