5 Real Bartenders Share Stories Of Hooking Up With Their Customers In Secret

After a few years in the service industry, you tend to learn that servers and bartenders will rarely hookup with their customers, but could definitely be hooking up with each other (or with someone far, far removed from their restaurant). However, there’s an exception to every rule, and once in a blue moon, the people working behind the bar will end up taking a customer home, or vice versa. These five bartenders shared their customer hookup stories that they never even told their coworkers:
Drew Wilson
Drew Wilson


“When I was 28, I had a regular who was 23. He had just graduated about a year before, and he was working an internship he hated. He used to get out at 4, and he’d come into the bar for a couple drinks before the happy hour rush. After a few weeks, we had talked several times and clearly liked each other, and he started coming in only during my shifts — for the first two hours of the shifts, because I started at 3:30. I’d never been with anyone younger than me, let alone a regular customer, and I knew my manager wouldn’t be pleased. But he was so cute, and you could tell he was so attracted to me, as someone who was older, had their shit together, and gave him support. I used to take a 15-minute break right when he left the bar so we could hookup in pretty much any place we could find. It lasted about three months; he’d wait up for me when I got off, and a few times we even hooked up in bathroom of the restaurant next door, because I was friends with a few of the servers there.” — Amy, 30


“I’m 32, and I bartend in a college town. It’s like working in the lion’s den. You have all these women basically throwing themselves at you whenever you want. I’ve had a number of gorgeous girls — usually like 19, 20, 21 — give me their number, ask to meet me after the bar closes, even offer to hang out and help me close the bar. Sometimes I’m not interested at all because most of them just seem way too young, but every once and a while, I’ll be overwhelmingly tempted. Regardless, I always held back. I date women my own age, and I don’t want to give a lot of these girls the wrong impression. I gave in once, though. The girl was 20, and she was an absolute knock-out. She’d come in on Thursday nights just to talk, and a few times she invited me home afterward. She radiated confidence, which is such a rare quality, and it drove me crazy. After two months of not being able to get her out of my head, I took her up on her invitation and went home with her. It was a week before she graduated and left town. We only let it happen for that one night. And then she was gone the next week. I’ve never seen her again, but it was still amazing.” — Tony, 32


“I used to work at a bar with my boyfriend. We both worked three shifts a week, in addition to working our full-time jobs, because we were saving up for a month-long trip to Southeast Asia. It was something we both thought would be kind of fun. We were new to our city, and wanted to expand our social circle, and we both had bartending experience from when we were in college. We had a woman in her mid-30s come in a couple of times when we were working together, and it was really hard to tell which one of us she was interested in, but each time she came in, she’d stay for hours, just talking and drinking with us. She had to be about five years older than us, and she carried herself so well. I have no idea if she was married, what she did for a living, whether she had kids, or anything like that. (She only came in at nights though, so I assume she worked during the day.) My boyfriend and I had openly discussed having a threesome before, but I never figured either of us would actually pull the trigger and go for it. But it was so clear that we had the opportunity. So we took it. I invited her out with us one night, and we spent our night — from like 9 PM to 5 in the morning — out drinking, dancing, and just getting closer. She came back with us, and the most surprising part was she knew exactly what she was doing. It wasn’t her first time, and she took control. My boyfriend and I saw her a couple times after the fact, but we all knew the moment had passed, so it really only happened that one time. It was so worth doing and I had a shockingly good time, but I wouldn’t do it again. (Maybe he would, but I haven’t asked, and I don’t plan to.)” — Callie, 28


“This is a pretty bad confession, but more than once, I’ve been talking to a girl on a dating app, and then had them come into the bar during the later end of my shift. It’s the perfect semi-screened Tinder date. We talk for a little while on Tinder, and then I tell her what bar I work at, and that she should come by for a drink on me. If I don’t like her, we can just hang out for a bit, and then I say I’m working really late, and maybe we can catch up another time. (No one gets hurt, and she still gets a free drink.) But a few times, I’ve hit it off with the girl, and had them wait around until I close up. I work alone, so I have free rein of the bar after we close at 2. The best sex I’ve ever had is when I let a girl come behind the bar and make us drinks.” — Shaun, 26


I met my boyfriend through my bartending job. There’s pros and cons to all the male attention you get as a bartender. You really don’t have to be Karlie Kloss to get relentlessly hit on, and after a while, it gets so old. I can’t pretend I didn’t like the attention at first, but it just gets to be too much, and I quickly learned that I was much too introverted to truly enjoy the constant interaction, the constant flirting, and the constant instinct to become a therapist to whoever was across the bar. About two years ago, a guy came in with a group of his friends. I’d known him in college, but only through friends of friends, and we were never close. He had always struck me as insanely bro-y, with pretty much no depth, so I’d never really made the effort to get to know him. But out of his group of friends (who had all gone to school with me), he was the only one who recognized me, and then sat down to ask how I was, and genuinely wanted to catch up. At the end of the night, he left, and I assumed he hadn’t been as interested as I had been in him. An hour later, the hostess came up and told me he’d called the restaurant and asked her to give me his number. I called a couple days later, and we went out, hooked up, and started dating a couple months later. I told the hostess I never called him, and never told anyone at work about it. There wasn’t any particular reason for that, I think I just got off on the secrecy at first.” — Mary, 35 Thought Catalog Logo Mark

More From Thought Catalog