Years ago, a former coworker who was pretty by-the-book about relationships confessed to me that she and her (now-husband) took an impromptu trip to a tropical island just a few weeks into dating. I couldn’t believe she would take that kind of chance, and yet, she was so excited retelling the story. I remember thinking, Huh. The most interesting thing I’ve done lately is see my boyfriend’s grandmother perform in a local opera. Hearing her talk about how fun this trip was left an imprint on my mind and made me realize I should probably be shaking things up from the usual dinner-and-a-movie script.
A few years later, I was G-chatting with a guy I had only been on four dates with but really liked. Important note: This was someone who I could really see myself with—the dates included hours of deep conversations, we seemed to have lots of common interests, and he had been thoroughly vetted by my wingman, Google. There was a holiday weekend coming up, and a little harmless flirting about the extra days off quickly progressed into plane tickets. Reality sunk in—was I really about to jet off with someone I barely knew? But I felt excited, not scared. Everything in my gut said DO IT, and so I did.
Did we live happily ever after? No—things fizzled out eventually. But we had a great time on the trip, and going away together fast-tracked the process of getting to know each other in a way that was certainly more exciting than doing so in our own city. Call it the Bachelorette effect: spending a whirlwind weekend away with someone cuts through a lot of the formalities of dating. You end up dealing with everything from flight delays and traffic jams to getting ready in front of each other—and since there’s no privacy when it comes to putting on foundation or curling your eyelashes in a hotel room, in a funny way, it builds intimacy. Sharing a living space is also a preview of what’s to come, and that kind of 24/7 togetherness makes it clear quickly if you’re compatible or not.
Of course, I’d be remiss not to mention the obvious downside to the spontaneous trip: What if you get there and realize you don’t like each other? It hasn’t happened to me, but is certainly a possibility. Worst case, if you land in Anguilla and he emerges from the hotel bathroom in a Señor Frogs T-shirt screaming, “Which way to the foam partayyyyy?!” you can always book an early flight home. But here are four practical tips to ensure that doesn’t happen.
If you’re going to take a trip with a new guy:
Do a gut check with yourself. Are you super comfortable with this person? Do you know that what he’s told you about himself is true? Do his Facebook and Instagram feeds add up to what he’s told you about himself so far? If there’s even one red flag or inkling that it’s too soon to go away together, put the brakes on any planning until you feel 100 percent certain.
Good to go? Stick to a long weekend—nothing more than three nights.
Make sure your expectations match up. If your idea of a weekend in Miami is lounging by the pool by day and salsa dancing by night, but his idea is more of the windsurfing and tacos variety, the trip is not going to be a success. Pick a destination that appeals to both of you.
Be up front about any sex stuff. If you’ve already gone there, cool—what’s better than vacation sex? But if you haven’t slept together yet, and you’re not sure that’s on your trip itinerary, better to let him know beforehand so you’re both on the same page.
Have an exit plan, just for peace of mind. Is there another hotel nearby where you could book a room on your own? What it cost to move your return flight up a day? Do you know anyone who lives nearby you could crash with? You’ll feel more relaxed knowing your options.
Plan a mini adventure. Chilling poolside is great and all, but adding a sunset sail or afternoon of zip-lining will ensure you don’t run out of things to talk about—and make for the perfect photo op!
If any of you have also gone away with a new guy, whether for a weekend in the burbs or a trip that required a plane ticket, let us know how it went!