Young Man Went West #33: Someone’s Been Checking You Out!

If you’ve been following my blog from the beginning, you may have noticed that Jenn is the first girl I’ve ever really written about. It is not because I had nothing to write about on the subject of dating until now, but rather because none of it was positive. To do so before would have been an exercise in self-pity, most likely devolving into woe-is-me, Nice Guy rants. There is enough of that on the Internet; I thought I’d spare you.

Needless to say, I suck at dating. I hate “the Game.” I mean, give me some face-to-face time with a person and I could pique their interest with witty repertoire and a smile, but that’s not how it works. Nobody gives you that time, you earn it by throwing one-liners and free drinks at any pretty thing on two legs. Eventually, you end up buying a meal for someone who looked better in the dark and sounded smarter before they spoke. I couldn’t operate in that system.

That’s why I signed up for OkCupid, one of those free casual dating site. I figured you would come across as many undesirable people as you would at a bar, but had the added bonus of screening them for potential before wasting your money on their drink. Also, you’d have all the time in the world to figure out what to say.

What I found out was there are a great number of undesirable people on this island, and those who aren’t rarely respond. So many of the profiles I browsed showcased unflattering photos, weird interests, and/or deplorable grammar. Apparently, social networking sites are where sensible syntax and necessary punctuation go to die. So my account, like my real world love life, lay dormant for a long while.

That is, until I came back from my road trip. It were as though the life points I racked up by being awesome and exploring the country returned with me to Honolulu and spread out into my normal life. I got my place back with lower rent, I got my job back with awesome new coworkers, and I found an e-mail waiting for me that, little did I know, would change my life.

“Hey Anthony, someone’s been checking you out!”

That’s the subject line OkCupid uses in the e-mails they send you to inform you that another user was browsing your profile. I’d get those every once in a while, but the links often brought me to those aforementioned profiles. This one, however, this very first one I received upon returning to Honolulu linked me to the profile of a recent college graduate with modest photos, a keen interest in arts and social issues, and impeccable grammar. I figured I’d send her a message.

The messages I’d previously send to other users were often long, witty, over-edited speeches about common interests and our potential for compatibility. I rarely received replies. So, in a jaded, carefree manner, I kept it short and to the point. You’re interesting. Let me buy you dinner. And wouldn’t you know it? That worked. This girl replied, first asking to know more about me, then later asking where we should eat. I had only just started back up at Bubba Gump’s, but I figured I had enough dough for one date.

Now, as I mentioned, I was in a somewhat jaded state about dating at this point. I had always looked for a relationship and got nowhere. I figured, with this Internet girl, I’d just enjoy myself and expect nothing. I wasn’t even expecting her to be all that attractive; few of her photos revealed her body and all of them obscured her face somehow, save for a great smile. Apparently, that–and her interest in foreign films–was enough for me.

So there I sat in a small wine and tapas place I’d never heard of but lived close to, looking forward to promising conversations with an average looking girl. Suddenly, a stunningly-dressed, petite young woman with eyes as gorgeous as the smile I recognized approached my table.

“Anthony?” she asked.

More like Jackpot Winner, I thought.

She sat down and conversation started to flow naturally. Still, I stayed within my self-set guidelines:

  • Ask her questions about herself. Show interest, sincerely or otherwise.
  • Smile and make eye contact.
  • Don’t talk about myself too much. If she asks, answer completely and briefly, then turn it back to her.
  • Mention, but don’t talk in great length about: my road trip, why I moved to Honolulu, studying abroad, how much I love my family, and how I was a camp counselor for young children with juvenile arthritis the past three summers. Spark the interest, leave it alone, then let her ask.
  • If it fits in the conversation, also offhandedly mention volunteering at an orphanage in Mexico.
  • Forget that last guideline; that’s too much. Way too much.

My guidelines seemed to work. I was having a fun time getting to know her and I didn’t feel like I was babbling on too much, like I tend to do. We talked about college, film, future plans. All the normal things. We also talked about OkCupid and how we each used it. Unlike me, who signed up over a year prior yet reaped no benefits, she signed up only a few days before and was already on her first date. She consciously chose unflattering photos to ward off shallow meatheads, and wrote about her senior thesis in length on her profile wall to ward off idiots. The photos didn’t faze me and the senior thesis was a turn on. Things were going well. . .

Until the check arrived.

I guess I wasn’t used to higher end places because I figured a fifty-dollar bill would cover it, backed up by my debit card. Little did I know, three glasses of wine, my escargot, and whatever meal she got added up to nearly $80. Secretly shocked, I told him to use the cash first and put the rest on my card. Why did I only bring a $50?!

I continued on with our conversation, but the waiter came back with a look on his face that carried no good news. The card was declined. No worries, I thought, I’ll just try the debit card from my mainland account. However, my finger found emptiness in the slot in my wallet where that card should be. I riffled through my wallet several times before thinking, “Look, I have literally have no more money to give and I’m sure she does. Why shouldn’t she pay for part of it? I mean, we both ate and drank, and this is the 21st Century!”

Untimely progressive ideals clouded the spot in my brain where shame should have been as I asked her with feigned embarrassment to cover the rest. Without hesitation nor the slight inclination of disapproval, she did. Covering the rest of the check didn’t bother her at all, or at least she didn’t let on that it did. That was when I was hooked.

We carried on with the rest of the evening as though I didn’t just perform the biggest date faux pas, and within the next few days, she had agreed to a second date.

Meeting online and splitting checks? A new age of dating had emerged, and I was top dog.

Our first photo together, taken a few weeks after that awesome first date.


1 Comment

Filed under YMWW Blog

One response to “Young Man Went West #33: Someone’s Been Checking You Out!

  1. Anonymous

    Dating tips for the 21st century man. Thank you, sir.

    You and “Jenn” look very cute together. I look forward to the next chapter of this modern day love story.

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