Guaranteed Trump

One of the prompts on the list of topics I’ve given my writing students for journals this semester is the story of your worst date.  I’ve been writing along with them, and this one was too fun not to post here also.

I have had so many bad dates that it’s truly difficult to pick a worst.  I think my problem is that because I’m so accepting, people tend to let their freak flags fly when they’re around me.

Now, before I blast anyone, I need to make clear my philosophy on this issue.  I don’t think any of the bad dates I’ve had are bad people; they were just bad fits at that particular moment.  People change.  Different people bring out different features of others’ personalities.  So the guy who’s a jerk to me could turn around and be Mr. Perfect McDreamyson for someone else tomorrow.  There is no judgment in this story. . . just pure entertainment (that was not at all entertaining at the time).

Let’s call him Crying Boy.

Crying Boy wanted to go on our first date on his birthday.  I challenged this repeatedly.  “Are you sure you want to go out on your birthday?  Wouldn’t you rather be with friends or family?”

“No,” he insisted, “I will have already celebrated with everyone before that.  I really don’t have any plans.”

So I agreed.  Note to self:  Don’t agree to things that contradict what you so often refer to as your better judgment.

Dinner was fine.  We had Indian food at one of my favorite restaurants.  I bought, of course, because what kind of jerk makes someone else pay for dinner on his birthday?  Then I insisted that we go get ice cream cake.  It was, after all, his birthday.  See – I’m not the kind of person to let other people go uncelebrated.  I think people deserve to feel celebrated on their birthdays.  Note to self:  People deserve to feel celebrated by those who know them well enough to celebrate them.

Half-way through ice cream cake, my date said, “EB, I really like you a lot.  I can’t believe I’m feeling so sure about you already, but I’m definitely sure.  You’re it.”  And when I didn’t immediately respond in kind, he burst into tears.

No, really.  I mean burst into tears—as in uncontrollable sobbing that includes not only the expected eye leakage but also chest heaving, bottom lip quivering, full on bawling.  And this bawling continued, interrupted only by intense conversation about a recent break-up, his family’s passion for religion, his love of his mother and sisters, and other strange first-date chatter.

It continued. 

It continued for six hours!

Why, you may wonder, did I not stop him?  At some point, I should’ve said what I was really thinking:  “Dude – you’re freaking me out.  You’re unstable, and the relief I feel when you finally leave I’m imagining will be something close to the relief someone feels after a large piece of unchewed beef has been lodged in her throat to be released only by a kind do-gooder delivering the Heimlich.”  Why didn’t I say that?

Well, there are times—probably more times than I’d like to admit—that my discomfort at the idea of hurting someone else’s feelings is far greater than whatever discomfort I happen to be enduring.  This is not a quality I’m proud of.  It’s definitely not something to be applauded or emulated.  But it is me, and the sheer number of bad dates I had to choose from is proof of the verity of that statement.


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