Why She Slept With You: The Cocktail Waitress

Working the night shift has its pros and its cons.

Claire* looks like she was made for men. She’s got height and lips and a certain air about her. A Queens native, she recently moved from New York to Florida, where she works as a cocktail waitress at a very popular hotel in Miami Beach. She and I met while at work, serving drinks to business men, both of us playing the sexy cocktail waitress game. In between running drinks and popping bottles, we got to talking and Claire said some real shit. I was surprised to find that she was less flashy personally that she appeared professionally. But she was always honest. 

She recently became single again and she spoke to me about what it’s like to be up late and together and what it’s like to be up late and alone. 

What is your relationship status?

Single and not seeking.

Are you that fed up with men?

A little. My last relationship was actually a good relationship even though it ended really fast. It was a relationship that I wanted to have as a little girl. It was a typical fairy-tale relationship where you courted and dated before you even had your first kiss. He started off as my best friend and he was a co-worker that I pushed off for a few months, but there was something about him that made me want to continue our conversations outside of work.

How was the first time you slept with him?

He came over one night to watch a movie and he thought he was going to score and I was like, nope, not gonna happen, so we watched a few movies and nothing happened. We barely even kissed. The next morning, obviously we did and it was horrible. It was really bad.

I always say, sex is the most important part of a relationship.

I was very confused the next day at work and I told a couple of my co-workers, which I shouldn’t have because they gossip. They were like, ‘You really like him. He was really nervous, maybe you should give him another chance.’ We put a lot of pressure on our sex life. Talking about how much we enjoy it. I just think we put a lot of pressure.

Complete this sentence: Sex with him was….

Adventurous. We’re very open. We would have shifts together at work and we would open together and we would find the time to fuck at work. In the bathroom, in the locker room.


In the girls bathroom at work. There would be one employee at the bar and he wouldn’t know what was going on even though he saw us walk out of the bathroom. A manager almost caught us in the locker room.

Are you into one-night stands at all?

I’ve done it before him and after him. It helped me. It sounds weird, but this is what I do when I try to get over someone.

I guess men aren’t the only ones who try and fuck their previous relationships out of their system.

It’s not a long term thing, but I would go out with my friends and if there is someone that I’m interested in I would definitely take them up on their offer. It’s funny: For me, I don’t even have to offer it.

How do you show someone you’re interested?

This sounds horrible but I try not to talk to them at all. I don’t want to show I’m interested at all. I know that sounds really bad.

It’s because I don’t want to start liking you. If I like you, I won’t leave with you. There was this guy that I had definitely wanted to go home with; I spoke to him for most of the night and we talked about different things and I just went home because I liked him too much.

You see hooking up with someone and being in a relationship with someone on two completely different ends of the spectrum. 

I’m more spiritual now and I’m waiting for the right person but sex is sex. Now that I haven’t been in a relationship for so long, I don’t crave it, I don’t want it. A relationship, I mean.

How would you describe the dating culture in Miami in comparison to New York?

I think it’s exactly the same with only slight differences. In Miami there isn’t actually any dating. I don’t see people dating. Maybe it’s nightlife and the industry that I’m in, the fashion industry and the models. They all cheat on each other. The only thing is there is an extreme at work, the people are younger, the bussers, the runners and the drink runners, they’re either married or in relationships. So it’s a little bit of both. When you’re in a relationship in Miami, it doesn’t mean anything.

I guess you can either have a good experience with it or a bad experience with it. 

If the sex is horrible, that’s a deal breaker. I can’t do it. Even though I gave my ex another chance, I can’t do it. I liked him so much and because we took so much time dating, I gave him another chance. Otherwise, absolutely not.

*No, that’s not a picture of Claire. That’s a picture of a very lovely woman modeling for a stock photographer.

Still curious why she slept with you? Read on:

Why She Slept With You: The Unapologetic Cheater

Why She Slept With You: The Impulsive Dater

Why She Slept With You: The Recovering Monogamist

Photos by Luis Alvarez / Getty Images