Awkward Moments in Dating: The Ex-Boyfriend

(image via wikimedia)

This date had several warning signs before it even started.  The first was that we’d met at a football-watching party at a sports bar (we were fans of the same team but hadn’t previously known each other).  The second was that she had been drinking when we met.  The third was that she was obsessed with Garth Brooks.

Keep in mind, this date happened in 1991, before Garth Brooks was a household name.  I didn’t like country music, so I had no frame of reference when she first mentioned him.  I usually can’t stand drunk women, but she seemed to handle liquor pretty well (another warning sign) and understood my sense of humor.  Most people take me literally all the time, so when a nice-looking drunk chick understood my humor and laughed appropriately (she didn’t laugh like a drunk), I blindly hoped she would understand my humor when she was sober, and I asked her out.

Back then, you had to write down phone numbers (or memorize them), and women would often give guys fake numbers (usually to a Pizza Hut or Dominoes) and I had all those local pizza place phone numbers memorized.  Asking her out wasn’t awkward (that was a good sign), and I didn’t recognize the phone number she gave me.  At the end of the party, she left with a friend who hadn’t had much to drink, and she reminded me to call her.  I didn’t walk her out because I didn’t want to seem overly eager.

I called three days later (that was supposedly the number of days that was appropriate in the 90’s), and she answered before the machine picked up.  Even though I’d made an outline for our possible conversation, I didn’t need it.  She asked me a bunch of stuff, and she seemed to like my answers, and we set a date for the upcoming Saturday.  Dinner and a movie.

Yeah, I know that sounds lame, but that’s what she wanted.  There was a movie she wanted to see and a restaurant she wanted to go to.  As long as we stayed out of country bars, I figured things would work out okay.

I showed up on a Saturday night at her apartment, and she held my hand as she led me in.  She maintained some eye contact but allowed me plenty of time to check out her cleavage as she showed me around her place.  I’m not the kind of writer who describes cleavage, but hers was pretty good.  Plus, she kept a really clean apartment.  I had dated a slob before, and that had caused issues (that’s for another “Awkward Moments in Dating” episode).  She suggested a Mexican restaurant that I’d never heard of, which was surprising because I considered myself an expert on restaurants.

I was driving, and as we were pulling out of the apartment complex, Jenny (I guess I should mention her name) pulled out a CD from her purse and asked, “Do you mind if I play this?”

“Garth Brooks?” I said, looking at the CD.  “You keep Garth Brooks in your purse?”

“It’s never a bad time for Garth Brooks,” she said, as she looked through the mini-collection of CDs in my car.  “I don’t know any of these people.”

She put the Garth Brooks CD in, and I really didn’t like the music.  When you don’t like a music genre, there’s no logical way to explain it.  I’d even grown up around country music, and it still didn’t appeal to me.

“It’s groovy,” I said.

“Is this guy groovy?” she said, holding a David Bowie CD from twenty years earlier (the music and the album cover were from twenty years earlier, not the CD itself) .

“He was going through a phase.”

“Oooookay.  You pick the music after dinner then,” she said.

“Groovy Garth is fine with me,” I said.  When I was dating, the lady always picked the music.  That was one of my rules. “This Mexican restaurant, you’ve been there before?”

“I think you’ll like it,” she said.

“How do you know this place?” I asked.

“My ex-boyfriend.”  She said it so casually that I wanted to slam the brakes and stop traffic.

“Your ex-what?”

This wasn’t good.  She was taking me to a place that her ex-boyfriend used to take her to.  It wasn’t going to matter if I liked the place.  It could serve the best food in the world, but in the restaurant’s mind, I would always be sloppy seconds.

“Boyfriend,” she laughed.  “Ex.  We’re not dating anymore.”

“I don’t know,” I said.  I didn’t want to sound snide. “I don’t want to intrude on your special place.”

“It’s not ‘our’ place,” she said cheerfully.  “He works there.  He’s the manager.”

THAT MAKES IT EVEN WORSE, I wanted to yell, but I could only stammer, “Is he gonna… uh… be there?”

“He’d better be,” she said.  “I’m counting on it.”

At that moment, I didn’t care what kind of cleavage she had.  I was too ticked off to concentrate on cleavage.  I was ticked off that this first date that hadn’t felt awkward at all was now going to be really strange because of an ex-boyfriend.  I didn’t know that in the next few hours, though, an ex-boyfriend was going to be the least of my worries.

*****

To be continued  in Awkward Moments in Dating: Meeting the Ex-Boyfriend!

And while you wait, you can read earlier episodes of Awkward Moments in Dating!