Just Admit it, Jer-Bear

Whatever a normal person’s odds are for finding themselves in harmless-but-awkward-as-hell coincidental situations, my odds are double or triple. It’s a gift of mine — one that I don’t want.

I had been on two dates with a guy named Jeremy, but I wasn’t very excited about him. He was really nice. And I don’t mean he was so insanely nice that that’s what was horrible about him. He seemed like an all-around good guy, had a great job helping others, and owned a condo. He was also from my home state, so we already had a ton in common by virtue of being transplants in Boston.

What made me not as sweet on Jeremy as I should’ve been? My ex. I was not over him. I had signed up for Match.com because my ex was dating already, and I was overtaken by a deep sense of, “if he’s ready, well then so the hell am I!”

Jer-Bear and I were still in negotiations about when and where date number three would be when, on a Thursday evening after a going away party, a few coworkers and I went looking for a bar. We wound up at a spot with live band karaoke. Yup, that’s right, sing karaoke with a live band behind you. Obbbbviously we weren’t leaving anytime soon.

In no time, I spot a nicely dressed guy who — from behind — I decide looks like Jeremy, only hotter. Imagine my surprise when he turned around and was in fact Jeremy. Jeremy in the company of a young, tall blonde woman (much like myself. Clearly someone has a type!).  Achievement unlocked: unknowingly checking out someone you’ve already been on a couple dates with while they’re on a date with someone else.

I laughed off the ridiculous coincidence of it all, because that’s what you do after having more than two decades full of these types of run-ins. I told my coworkers about the current scenario, and surprised most of them by responding “absolutely not,” when they asked, “OMG are you mad that he’s on a date with someone else??” We’d been on two dates. I certainly didn’t consider us exclusive, so why would he? Plus, remember that I wasn’t exactly 100% invested in dating at the time, anyhow.

My plan was to do nothing about being in the same large bar as Jer. Maybe give a little eyebrow raise to say, “oh you’re not seeing things, this is really happening,” if we met gazes. Nothing more, nothing less.  Then my friends and I took to the karaoke stage to sing what I assume was the most beautiful rendition of Sweet Caroline that anybody had ever heard, and once we finished, Jeremy had vanished.  Seconds later my phone started the obnoxious ping ping ping of receiving text messages.


“Looks like you and your friends are having fun.”

“Good song choice.”

“How are you?”

I looked around, spotting Jeremy’s blonde friend over at the bar, but no sign of him. I began typing. “I’m good. Where are you?” but before I was through, a fifth text came:

“Texting from the bathroom.”

Welp, that answers that question. But uhhhhh…what the heck? There were two acceptable routes to choose here (at least in my opinion). 1) say nothing to one another until later when we have a good chuckle. 2) make a small gesture acknowledging one another and then revert to option 1. Nowhere in my mind was there, “leave current date sitting alone to go text other girl from bathroom stall.” Maybe that would’ve sill been on the table if my brain were that of a high schooler? Hard to say.

I messaged him saying a quick, “I’m good, hope you’re having fun,” set my phone to silent, and resumed my awesome evening of dancing, singing, and beer consumption with friends.  He sent a couple other texts during the night, but I chose not to respond until the next morning when he asked a direct question about whether I’d like to get brunch the next day. I said, “That would be fun. How was your date last night?”

Him: “Oh that was just a friend, I wasn’t on a date.”

Me: “hahaha yeah okay. You can admit you were. I’m in no way mad, I’m just teasing you.”

He once again declared that his night out with his female companion wasn’t a date. Was it? Maybe not. It had looked pretty date-y, and if it were a friend wouldn’t you have said “oh hey let me go say hi to my friend B — she’s across the bar,” instead of texting like a weirdo from the bathroom? Maybe not. Maybe I am overly confident in my assumption that he’d been on a date and was needlessly lying.

Regardless, I never did go get brunch with Jer-Bear.  His only purpose now is to serve as an example of my propensity for finding myself in awkward situations.

With love, B!

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