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Ladies, Please Let Me Pay

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Paying Dates

I’m far from chauvinistic. I’ve had platonic female friends to complement a fair sample of girlfriends and romantic interests, dating back to the waning years of high school. Some of these girls made more than me, and that was perfectly OK. But the prospect of the girl paying while out on a date has always made me uncomfortable.

My first serious girlfriend was a waitress – and a damn good one at that. She made bank for a server. She’d come over on days I had night class to wake me up with Subway and a blowjob. The first couple times were awesome. By the third or fourth time, I was getting pretty uncomfortable with brunch-in-bed, so I told her I was content with just a blowie. If I mentioned a concert I wanted to see, those tickets were hitting my inbox the next day. I said a movie looked appealing? I better clear my plans the next night. It was awesome, but weird. I told her, ad nauseam, to cut the shit. If I wanted something, I’d buy it myself. She didn’t listen. To her, spending money on me was a way to show affection and I wasn’t about it.

That relationship ran its course a few years ago, and now I find myself spending a lot of time alongside a smokeshow bartender with a deep purse. She’s got me by a few years and she’s a helluva good time. She out-earns me 10:1. I live on a shoestring, almost-the-hell-outta-college-but-still-broke budget and it’s tough to keep up with some of the things she wants to do. Worse yet, that isn’t always a deterrence to her.

I surprised her at her bar last week. My first Jameson and ginger ale was on my TFM money and the next six were on her. I looked at my tab with incredulity. $6.

“I know you’re tight on money, so I comped a few,” she said. It was equal parts generous and emasculating.

When I woke up the next morning, she told me she planned on ordering food and asked me what to get. I brushed aside the question by telling her I wasn’t hungry and I don’t like take-out/delivery. She proceeded to order food anyway, which cost $30 bucks, and tipped the delivery driver (who took over an hour to get to her apartment) another 10. I shot her the same look of incredulity she got the preceding night.

“I was hungry and I wasn’t just going to eat in front of you.”

Acceptable reasoning. I still didn’t like it, though.

Finally, a few nights ago, I couldn’t handle the feeling of inadequacy any longer. I took her to the classiest fucking place in town: The O Garden. We racked up about $70 in soup and house wine. I announced to the Olive Garden bartender that I would handle the check. We left the restaurant and headed back to our usual hangout spot. By then, she was tipsy and I was beginning to feel the warmth of the tequila.

“I’m only having a drink,” I told her, as the front door squeaked open. We were only there to see the regulars and catch the end of the Pirates game.

We sat down and she loudly announced to the bartender, “Kramer’s first one is on me.”

God fucking dammit. I know I just dropped a cool 70 bucks on this girl, but I still have some ground to make up, even if I’m just striving for perfect equity. Whatever. I’ll just get a 7 & 7 since that’s only $3.

“Don’t let her order me any more drinks,” I told the bartender.

Fifteen minutes later, after having my ass skinned in a game of pool, I walked back to my stool and was greeted by a tall long island iced tea.

“I thought I said I was only drinking one.”

“You always order these. It’s heavy tequila, no sours or OJ. Just drink it.”

“I’m serious this time. Last drink you buy for me.”

So, I bought her a drink. Y’know, for equity’s sake (a side note: she loves Jameson and that’s pretty rad). Everyone there knew us, but I still didn’t want to seem like the little freeloading bitch who lets a pretty girl pay for everything. I grabbed the bartender when he returned from a heater break and said, “I’m fine with drinking, but if she tries to order me anything else, either tell her no, or don’t ring it in.” I sat back down next to her and she noticed the empty glass in my hand.

“He’ll have another one.”

I shot the bartender a glare that said “don’t do it, motherfucker.” I was clinging to my man card with the atoms on the tips of my fingernails.

By that point, she was drunk and ready to throw bands. She had controlled the jukebox since we arrived and was playing an inane touchscreen game on the corner of the bar. She dropped a Jackson on the bar and the bartender slid it back.

“The house got this one,” he said. I guess it was a fair resolution. I got another long island and she didn’t buy it.

I closed my tab soon thereafter and found the pool table again. In the meantime, she had wandered into the bowels of the restaurant to fetch the on-duty bartender a few replacement bottles of liquor and drank a few gulps of fireball on her way up.

45 minutes passed and she was sloshed. She couldn’t hold her head up or open her eyes. She could only grin and slur. Walking wasn’t an option. It was time to exact my equity.

After trying to help her navigate the row of stools, I gave up the exercise in futility. I flung her purse over my shoulder, scooped her off the ground, and carried her back to my car, to the acclaim of a half dozen regulars. Fifteen minutes later, I was tucking 120 lbs of dead weight into bed, looking for a couple beers from the night before. At least my manhood was spared that night, even if the salvation came by way of carrying her out of our watering hole and up two flights of steps. That’s something I still have.

I wouldn’t call myself old school. The diffusion of gender roles allows me to shrug my hyper-masculine guise on occasion and let a girl drive or choose the movie. I’m fine with making less than a girl who works hard for what she has. But I’m not fine with her buying me things.

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Kramer Smash

Unabashed Pitt alum with an affinity for brown girls and Manhattans. Send lovelies to

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