In For Summer: Going On Vacation With Your Situationship

“So, Ben* and I are going to Hawaii together,” my long-distance bestie Grace* announced on one of our spontaneous catch-up calls back in April. “Which one’s Ben?” I asked her. All I knew was that my girl had a roster — not a boyfriend.

The 25-year-olds had met about two months prior on Hinge, and it was a classic situationship: no label, no exclusivity, and no clarity on who they were to each other. So, naturally, they were taking on a six-hour flight to a five-day vacation in Hawaii. As her platonic soulmate, I had concerns. Did they know each other well enough to be travel buddies? Would she get more attached and consequently get her feelings hurt? Did they both have TSA PreCheck?

Despite these risks, plenty of Gen Z women are going away with their situationships. On TikTok, they’re cataloguing their experiences, sharing vacay videos alongside the text, “this and my fav situationship” and “situationshipped so hard we went to Puerto Rico together.” It may feel like a chaotic move, but for some, it’s worth the airline miles. And it turns out, you can come back from these baecations unscathed... well, mostly.

Travel Is The True Compatibility Test

A week after our phone chat, Grace was sending me mirror selfies from their Hawaii hotel room, and my mindset went from concerned to jealous. They relaxed on the beach, went snorkeling, and embarked on scenic hikes around the island. Like every vacation, things went wrong — planned activities got rained out, and he had more than a few work calls to take. But those speed bumps ended up revealing Ben’s greenest flag of all.

It was like, ‘Oh, sh*t. This was just supposed to be a silly sleeping together thing. What do we do now?’

“He never complained once and was so happy to be there,” she told me afterward. “Not everything was going perfectly, but our general attitudes were aligned.” In theory, vacations are relaxing, but jet lag, flight delays, and lack of alone time do not always bring out the best in people. So the fact that Ben and Grace continued to like each other revealed pretty quickly that they were a strong duo. “It's such a fun way to get to experience a new person, a new place, and kind of fast-track a relationship. You're getting to see who they are right away,” Grace says.

Grace and Ben became official not long after their romantic getaway. “How can you be on a trip for five days with someone, talk to no one else, and not have feelings for them?” she says. Since the vacay, Grace has cleared the roster, and Ben isn’t just her travel buddy: He’s also her boyfriend.

It May Spark Feelings Without A Deeper Commitment

When Lily found herself locking lips with her situationship under the Northern Lights, the dynamics were anything but clear. The 23-year-old was living abroad in Copenhagen, and her love interest (“unfortunately American”) resided just down the hall. “It started as an accidental drunken hookup, and it kept continuing as a matter of convenience. We were on top of each other all the time. Literally, figuratively, all of the above,” she says. He mentioned offhandedly that he and his friends were taking a weekend trip to Norway. “I was like, ‘No, I'm coming too,’” Lily says. “I, too, would like to see the Northern Lights.”

Their vibes began as purely physical, but everything changed once they started playing house on the trip: cooking in the Airbnb, going grocery shopping, and why was it hot watching him take off his belt for TSA? It all felt very domestic. Add in the Northern Lights and a dog-sledding date, and it was a surefire recipe for getting attached.

“Neither of us wanted that emotional connection, and then we were faced with it,” Lily says. “It was like, ‘Oh, sh*t. This was just supposed to be a silly sleeping together thing. What do we do now?’” They swept their feelings under the rug, and once they got back to Copenhagen, their close quarters turned from a blessing to a curse: Lily’s American boy brought home another girl. Right when she got invested, he screwed it up. They officially broke things off, but that didn’t stop Lily from backsliding a few times — that’s what situationships are for, right?

You May Find It’s The Ideal Arrangement

And yet it is possible to catch flights, not feelings, and still have a great time. Faith, a 28-year-old living in Nashville, did the impossible and went on vacation with her situationship (her ex-boyfriend, no less) without ruining the vibe. The pair had been on and off for years, but even when they’re off, sex stays on the table. “We had come to terms with the fact that it was not gonna work out,” Faith says. “But that didn't stop us from seeing each other until we found the right thing.”

I loved that he was bankrolling it. Like, what do you mean, I get a sugar daddy who's not old?

They planned a trip to Miami after she casually brought up the idea to him. “I had mentioned how badly I wanted to go on vacation but didn't want to pay for it,” Faith said. “And he said, ‘Tell me where you want to go. Send me the flights and hotel, and I'll book it.’” But Connor wasn’t without his own conditions. “The only caveat,” he told her, “is that I also want to buy you a couple of very revealing bikinis, so you’ll fit in on the beach.”

She was just as turned on as I was hearing this. “You mean I get new swimsuits and a free vacation? Totally down,” she laughs. When I asked how she felt about Connor financing the trip, her response was equally enthusiastic: “I loved that he was bankrolling it. Like, what do you mean, I get a sugar daddy who's not old?”

A few weeks later, they were off. The pair had traveled when they were officially together, but this trip felt different — not only were they less couple-y, but they bickered less, too. The focus was purely on having fun, which translated to drinking on the beach, taking edibles, trying local Cuban food, and banging it out in the hotel room.

Post-trip, they kept up their hookups for a little while, until one of them got into a relationship.

Brace Yourself For A Turning Point, For Better Or Worse

While taking a situationship to the beach was the perfect arrangement for Faith, for 38-year-old Jen* it was a disaster. Ten years ago, she traveled with her situationship — an NYC-based DJ, no less. They started like Grace and Ben, seeing each other pretty consistently without a label. They journeyed to Miami like with a casual “Let’s go somewhere warm together!” And went on to discover, Jen says, “The trip was the end of everything.”

Her man’s sister happened to live in Miami, so Jen found herself meeting the family — without even knowing what she was to Mr. DJ, who loved to give her emotional whiplash (i.e., “I just can’t date right now! But wait actually I’m obsessed with you!”)

Spending time with his fam on a couple-y trip only made things more confusing. “It made me realize that I really did want to date him, and that’s not what we were doing,” Jen says. On the trip, she also found out he was seeing someone else — Mr. DJ mentioned “some girl” had recommended a TV show, and Jen’s intuition started ringing. (Spoiler alert: he’s married to “some girl” now.) Once she got home, she decided she never wanted to speak to him again.

Coming to us from the future — happily married and f*ckboy-less — Jen can offer some sage advice re: situationship vacations. “Get really clear on your expectations for how it'll affect the situationship, and prepare to have it be a turning point,” she says.

Grace and Ben DTRed, Lily and her American boy said goodbye, and Faith defied all odds with upfront communication and outlined expectations. How did she not catch feels? “We were very upfront that ‘I’m using you for a free vacation, and you’re using me for sex,’” Faith says. “The dynamics were clear, and I think that made it a lot easier.”

If you’re able to keep that in mind, there’s no reason you can’t have a sexy situationship getaway this summer. Bon voyage and have a safe flight — may your tans be golden and your status at least somewhat defined.

*Name has been changed.