Making a Move at the Uptown Diner

5887770030_8a3da50f2d_bHe walked into the neighborhood diner on Saturday morning not exactly dressed to impress.

On his way to play some hoops, he sported athletic shorts, a baseball cap, last night’s button-up, and flip-flops. But what did it really matter? The idea was to quickly fuel up on Eggs Benedict — a dish he’d enjoyed at this particular diner with just the company of a book or newspaper many times before — then hit the road and head to the park for some pickup ball.

As is typically the case during weekends, the place was packed, and there was just one spot open along the bar. He walked through the dozens of people waiting to be seated by the entrance and perched himself atop the only available stool. Surveying his surroundings, he noticed, to his surprise, that there appeared to be a very attractive blonde woman sitting directly to his left. Not only that, but she looked to be by herself.

Her initial appearance gave the impression that her morning might be unfolding in a manner similar to his. Her eyelids were covered with a good bit of makeup — probably applied today, he guessed, though it could’ve been a remnant of last night — and she wore loud pink biking shorts. The shorts combined with the makeup made him wonder whether she was headed to a daytime festival of some sort, or, like him, expecting minimal human interaction while chowing a quick breakfast.

As he settled in, she looked up from her menu long enough for their eyes to meet, and he realized she was just as good looking as his initial impression suggested. There was also no ring on her left ring finger, which was something he’d gotten in the habit of looking for in situations like this since sometime not too long after college.

Now came the hard part. A product of the internet age, he was used to his flirtations taking place via some sort of digital medium. As an introvert who made his living writing, that sort of thing played to his strengths. Making a move in person, especially in a case where it was unclear whether the target of his flirtation was single or even the least bit interested — he was wearing shorts and flip-flops, after all — wasn’t something he was used to or particularly good at.

But as her gaze returned to the menu, something in the air seemed to suggest she expected him to chat her up, though he couldn’t discern if that prospect at all appealed to her. He realized he had nothing to lose but much to gain. Nonetheless, an awkward silence ensued.

Finally, he worked up the courage to say something, anything.

“Come here often?” he asked, immediately regretting the lame icebreaker.

“Yeah,” she turned to him and replied. “You?”

A faint smile revealed her perfect pearly whites while he scrambled for something remotely interesting to say.

“Yup,” he offered. “If you’re in the neighborhood, it’s a good place to stumble to for brunch on the weekends.”

The server came by and they both ordered. She opted for some sort of “meat lovers” dish, while he went with the Eggs Benny.

“Is that your regular order?” she asked, buoying his optimism with the unprompted question.

“Yeah,” he replied. “It’s solid.”

They went on to talk briefly about their respective places of residence — she told him she used to live in the neighborhood but had since moved to the suburbs — and whether she was planning to go to a block party happening just down the street later that day (she wasn’t).

At a certain point the conversation tapered off. He worried that asking her another question would make him a pest. She buried her face in her phone, and he followed her lead, in part because sitting there glancing around the room or staring into space would just heighten the awkwardness.

After some time, he was left to conclude that, for whatever reason, his interest just wasn’t reciprocated.

The food arrived and they ate in silence, each preoccupied with their devices. She chowed, paid her tab, and while getting up to depart, said, “Have a good day.”

“You too,” he replied.

As she walked away, he asked for his bill and reflected on the interaction. Not his finest performance, he thought, but in fairness, it was unclear from the get-go whether there was any chain of words that could’ve altered the outcome. For all he knew she was heading home to her live-in boyfriend. That sort of ambiguity is a big difference between in-person interactions and ones mediated by online dating apps, where at least you know the person you’re chatting with is on the market.

He paid his tab and left, hoping the fates would arrange things so he’d be better dressed the next time an opportunity for fortuitous flirtation presented itself — or that he’d be lucky enough to plop himself down next to someone who was interested despite the basketball shorts and flip-flops.

Image credit — Michael Rosenstein on Flickr

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