How to Turn Your Vacation Fling Into a Real Relationship

Courtesy of Velas Resorts

Dating someone you meet on vacation is like New Coke, right? An idea absolutely destined to fail that, if you're really unlucky, spawns something horrifically toxic in the process. But anytime you try to articulate why it's such a bad idea, somebody in the group inevitably pipes up and says, "My cousin Jill loved New Coke! Also, she met her husband on vacation in 2001 and they just had their second baby!"
Is Jill the exception to the rule? A certifiably insane romantic? And how on earth did she make it work? We have no idea -- we don't know Jill -- but we did talk to a bunch of women like her (and tried to talk to a bunch of dudes, but they wouldn't open up, so make of that what you will) about how they turned a vacation fling into a real, lasting relationship. These are tips they shared.

NOTE: All names have been changed. And ages, maybe slightly.


Talk. Every day. Incessantly.

Texting (or, if you’re dating someone overseas, WhatsApp-ing) is great, but can also be done while at the gym, eating dinner, or, God forbid, on a date with another person. TALKING, as in actually picking up the phone/webcam, takes time out of your day. And you'll know soon enough whether this person is a high-enough priority for you to spend that time.

"We talked multiple hours a day, every day," says Julie, 31, who met her husband during the first day of a Hawaiian vacation. "We’d spend all the time we were supposed to be sleeping or studying on the phone with each other."

"We joke that we were going to invite the inventor of Skype to our wedding," said Ashley, 25, who met her now-live-in boyfriend on vacation in Miami. "We Skyped every day, and even left it on after we went to bed so we could watch each other sleep. It's cute, but ridiculous." [Editor's Note: This is actually kind of creepy. But, hey, to each their own.]

Trust. Unconditionally.

If you're the type who can't eat if your significant other hasn't texted you back in 15 minutes, this relationship is not for you. Same if you get infuriatingly jealous every time a guy posts, "Nice!" on bae’s Instagram.
"You have to truly trust that the other person is honest, loyal, and only wants you. There's no place for jealousy,” says Lindsey, 29, who met her fiancé during The Yacht Week in Croatia.
"There was always a worry about infidelity,” says Ashley. “But I trust him because he’s just very much a family guy, and his parents have been together their whole lives. I think that's helped him a lot.”


Plan far ahead when you'll see each other

People have different ideas of how long they can go without seeing someone. And despite your undying promises to "come see you soon," that word "soon" can be pretty relative. So define it and make concrete plans before you go your separate ways.
"Decide how many weeks, max, you're willing to go without seeing each other, and then make a calendar," advises Lindsey. "Ours is three to five weeks, never more, and we plan our flights months ahead. I know when I'm going to see him from now until May. We actually keep an Excel spreadsheet.”

Set a timeline for living in the same place

Once you've figured out that this person you met while getting your groove back is "The One," it's time to start figuring out who's picking their life up and moving to a new city. Because if there's no endgame, you're just wasting your time.

"The future can't seem vague forever, or it'll bring your spirits down and you'll never make it," says Lindsey. "We had goals and timelines. For example, by the end of our first year, we agreed to have a plan. Not necessarily action, but a plan. Then we could decide on a goal and work towards it together."


Spend your vacation time TOGETHER

Sorry, dude, but that golf vacation you're planning with the boys might fly if your girlfriend lives within driving distance. But now that she lives in a different time zone, guess what? Your vacation time is her vacation time, and vice versa.

"We used vacation time together," says Janie, who spent seven years with a guy she met in Italy. "If he had time off for holidays, I took time off to spend it with him. And we capitalized on vacations and used them to see each other."

REALLY learn about the other person

This doesn't just mean asking them introspective questions like, "Who's your favorite muppet?" It means learning about their family, their culture, how they treat the neighbor's dog, you get the idea. In the end, you need as much intel as possible on this person BEFORE one of you moves cities. Are they somebody you're going to immediately run from as soon as you're in the same place for more than a week? Best not to find out after moving into your new apartment in Minot, North Dakota!

"We both knew we were really type A before I moved out to Hawaii," says Julie. "So we never fought about dumb BS like the toilet seat or socks on the floor."
"I'm learning French now,” says Grace, 22, who met her boyfriend on a summer trip to Europe. "It’s such a huge part of who he is, it would be really tough to make the relationship last in the long run if I didn’t."


Take actual steps towards living in the same place

"Before he'd even graduated college, I was looking for jobs in South Florida," says Janie, whose boyfriend's family was from the area. "Then I found one and moved down there, by myself, and knew no one. I was there six months by myself and it sucked. But that's what you do, you make sacrifices." 

"Talking about the future isn't enough.You have to DO things to show each other you're really committed," says Lindsey. “My fiancé is in the process of looking for visas, and I'm looking for jobs in Europe."

When you move, have separate lives

It may be tough when one person moves to a new city to have a life outside the relationship, but it's important to establish individuality. This might include having separate residences for a while, and absolutely means allowing time for your partner to spend with his or her friends.
"When you're living long distance, it's not real. You just see each other and have sex for 48 straight hours,” says Janie. "When I moved, that's when it got real. He'd get livid when I would go out with my friends and not him. It took a while but we figured it out."
"When I first moved, I said I'm going to live by myself for a while and stay away from being really serious," says Ashley. “In the beginning, I was Monday through Thursday at my place, then Friday to Sunday we were together, like a normal relationship. But after three months we decided to move in together. It's all about knowing what both of you want and working together towards it."

Courtesy of Laura Grier

Know (or, at least, keep telling yourself) that you'll live happily ever after

"You have to stay positive," says Lindsey. "Optimism is everything, and you must have an ‘us against the world’ mentality because people will doubt you and do everything they can to discourage you."

"Now that we live together, I'm always like, 'You would think we’d want a break from each other,'" says Ashley. "A lot of people, when they do long distance, miss each other so much; but when they get together, they think it was better when they were apart. I've never felt this way. I love living with him.”

"It wasn't like I had vacation goggles on and was back to reality once I moved. Everything that intrigued me about him was still true, so that kept the spark going," says Julie. "It never seemed like it was a better idea to break it off."

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Matt Meltzer is a staff writer with Thrillist who still thinks New Coke was a better idea. Follow him on Instagram: @meltrez1.