Most Awkward First Dates

In my dating life, there have been a number of unfortunate moments. And I may or may not have once inadvertently forced some wait staff to stay long past their shifts were over because no one wanted to tell the crying girl at table 7 the restaurant was closed, but since I decided to limit this post to first dates, here you have it:

1.     The World’s Shortest Date

Shortly after I graduated college, I met a man who was out with some guy friends of mine. He was in D.C. to interview for a job on the Hill. He asked for my number so he could call me when he moved to town. I gave it to him thinking, “I’m sure I’ll hear from this one.”

But, strangely enough, three weeks later while I was shopping in the Safeway, my phone rang. “Laurel, it’s Joe.”

Luckily, he was kind enough to give me some context clues because I had no idea who Joe was by then.

“Anyway, I got that job,” he said, “so I was thinking I could take you to dinner once I got up there.”

“Sounds good to me,” I said, and we made plans for an upcoming Thursday.

Joe came to pick me up, and we decided to walk to a restaurant in my neighborhood for dinner. We ate, talked about what might have happened to Chandra Levy, and he walked me home. From doorstep to doorstep, it took all of 45 minutes.

“How about I give you a call this weekend when I know what I’m up to?”

“Sure,” I said, knowing full well that phone call would never come.

Maybe the real me didn’t match up to the memory, but I’m not sure what I did to warrant holding onto my phone number for three weeks only to end up being someone Joe didn’t even want to spend an hour with.

2.     We Shouldn’t Have Talked About Music

Date #2, who we’ll call Dan, was an office fix-up. Now, in my opinion there is little more awkward than the office fix-up. It’s pretty hard to say “no” when Sue from HR or Tammy from accounting wants you to go out with their adorable nephew or wonderful son when they know you’re single. There’s never a good excuse (especially if you did not create a pretend boyfriend on day 1 of the job), and you usually just have to go. Also, if it goes wrong, as it usually will, you quickly go from being the cutest girl in the office to the evil heart breaker who thinks she’s too good for everyone.

While Dan was watching me eat nachos on our date (he couldn’t have so much food because of a recent surgery), I turned to the gold standard of dating small talk – music. Since “With or Without You” happened to be playing overhead, I said, “I really like U2.”

“What?” he said.

“I really like U2.” I even pointed upwards thinking he would somehow catch the music playing in the background even though he couldn’t hear me, and I was sitting right next to him.

There was a long pause.

“Oh, uh, I like you, too,” he said.

Then an even longer silence set in – partly because I was embarrassed and partly because I really didn’t know where to go from there. I also didn't like him that much, so half an hour into our "relationship," it was already based on a lie.

When he walked me to my car after I made up an excuse to go home before 10, I literally said, “Good luck with everything” and gave him the double pistol shoot with my hands to make sure there was plenty of space between us as I got into the car.

If there’s ever a biopic of my life, I’m hoping that moment of social genius doesn’t make the cut.

3.     There is little shame like the shame of being judged at the Olive Garden

My first date was a double date with another couple. While I’m sure the other couple was brought along to make the situation less uncomfortable and awkward for me and my date, well, we all know what they say about the best-laid plans.

The couple my date and I were doubling with had recently gone through a break up due to some cheating but had gotten back together.

After our 45-minute wait at the Olive Garden, we were seated. We ordered our meals. Things seemed to be going well. Then, the trouble began.

I’m not sure how the cheating came back up, but as the waitress was delivering our food, my friend said, “You know Mike, if you aren’t happy with what you had, you’re welcome to send it back for something else.”

“No, I’m perfectly happy with what I have,” he said.

“Well, you certainly don’t act like it. Maybe you’d like something newer and more interesting.”

“No, no. I like what I have.”

This conversation went on much longer, but my date and I were able to finally signal to the bewildered waitress that she could deliver the food and walk away. (The metaphor was not nearly as clear to her, and she kept offering to ask for changes in the kitchen.)

The fight culminated when my friend slapped her date. In the middle of Olive Garden.

You’d think it’s impossible to bring everyone to a dead halt in a chain restaurant, but just like that, you learn that it isn’t all that hard after all. Everyone was looking at our table. The room was silent.

My date and I spent the rest of our meal staring into our plates of spaghetti. On the ride home, my friend and her date “made up” in the back seat for most of the trip. Needless to say, we didn't go out again.

Not to point any fingers, but this may be one of the reasons it took me about 15 years to get a better handle on the dating thing.