My Worst Dating Experience

I was nineteen.  My first long-term relationship (officially nine months, unofficially a year-and-a-half) had recently ended, and I was finally starting to come out of the post-breakup depression.  I was on a weekend retreat with my college’s Christian Fellowship, surrounded by a few hundred Christians, half of them female, many singles.  And I was determined to ask one of them out.

(The more experienced among you, given this set of data, are probably already wincing.  It’s a bad combo of events, unlikely to end well.)

I ended up asking out a woman who was on the same charter bus as me (her chapter was from a neighboring college).  We had struck up a conversation, exchanged some small talk and some movie critiques, and when I randomly asked her out I was really rather surprised she said yes.

I went with the standard (read: boring) option, dinner and a movie.  She wanted to see Punch-Drunk Love, but I’m not an Adam Sandler fan, so I went with the only other not-action-flick movie that was playing, My Big Fat Greek Wedding.  (Protip: never take a first date to a wedding movie.  It’s more than awkward.)  I was late picking her up because I couldn’t find my way around her campus (lots of one-way streets).

I remember that the conversation kept dying.  Like a determined ER doc with a defribulator, I kept trying to resurrect it by asking random icebreaker questions (which works great for a youth group, not so much for a first date).  “What’s your favorite breakfast cereal?”  “What’s your favorite color?”

I think I brought up my ex-girlfriend once or twice.  (Cringe.)

The conversation was not improved post-movie, when I kept babbling about how the Greek family in MBFGW reminded me of my Italian side, and how the movie was basically what had happened to my parents only with less of a resolution.

I dropped her off relatively early, and was too stupid (and desperate) to quite realize how painful this event had been for both of us.  A day later I ignored the two-day rule and called her to ask her out again, ended up leaving  a message with her roommate.  A day after that, having not gotten a reply (and not taking the hint), I emailed her.  (Can you say, “Desperation?”)  She eventually emailed me back to basically say that she had a boyfriend but thank you for the lovely evening.  (*blink*)

And that was that.

Fortunately, I did not ask anyone else out again until A) I was fully over my previous girlfriend, and B) my date-taking skills had improved.  Because too many cringeworthy dates like that might have convinced me to go monk.

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