Falling In Love With Waitresses


I was at Cheesecake Factory the other night with my good friend Simmer and our waitress was more or less one of the most beautiful women I’d ever seen. Simmer and I were in animate conversation about our mutual woes in the fem category, and when she came over, introduced herself as Britney and smiled and asked for our drinks, system crash. I think I said Arnold Palmer, but I’m not sure.

“I’m on tilt,” I told Simmer, once she walked away.

“The biggest tilt,”  he responded, ‘tilt’ being a term he and I instituted to conveniently cover feelings of angst, or despair.

“Why can’t we ever have girlfriends like that waitress, Simmer?”

“You’re tilting.”

“I know I am. I agreed with you in advance. But it’s a legitimate question. Is it not?”

“Dude, velesh,” he said, which means—let it go, drop it.

She brought us some warm bread and butter. When she asked me if I wanted any appetizers to start—avocado egg rolls, tex mex?—an amazing smile, sort of like a smiley emoticon, I said sure, yeah, yeah— resemblant of the emoticon with the hearts as eyes.

Mordam,” I told Simmer, meaning, I’m a dead man.

I referred back instantly to Catalina, who once served me a perfect medium rare steak at this Argentinian restaurant in West Hollywood. Her English was not very good but I told her about my appreciation for chimichurri, and she got happy. I tried to drop more knowledge of Argentinian culture, but chimichurri was the extent, sadly. Catalina was petite, curvy and had wild curly black hair. That night I knew I was probably in love with Catalina, and for the latter half of the meal I berated myself over what I could possibly tell her before I left. At the end of the meal, I said, why don’t we get coffee some time, and she laughed and said I had nice hair and a cute smile, but she was married.

There were several more of these examples. With waitresses.

Britney came back to our table and brought us the appetizers, which I shouldn’t have ordered. I slipped in a little joke and she laughed. I turned to get some analysis on Simmer’s end, raising my eyebrows as she patted my shoulder and walked off.

“Look. It’s their job to be nice. Don’t get the wrong idea. I’ve been down that road. It’s a road of endless tilt.”

I think my good friend Simmer had it right, and this will cue in as our #1: It’s their job to be nice. It’s rarely a black and white situation inferring whether a woman likes you. But I think that if she’s talking to you, seems friendly and energetic, and not speaking to you out of obligation, you can probably assume she at least likes you as a person, and you can go from there. With waitresses, though, not only are they obligated to talk to you, but to be very courteous as well. With that, you’ll never know whether it’s because she actually finds you cool, or is just playing the part to get a bigger chunk of your wallet. An obvious point, I guess, but essential in understanding waitress science.

The second strongest sticking point, I think, is that you’re implicitly battling infinite competition. Let’s say that you and Lovely Waitress have gone on a few dates, follow each other on Twitter and all things are turning out well. In twenty years of waitress pursuit (yes, I’ve been hitting on waitresses since I was five) I’ve yet to accomplish this much, hence the cynical title (once actually—but she was a barista). But let’s assume you do go this far. How do you feel knowing that as long as she remains a waitress, she is going to meet dozens upon dozens of men who will probably find her lovely too? Further, in light of evidence that she finds customers as fair game, what’s to say she doesn’t leave you tomorrow for the next witty patron who can slip in a nice pun about his fondness for a well burger? A waitress at a popular restaurant serves hundreds of men a week, if I’m correct, and I am—this is my article— all of whom she must talk to a couple of times. Here is where you agree, say that, hey, I never thought about that.

“So have we thought about main courses?” She asked now, whipping out her black, leather pad. She wore the standard all white Cheesecake outfit, and I typically hate those things, but she bequeathed it with lovely appeal.

She took our menus and walked off, blonde hair bouncing behind. There was something to her, I observed, as Simmer told me a sad story I wasn’t listening to. The way she spoke to people was magical—totally present, energetic. She was the opposite of this girl I hate, a girl I dated, who always had interesting things to say, but made them sound very boring. Britney the Cheesecake waitress though, talking about appetizers and bread and butter, turned this stuff into fabulous subject matter, simply by her captivating tone. What I mean to say is, while awaiting the entrees, she came over to ask: “Everything okay? Do you want more butter with that bread?”

Suddenly I said: “Yeah, totally. I would actually love some more butter,” when in reality, I don’t even like butter.

Waitresses. Definitely an exciting form of romance, not quite forbidden—say, like a teacher, TA, a coworker—but an underlying adventurism surely rests in the idea. Simmer kept telling me his story. I told him to look on the bright side of things and to be grateful for what you have, not what you can have, which I knew sort of didn’t make any sense.

“How was it, guys?” she asked us.

“Great,” Simmer said. “Thank you.”

“Now, can I get you guys something for desert? Some cheesecakes?”

“We’re stuffed,” Simmer said.

“I would love a cheesecake,” I said, although if one more calorie entered my body, I thought, after bread and butter, avocado egg rolls and an entree that could feed two, I’d probably mentally collapse. “But oh. I’m mad full,” I said.

“Oh! That’s okay! How about I wrap one up for ya and you enjoy it for breakfast tomorrow?”

I didn’t think.

“That’s a great idea,” I said. I ordered one with strawberries and she walked away.

“Do people even eat cheesecakes for breakfast?” I asked Simmer. I didn’t know.

“You’re a clown. They should call you Mister Tilt.”

A few minutes later, she came over to say that it was a pleasure serving us, handing me my cheesecake, which I still had no idea why I ordered, inside of a knotted to-go bag.

“Thank you!” I shouted, wanting her to hear me, remember me, something, I don’t know. Only one time have I heard about a waitress quest gone right. It was when my friend from Philly gave me a call to catch up after a few months.

“By the way dude,” he said. “I got down with this waitress I had.”

I instantly took offense to this news: were all my theories wrong? Is romance with waitresses doable, something that I’m just overanalyzing?

“Wow. How’d that happen?” I asked.

“I left my number on the receipt, and she actually hit me up. Met me up at a bar.”

“My god.” I envisioned this with Leila, the waitress at the local sandwich shop who remembers my name. Or maybe even now with Britney, given that she had just handed us the bill.

“Well, what’d she look like? Is she cool?” I asked.

Here is where he hesitated and assuaged the conversation into law school — something about the LSAT, or the bar.

“Tell me more about the waitress,” I pressed. “Is there a future here?”

“It’s a cool story, okay? Let’s leave it at that.”

“Hey, don’t get so touchy.”

There was a silence.

“Look—If I wasn’t drunk, or if she wasn’t my waitress, I would never go near her. Not with a ten foot stick. There. I let it out. Happy?”

Yes, I was happy. My theory prevailed and I rested my case.

We paid the check—somehow a meal I planned spending twenty-five on came out to forty-five. Britney was settling in the table next to us.

It’s also probably the social aspect. Pretty waitresses know how to talk to people, say things the right way: manners, enthusiasm. I looked at her one more time and she turned around and smiled at me, just as Simmer and I stood up.

“You know what, she actually was pretty nice to you. Maybe leave your number. See what happens,” Simmer said.

I looked at her one more time. I overheard her convincing this couple to take a few cheesecakes to go. “Some for breakfast, huh?” She asked. Just like for me.

“I’m tilting. Forget it,” I said, and we walked out. Thought Catalog Logo Mark

More From Thought Catalog