Would You Care To Join Me For An Unbelievably Awkward Dinner Sometime?

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Would You Care To Join Me For An Unbelievably Awkward Dinner Sometime?

Hey, Julie, it's Mike Toomey. You remember me, right? We met at Kevin's party last weekend. That was some party, wasn't it? I had a really great time. And it was definitely cool talking to you. Anyway, I know this may seem a little out of the blue, but I was wondering if maybe you'd be interested in joining me for an unbelievably awkward dinner sometime.

If you're game, I could call you this week to make arrangements. I'll spend a few minutes nervously rehashing this conversation before suggesting a not-very-good restaurant. Then I'll establish our lack of chemistry with several minutes of conversation-extending small talk that feels forced and strangely businesslike.

Your fears about me will be confirmed when I arrive for our date. Even though we'll decide in our brief, halting phone conversation to keep things casual, I'll show up with a dozen long-stem roses and be oddly overdressed. I'll comment on your outfit, calling it "slimming" or "flattering" or some other compliment that comes off like an insult. How does that sound for an inauspicious start to the evening?

We'll then embark on the interminable ride to the restaurant. Trying to break up the long, painful stretches of silence, I'll ask you a series of forced questions, such as what you look for in a guy and how long your longest relationship was. Fearful that you find me boring, I'll try to spice things up by asking you to name the craziest place you've ever done it. And I will actually refer to sex as "doing it," which will turn you off immeasurably.

At the restaurant, the discomfort will deepen. Our only relief will come from the all-too-infrequent interruptions by our waiter delivering more breadsticks. When the house fiddler comes to our table, I will make the ill-advised decision to slip him $5 to play "Moon River," thinking it might somehow create instant romance. While he plays, you'll stare down at your plate and fidget with your silverware until the song is done, trying to avoid any eye contact with me, lest I think my clumsy attempt to woo you has been a success.

As the evening progresses, the conversation will become more and more stilted. I will talk about TV shows and movies in which you have no interest. We will desperately cling to Kevin as a topic of conversation, since he is our only mutual friend. All the while, we will both be painfully aware that we are using Kevin as a conversational life raft.

After deciding to skip dessert, I will drive you home. After pulling into your driveway, I will turn off the engine and say, "Well, I had a nice time." For an agonizingly long moment, I will just sit there as you tremble in fear that I am summoning the courage to go for a goodnight kiss rather than a hug. I will kiss you on your cheek, but close enough to your mouth that you will turn your head to ensure that there is no contact between our mouths. I will then say, "Well, maybe we can do this again." You will reply "Maybe," trying as politely as possible to make it clear that you have no interest in ever seeing me again.

So, are you free Saturday? I know this great Italian place, not too expensive.


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