If you’re a female, you have no doubt dreamed of what it must be like dating me. Well, I’ll tell you: it’s awkward and painful for all parties involved.
Case in point: my brief relationship in 1998 with Adrienne. Adrienne and I met at a pop-punk concert at a roller rink in North Jersey. I was a junior in college. She was in her second year at art school. We were introduced at the show by our mutual friend Andy. We talked for about 45-minutes. During this conversation I learned that Adrienne was: A) Beautiful, B) Smart and C) Funny. Naturally, despite all contrary evidence, I thought that there was no way a girl this awesome could be interested in me. Thus, I neglected to get her phone number.
Alas, our relationship was not yet doomed. Weeks later, Andy and I called her via 3-way, a phone calling system largely used by middle school students. We made arrangements to go out on a date that weekend.
This was the first real date in my life. I had been on “dates” before, but they never technically fell under the traditional rules of courting. This did. This made me incredibly nervous. About an hour before I arrived to her house, I vomited out of nervousness.
Nevertheless, the date continued. It started off well, with us getting coffee and having a good time. It then soon turned awful, as I drove around aimlessly and painfully, and talked even more aimlessly and more painfully.
Along the way I said the following comment to her:
“I will become a vegetarian for you.”
Soon after this pronouncement, we parked at Verona Lake, one of the area’s premier make-out spots. I put on a cassette tape entitled “The Best of Bill Cosby.” After about two minutes of listening to The Cos, I made my move. I leaned over the emergency break and fell over Adrienne, somehow kissing her on the cheek in the process. Immediately afterward, she asked me to take her home.
She stopped returning my calls after that.
I’ve had a lot of painful and awkward moments in my life. This ranks really high on the list. At this time in my life, I really lonely and constantly beat myself up over not having a girlfriend. And then, finally, when a girl I liked a lot was interested in me… I completely blew it due to my social ineptness. Dealing with the heartbreak of rejection is bad enough when a person simply doesn’t feel the same way about you that you feel about them. But dealing with the heartbreak of rejection because of your own retardation is a lot worse.
To this day, Adrienne ranks as #4 on my High Fidelity list of all-time biggest heartbreaks.
Luckily, due to the magic of Facebook, Adrienne and I recently befriended each other. She agreed to be interviewed about the experience of dating me roughly ten years ago. Here is the transcript of our exchange:
GREGG: We met at a Weston concert at a roller rink in Wayne, NJ. What initially drew you to me? What were your first impressions of me? When, after 45 minutes of conversation, I failed to ask for your phone number, what did you think?
(The reason: I was completely intimidated by you. I thought for sure your possible interest in me was a cruel joke being played on me by an unknown nemesis. I didn't exactly have a lot of confidence in myself at the time.)
ADRIENNE: Do you hate me for not remembering this until you mentioned it? I love that this happened at a roller rink. How much more awkward teen setting can you get? Ok, so I think I was initially drawn to you because you were a new kid on the block. You didn’t attend my high school, so that made you mysterious and interesting. And I thought you were cute! I don’t remember too much about our conversation, but I remember that I did like talking to you and I thought you were funny, and you had good local band knowledge, which were two things I really liked in a man at the time.
I can’t believe you were intimidated by me! We were in a roller rink!! I vaguely remember being disappointed that you didn’t get my number, but I knew we had a connection through Andy, so it didn’t worry me too much.
We finally went on our date. What were your earliest impressions of me? What were your thoughts going into the date?
(I vomited an hour before hand. This was the third date I had ever been on in my life, the first with someone I really liked a lot. I was really nervous, obviously.)
This is funny, I cannot believe you threw up! I don’t really remember the beginning of the date, it’s the end that stuck out in my mind.
After we got coffee, I started rambling while driving around like a complete and total maniac. I, at one point, said the following: "I will become a vegetarian for you." What were your thoughts when I said this borderline pathological line?
Again, this is hilarious, but I don’t really remember it. At the time, it probably sounded good to me, since I was really into it. If we actually continued to date, you would be happy to find that I reverted to meat eating not too long after.
Finally, after a loooooong night of sad, aimless driving, I brought you to a popular make-out spot in Verona, NJ. My move was to put on a Best of Bill Cosby cassette tape. Then, we sat in long, painful silence. What were your thoughts during the silence? Then, finally, I unsuccessfully tried to make out with you. What were your thoughts on this?
This is the part that I remember most vividly. I actually started to become frightened. Hahahaha, true! I was very worried that you had kidnapped me. I didn’t know how to tell you to take me home, and I guess I thought that if I stopped talking, you would get bored of me, and decide it was time to get rid of me. When you tried to make out with me, I thought it was really poorly timed, since I was already extremely uncomfortable, and I thought visibly so. But, it’s kind of funny, because part of why I didn’t want to make out with you was because I was so inexperienced myself. I was afraid I’d do it wrong.
When and why exactly did you lose interest in me? When I made one, final desperate attempt to call you, and I said something like "I am so crazy about you," what were you thinking?
Haha, oh man. I only vaguely remember this as well. Although I do remember an awkward conversation with Andy, where I said, “How about your friend Gregg that you tried to set me up with?”, trying to get him to trash you with me. And his response was all serious, “What, he’s a nice guy.” That exchange made me feel like a conceited cunt. Hahaha.
Out of my High Fidelity Top 10 heartbreaks, you rank in at #4, between Staci and Jen H. How do you feel to have earned such an illustrious ranking?
(You rank that high because of nothing you did. It was solely because I believe I completely blew it. I got it in my head that you were way out of my league, despite your possible interest in me. I had absolutely no confidence in myself at the time. I tried to be somebody different than I was, which is what I assumed you wanted. The ranking is because I kicked myself afterward for being such a weirdo about the whole thing. Years later, I put it in perspective. I was really lucky to go out on a date with you, and if I had more confidence in myself at the time I probably could have had a second. And that gave me the self-confidence I needed to be more of an adult about the whole dating thing. And then a little while after I figured that out I met my wife.)
Wow, I think you are right, if you had more confidence, things might have been different. But, keep in mind, I lacked confidence as well, making it that much more difficult for things to ever work. My ego is bursting through the ceiling being put on a list like that. I’m surprised you never tried to contact me again if you felt so strongly.
Gregg Gethard is a Philadelphia-based comedian and host of the monthly sketch/monologue show BEDTIME STORIES