Common wisdom stipulates that it’s best to wait until a relationship is on solid ground before heading out of town on your first trip together. Rachel Russo, dating coach and author of “How To Get Over Your Ex,” suggests doing it somewhere between three months to a year in. “Couples should go on vacation once they are established as each other’s partners,” she says.
These brave couples, however, didn’t worry about what was appropriate. Instead, they embarked on a travel dates super early in their relationships. And while it’s true not all of the couples lasted, I was surprised to find that, at least when it came to the travel date, nobody had any regrets.
An Epic First Date
Samantha Harlow, who lives in London, had flirted with a friend for a few months. “We both knew that something more was in the cards but hadn’t yet taken the step of actually going on a date,” she recalls. That’s when Harlow arrived home from a terrible day at work to “an email in my inbox with a boarding pass to the south of France for the next morning. There was a message explaining that he thought I deserved a weekend getaway and hoped that I would join him.”
The bold move took her by surprise. She told her friend and admirer she would need a few hours to consider his offer. She decided to go for it. Harlow says, “We actually ended up on different flights, so he didn’t know that I was going to show until he called me nervously whilst I was going through airport security. He did sound extremely relieved!” The two had an epic first date in the French sunshine. “New adventures helped us avoid any of the usual first date awkwardness,” Harlow says.
Her date was right — a trip cheered Harlow up after a stressful few weeks at work. Her nerves subsided enough for her to thoroughly enjoy a weekend of drinking wine, feasting on local food, relaxing on the beach, and getting to know her date. Although the relationship didn’t ultimately work out, Harlow is glad it happened.
…Or Fifth Date
On Lauren Kester’s fourth date with her ex, she bought plane tickets for their fifth date. They had both just watched the “Master of None” episode where Aziz Ansari takes Noel Wells on a date to Nashville (this was well before the semi-recent Ansari sexual misconduct allegations came out). Over drinks at a bar in Brooklyn, the two decided to follow suit and head to a city where neither had been. They chose New Orleans, and they left the next day.
Kester remembers the trip fondly: “There are a million clichés I could have used to describe the weekend. We held hands and walked in the French Quarter, met up for late night sazaracs with a friend of mine, and ate the best grits in the world at Cochon.”
Kester admits that spending three days with someone she didn’t know all that well in an Airbnb in a new city was a huge risk. But the two got to know each other better and found that their curious-yet-laid-back travel styles meshed, which was important to Kester in a partner.
Although the couple is no longer together, Kester found one enduring love: New Orleans. “Nine months later, I jumped at the chance to work on a movie here,” she says. “I’ve been a New Orleanian ever since.”
Happily Ever After
A month into their relationship, Carol and Derek Todd had a good feeling about each other, and they agreed they wanted to do something a little bit daring. Since both love to travel, they flew to Mexico for vacation. “You learn a lot about someone when the airline loses your luggage and you only have what you’re wearing for the first two days,” Derek says. “We got caught in a rainstorm the night we landed and ended up having a wonderful impromptu dinner in the closest restaurant we could find — drenched. It could have gone horribly, but it turned out to be amazing. That’s when you know you’ve got someone special.”
“It was the best trip of my life,” says Carol. “And it was where we said ‘I love you’ for the first time.” The Todds have now been married for 22 years.
So Should You Do It?
Taking a trip with someone is big step. You’re pretty much stuck with them in an unfamiliar environment. (It’s much easier to skip out on a bad meal than a bad vacation.) But if you trust your date enough to be on your own with them somewhere new, go for it.
“A whole human life is more or less one long-term road trip — it’s a series of explorations through different places, phases, and moments,” says April Darcy, who went on to marry her college road-trip buddy. “Better to learn early on if you’re going to be good companions or terrible ones. I ripped that question off like a band-aid and never looked back.”