9 Work Trip Stories That Show Business Travel’s Wild Side

Traveling for work often evokes the image of a lonely, sad business hotel room, but nowadays, many companies have attempted to revitalize the image of retreats with poolside parties, camping getaways, and mansion rentals. Let’s be real, though — these getaways tend to breed tea more often than “team synergy.” Stuck in a resort house with unlimited free drinks, your work besties, your watercooler archnemesis, and human resources? What could go wrong?

That’s the premise of Very Bad Company, a new novel about a business-retreat-turned-crime-scene by BDG Chief Content Officer Emma Rosenblum. Trendy tech startup Aurora gathers the company’s top employees for an exclusive retreat in Miami, and this year, Caitlin Levy — Aurora’s newest hire — is joining the team as head of events. When a fellow high-level executive disappears on the first night, Caitlin and her colleagues have to decide whether to keep up the charade of team-building exercises and lavish dinners, or derail the company’s future.

Here, 10 women share some outstanding memories from their company-sponsored travel: the salacious, the spooky, and the surprising.

Getting Down To Business

“I was staying at this really nice hotel on the company’s dime and spontaneously invited this guy I’d been seeing. At the promise of five-star-hotel-room sex, he dropped everything and booked a flight. We f*cked all week, once while he was on AirPods and had to speak during a conference call. On our way to the airport, he broke up with me. He’d previously made me switch my flight so we could sit together, so I was stuck crying next to him for three hours on the plane.” — Vanessa, 30

“I went to an island for a glamping trip for work, and since the ferry stopped running at 6, the event staff had to stay overnight with us. I ended up getting drunk and hooking up with one of the hot production guys in his tent. The next day, everyone was gossiping about whether one of the other girls on the trip had slept with the photographer. They had no idea I was actually the one who had sex.” — Jessica, 28

One woman hooked up with an event staffer on a glamping trip for work.

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“I got on Bumble to find a tour guide, ideally one with benefits. I matched with six men just by posting some hot selfies and saying I was in town for the weekend. I made them pitch themselves and chose the one with the best banter. He showed me the coolest parts of the city, we bar-hopped, and I took him back to my hotel. When we were kissing, he said he didn’t have a condom. I was like, ‘OK, then it’s gonna be a no.’ He suggested we go to his place (medium-level crusty, I’ve seen worse), we had sex, and then he asked me to stay over. I was not sacrificing a comped hotel to sleep on a man’s navy sheets, so I called an Uber and slept until 1 p.m.” — Ali, 29

“I interned at a consulting firm for two summers, and both years, I got flown out to their training facility. There was this really cute guy there, and I was like, ‘Let’s hang out.’ We kiki’d around, and at the end of the night, I was like, ‘You should come to my room.’ Mind you, everybody in this hotel works with us, and there are cameras everywhere. He was like, ‘You know I have a girlfriend, right?’ I was so stupid and so f*cking horny that I was like, ‘I don’t care. Do you care?’ We ended up having sex, but his d*ck was so big that we struggled for a long time to even put it in.” — Luna, 20

Corporate Chaos

“The company flew us all out to a gorgeous luxury house in Mexico. We were jet-lagged, but our CEO had hired a mariachi band to perform, so we had to stay. He tried to get employees to dance with him, grabbing people’s hands and spinning them around in circles, kind of like the Hokey Pokey. There were a lot of limbs flailing around. One person indulged, but the rest of us were standing along the walls trying to look enthused as he was making his way around the circle.” — Jolene, 22

“After my co-worker and I went to Stockholm for work, we went to Amsterdam together for fun. I thought we were going on a little idyllic bike ride, but he ended up dragging me into a 26-mile tandem ride. We had to throw our bike over a fence because he refused to take seriously a Dutch sign that said they were doing construction. We got stuck on a beach surrounded by tractors, and for 45 minutes, we were pushing the heavy-*ss bike on sand. At one point, there was a traffic jam caused by a bunch of cows. The thing is, we didn’t fight once the whole time. It really improved our teamwork. I think low-stakes shenanigans bring out real camaraderie.” — Melissa, 26

Meetings From Hell

“I had a consulting client who knew how to get down. On the final night of our trip, we got a little tipsy at a boozy mini-golf course. She invited us back to her place. She was like, ‘I do birth chart and tarot readings.’ I asked her if she would do mine, and she did. She said, ‘I see you dying alone. You’re not going to meet anyone ever. That’s just what’s in the cards for you.’” — Piper, 26

One work trip involved a morbid birth chart reading.

Engdao Wichitpunya / 500px/500Px Plus/Getty Images

“On my first work trip, I took a shower before meeting up with co-workers. As I was getting ready, the mirror started to fog up and I saw writing on it. It was backward, but from right to left, it said ‘MURDER, GET OUT.’ I was naked and alone, and was like, ‘Is this real? Should I hop in the shower? Is this a big joke?’ I took a photo of it and ran. The lady at the front desk didn’t even ask me any questions and just offered to give me a new room.” — Rayee, 22

“We got put in a really old hotel. The first day, I had this sense that someone was in my room with me. I felt a little sick and had really restless sleep. When I woke up, I was freezing and had a cold, fever, and runny nose. I tried to tough out the morning activities but ended up going back to my room. Then, in the middle of my nap, I felt something tugging on my bed covers. There was this feeling of pawing, like something was using both hands to claw the bedsheets. It was completely dark, the tugging was nonstop, and I felt the bed start to shake. I opened my mouth to scream and woke with a start. Later on the plane, I relayed the story to my colleague, and she told me she had felt a similar eeriness in her own room, the one exactly below mine. As soon as we landed, my sickness disappeared completely.” — H., 25

Interviews have been edited and condensed for clarity.

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