"Dude! I don't talk to her about computers!"
My attention was immediately unriveted from my book and tea. I was at my favorite new lunch nook, The Tea Garden, waiting for my ramen, when the nerdy Asian boys brought their socially challenged friend to lunch, for what I can assume is the male equivalent of the girl's confab. I realized he was in trouble immediately because one- he had no inside voice and two- he was berating his friend for his "useless advice."
I quickly gathered that the boy was suffering from a bad case of "the friend zone." He had been hanging out with this girl since October and wanted to change the status of his relationship from friends to oooga chahka ooga oooga...more than friends. "I mean, we even spent hours the other night cuddling!" he proclaimed to the restaurant at large.
While his friends used inside voices, and I didn't hear what they were saying, I gather one was advising him to play it cool and wait for her to come to him, and the other was encouraging him to go for it. Then they were coming up with strategies for him to create the perfect date where he could express his feelings, planning expensive dinners or going to exotic locations.
I so badly wanted to get up from my chair and sit down with those boys and tell them what I have learned from both study and experience. Oh, sweety! Just tell her you like her and see if she likes you back. No games. Surgical, get in, get out, don't leave any sponges inside.
First, gentlemen, if a girl is cuddling with you, she probably likes you. If she is spending more than one night a week with you of her own free will, she probably likes you. If she touches you affectionately, hugs you, knows your likes and dislikes, she probably likes you. If you wait for her to come to you, you may be waiting for a long time. Even if a girl is in deep smit, she will most likely fear rejection and want the guy to make the first move.
Now, granted it took me a couple of months of that post hang out "GAAAAAAAAHHHH!!!!" feeling to get the gumption to text my current boyfriend to figure out if we were dating or just hanging out. And guess what? Having that conversation, (because no matter how it starts, it will lead to a conversation) didn't cause either of us to spontaneously combust, get attacked by zombies, or lose our comic-con passes. But that is the first time in the 14 years that I've been attempting to date that I did anything close to making the first move.
Second, sir, fortune favors the brave. Conversely, weak-spined cowards rarely get laid. I once read a story where a guy met a woman in the New York Blackout, and was so taken with her that he tracked her down afterwards. Women hear these anecdotes daily. If you can't sack up enough to go, "Um, I think you're really cute/ awesome/ kickass and I think we should try going on a date to see where this goes.", then you are screwed. And not the type of screwing which requires protection.
So here's my advice: go for it. The worst thing that could happen is that she's not actually into you...well, I guess the really worst thing would be if Leonard Nimoy and William Shatner were at two different conventions in the same town on the same day, at the same time. Or that Wil Wheaton came to your town and started dating your sister. The upside is that if she's been hanging out with you socially for any extended period, she knows you are socially ill-equipped, but celebrates your diversity.
If you are unsure how to broach the subject, I personally would advise against taking your friend to a really unusual or far-away place to discuss your feelings to avoid awkward long silences. I would recommend that you hang out as usual, and discuss your feelings in a private setting, such as your apartment when your roommates have been told to get out.
Lastly, if you are unsure if she likes you back, take advantage of the fact that this is the information age. Be a weaselly bastard and ask a mutual girlfriend if they think your paramour has feelings for you, or would at least be interested in dating you. There is something flattering and attractive about someone telling you they think you are the greatest thing since cylon toast.
So, in closing, boys, don't overcomplicate or overcompensate. Take a chance if you feel you have a shot. Last, sometimes we are wrong. Sometimes we get rejected. It rounds us as people and gives us experience. Be nice and be yourself. It'll be OK this time or the next time, if this time around ends up sucking more than Wil Wheaton as Wesley Crusher.
