Ask The Salty Waitress: Would You Ever Sleep With A Regular?

Dear Salty Waitress,

I go to a restaurant/cafe in my neighborhood regularly, and I'm pretty sure a waiter there might be interested in me. I just get the vibe! Is he just glad to see a familiar face—or is there a chance I can hit that?

Would you ever sleep with a regular?

Swooning Hard

The short answer, Swooning, is yes. Been there, done that.

Some back story: I was a lot younger than I am now, and the regular was a lot older. I was tending bar at the time, and he showered me with compliments and hearty tips. He complimented my musical taste and ability to make a decent Manhattan. Who am I kidding—it was a fucking flawless Manhattan.

I was dating someone else at the time, and while I basked in the attention of this regular, he remained respectful and I never thought it would go further than a wink and a free shot here and there.

Then I got dumped.

I'll reiterate that I was young, and took the breakup pretty hard. I stacked the restaurant's CD player (#throwback) with sad tunes and may have shed a tear in a drink or two.

On one particularly low day, Mr. Regular showed up and saw right away that something was amiss. So, when I got cut early, he asked if he could buy me a cocktail and tell to me all the ways I'd be better off without the fool that gave me the boot.

One drink led to many, and after moving to a third bar in the area, I thought: "Screw it! This guy is nice to me and I feel like shit about myself. I might as well have a good time."

It was a one time thing, mostly because I quickly found out from another regular that he was married (he told me he was separated—not so much) and I felt terrible about the whole thing.

When I stopped returning his calls, he stopped coming in. And while that was the right thing to do (he respected me enough to not make me feel uncomfortable at my place of employment), it was ultimately a bummer.

Sure, he was a lying dirtbag. But before I decided to take it to a sexy level, he was my bud! He would be there when I wanted to talk shit about Table 6, he'd help me throw out the too-drunk bro who kept calling me "sweet tits," he was... a customer I didn't hate.

So, Swooning, the moral of the story is this: if you really love your neighborhood restaurant, be careful before putting the moves on Mr. Handsome Waiter. And maybe instead of getting drunk with him after a shift, plan a friend hang with a group and feel out the vibe outside his place of employment.

Shitting where you eat is never a good idea, so make damn sure this guy is worth it before you find yourself sneaking in for your favorite soup on his off days to avoid him. Oh, and don't be a creep. Lord knows the world has enough of those these days.

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