#1: Jessie’s Girl

As a new feature, I’m reliving the stories of my top 5 worst/funniest/best-date-story stories. Here’s the absolute worst date I have ever been on and is simultaneously the best story to tell…drumroll please…#1: Jessie’s Girl!!

Setting: Jalapeno’s Restaurant, Peru, IL, 2008

As many of you can imagine and some of you can attest to, the dating scene in Ottawa is not exactly jumpin’ jumpin’. Unbeknownst to many of you previous to my #5 worst date, I dabbled in the online dating world while living in O-Town, a few weeks on OKCupid, a few on Match. Not much came of the then-modern technology except for a few awkward dates that I immediately wanted to leave right after arriving and a few really great first date stories; in fact, my first ever worst first date story brewed from this initial experiment in online dating. I’d like to divulge said story not only to incite laughter, but to relive the glory days of grand ol’ Ottawa.

Out of the four dates induced from my online dating adventure in Ottawa, two of them were on the same day, a lunch date and a dinner date – about the most scandalous thing I did in LaSalle County. The lunch date drove an electric blue Mustang and was incredibly boring. When I arrived at dinner, the fact that guy #2, Jessie, drove a lime green Mustang should’ve tipped me off to the terrible, horrible, no good, very bad date I was about to embark upon. While Jessie certainly wasn’t a looker (what can I say, there weren’t very many options on OKC back in the day!), I decided to get past this fact and concentrate on the average Mexican food…and the conversation.

Throughout dinner, Jessie continuously rubbed his nose, claiming that “someone must be thinkin’ about me…” Now, I really wish I was more technologically savvy because I’d love to have an audio of this next bit…nearly every time I’d say something, Jessie would exclaim “Whuuuuuuuttt?” Please, right now, say this out loud.

Imagine it:

Me: How’s your dinner?

Him: Whuuuuuutt?

Me: Um, how’s your dinner?

Him: Oh, good. How about you?

Me: Tasty! The margarita is good, too!

Him: Whuuuuuutt?

You catch my drift, right? I wanted to punch something after the first 10 minutes of conversation. Don’t worry, Mom, I didn’t punch anything, though, I did come really close when the conversation turned to what color he wanted to paint his bathroom. My memory is fuzzy here, but he might’ve pulled out color swatches.

After the bill was paid, I was in a rush to hop up, but with puppy dog eyes, Jessie reminded me that “You promised we’d get dinner AND drinks.” Didn’t that margarita count, dammit?

I relented and drove behind him to a nearby bar. Was I delusional? Crazy? Desperate? No! Maybe I just knew that our awesome story didn’t end at Jalapeno’s. At the bar and settled into our seats, our rather mind-numbing conversation continued until…a very special and near-to-my-heart sang came on and I was serenaded. Can you guess the song??

Yes, “Jessie’s Girl” by Rick Springfield!! “The bartender’s playing this for us!” he proclaimed in the lull of the song. For the remainder of the song, he continued to sing…out loud…to me.

Was Punk’d a thing back then? Because I was pretty sure that Ashton Kutcher was about to pop out from under the indoor bacce ball table. My eyes darted from side to side, “Is anyone going to save me?” Apparently, the two other people in the bar didn’t care that the words didn’t make sense coming out of Jessie’s mouth (refresher: “Oh I wish that I had Jessie’s girl…”)

I skedaddled as soon as the last note was sung. I’ve been telling this story for years and years and it never gets old.