Awkward Moments in Dating: The Cheapskate

(image via wikimedia)

It’s good to be a cheapskate sometimes, but not during a first date.  When I was in my mid-20s, I had a decent job, but I had blown all my savings and had maxxed out a couple credit cards on a really attractive girlfriend. Even though I knew at the time I was making a bad decision, I didn’t care.  But I cared after the really attractive girlfriend broke up with me.

When I told my platonic friend Suzanne (You can get more details here) that new prospect Kimberly wanted to go to a place called Ted and Johnny’s on our first date, she actually sounded excited.

“That’ll be fun!” she exclaimed.

“It’ll cost a fortune,” I said.  Ted and Johnny’s was a giant arcade place for adults with several restaurants and a bowling alley and a dance hall and a sports bar and everything was overpriced.  I could go with my friends and limit my spending to the video games, but once a woman got involved, things would always get expensive.

Suzanne didn’t understand that I was living paycheck to paycheck, trying to get my credit debt wiped out as quickly as I could.  Maybe I shouldn’t have been dating at all.  But if I waited too long, I’d start going bald.  Physically, I didn’t have all that much in my favor, except I was tall and had decent hair and could look okay in the right clothes.  Once I started going bald (I knew it was going to happen), finding the right woman would become even more difficult.  Suzanne knew about the balding in my family.  She didn’t know I was broke.

“Do I really need to let her win at everything?” I asked.  That was another potential problem with Ted and Johnny’s, the competitive focus of so many activities there.  If a man got too competitive, he could tick off his date or girlfriend.  If he let his date win, he could come across as a loser.

”50-50 is fine,” Suzanne said.  “But pay for everything.”

Of course, I was going to pay for everything.  I didn’t have much money (I pulled some cash from the ATM, which we actually had back in the 1990s), but a man always pays.

Kimberly wanted to meet me at Ted and Johnny’s, which struck me as weird because of her history of being stood up by guys.  We planned to meet at 7:00 in the Ted and Johnny’s lobby, and I arrived ten minutes early just in case.  I could have arrived just in time to make it look like I didn’t care, but I cared a little bit, and didn’t want to come across as a guy who would stand her up later.

When I walked in, she was already standing in the lobby, staring straight at me.  I was almost annoyed.  I had wanted some time to get a feel for the place, put myself in a strategic location, find all possible exits in case of emergencies, and get myself composed.  Plus, I wasn’t sure what our proper greeting should be.  A hug would be inappropriate, but standing there with a gap between us would target us as a first date to all the people watchers.  Despite being a people watcher (in an entirely appropriate way), I dislike being the target of people watchers.

“Where I work, 15 minutes early is on time,” Kimberly said.  “You’re late.”  She hit me on the shoulder.  I liked her for that.  It reminded me of horsing around in high school.

“Oh yeah?” I said with a fake tough guy voice.  “Hit me again.”

This time it was a solid punch in the exact spot as the previous punch.

I was glad she was already comfortable enough to affectionately hit me in public.  Then again, my previous girlfriend had pulled a knife on me right before we broke up.  Maybe violent women were attracted to me.  I told myself to worry about that later.

The date was fun, except for the money part.  Dinner by itself was almost $100 (and this was in 1993).  I made sure that Kimberly saw me tip at the restaurant.  Maybe I shouldn’t have worried about the tip, but it wasn’t the waiting staff’s fault that I was broke (or that I was a cheapskate).  I actually bowled pretty well, which was unusual, and she handled the losses graciously.  She watched my back in the shooting games, and ran me off the road in the racing games.  Most importantly, she was pretty good at pool.

“Do you have older brothers?” I asked suspiciously.  Most women I’d met who were good at pool had older brothers.

Kimberly smiled and nodded.

“Did they beat up guys for you?” I asked.

“A couple times,” she said.  “So watch your step.”

Ted and Johnny’s was a great place for a first date because we could walk around and interact and watch others.  We saw a nervous guy spill his drink in front of his date at the restaurant.  We saw a guy and his girlfriend get into an argument in the lobby as we passed by.  While we were bowling, we saw a boy (maybe eight years old) get yelled at by his mom, and then the dad laughed, and then the mom yelled at the dad for laughing, and then the dad yelled at the mom for yelling at him in public.

“Wow,” Kimberly said.  “A situation where everybody is unlikeable.”

“I blame the kid,” I said.  “I’m sure the parents were perfectly happy until he came along.”

Kimberly hit me on the shoulder again, same spot. “He might hear you,” she said.

“The guilt would probably do him some good.”  Just so you know, I was kidding.  Guilt is bad.  Kimberly knew I was kidding.

Despite my mood, I cringed a little every time I had to throw down another twenty dollars.  Even though I was having a good time, the money was adding up, and I had pulled out too much cash for this date.  I wasn’t going to mention it though.  If things worked out, dates could become less expensive.  I just had to get through the first couple of them.

After a few hours, Kimberly suggested we go to a late movie and maybe hang out after that.  I hadn’t expected a movie, but I couldn’t say no.  A movie wasn’t that expensive, unless she went crazy at the concession.  She said she had a newspaper in her car, and we could look up the showings and drive from there.  If an attractive woman wanted to extend a date, I’d let her, so I followed as she led me to her car.  For some reason, she had parked in a far corner of the lot, and it was kind of dark (not dangerously dark), but Kimberly just stopped as we approached the end of the parking lot.

“Did you forget where you parked?” I asked.

She didn’t say anything at first.  She took a couple steps forward, stopped, and then took a couple more steps.

“That’s mine,” she said.

I know nothing of makes and models of cars I don’t drive, so all I remember is that she pointed to an obnoxiously huge black pick-up truck.  I could see why she didn’t want to park it closer to the Ted and Johnny’s; the truck took up more than one parking space.

“Cool,” I said, even though I knew nothing about it.

“No,” she said.  “Not cool.”  Then she pointed to the back of the truck.

I walked closer and saw what she was pointing at.  The rear window of her truck was shattered, and a bunch of stuff was strewn all over the back.  It was an expensive truck.  It looked like expensive stereo equipment had been pulled out by thieves.  Even in the darkened parking lot, it looked like Kimberly was barely keeping her composure, and I felt that all too familiar sinking feeling in my gut.

Dang it, I thought, I really hoped Kimberly wasn’t expecting me to pay for all this stuff!

To be continued next week!

And in the meantime, start at the beginning with Awkward Moments in Dating: Just Friends .