The Dos & Don’ts Of Traveling Together (Without Ruining Everything)

11.08.18 4 days ago

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Your first vacation in a new relationship is a big deal. It means that this person likes you enough that they’re willing to throw down some serious cash (and use up their precious, limited vacation time) in order to spend time with you. And this is almost certainly because they’re (at least moderately) into you and your charming personality and general hotness and almost definitely not because this has been one long con to get you onto a cruise ship and then murder you far out to sea so they can steal that $807 in your bank account. Almost, definitely, probably not.

But with the excitement of getting to lounge on the beach together, comes some pressure. What if it’s terrible? What if you find out that they cut their toenails on airplanes or it comes up in casual conversation that they think John Mulaney is “just okay.” Or maybe they voted for the opposite political candidate as you or didn’t vote at all because “what’s the point.” Maybe every time they order a drink on vacation they sing the entire, “Do you like Pina Coladas and getting caught in the rain?” song.

Worse still, what if you’re the one doing terrible, unforgivable things to them? What if you’re the toenail clipping person?

Have no fear though, friends, passionate admirers, and bitter ex-lovers — we’re here to tell you the dos and don’ts of your first couple’s trip. Because with the right set up, planning, and basic human decency your trip can be as smooth as possible. Maybe even fun? Follow these simple guidelines and you will be well on your way to standing in an infinity pool with your girlfriend or boyfriend staring at the rainforest for as long as both shall live. Or at least until you get bored.

DO keep both of your budgets in mind when planning.

The Situation:

You’re very, very wealthy. Instead of pebbles in your driveway, you use diamonds. Instead of cat litter, you use diamonds. Instead of toothpaste you just grind diamonds onto your teeth, every night, until they’ve been grated away to dust, painfully, one. by. one. But no big deal because you can replace them with DIAMONDS.

Naturally, you’ll just pick a hotel at random from a list a friend gave you. You’re not going to give that friend’s name but it rhymes with Bark Buckerberg (coincidentally that’s also the name of a dog you have an ongoing feud with. He knows what he did).

Why you should be looking up sales or try a hotel app:

Unless you’re paying for everything as a gift, your first trip’s opulence level should be based on the financial situation of the partner who has less money. Because — spoiler alert: You’ll both have more fun if one of you isn’t worrying that this trip is going to keep them from paying rent on time or drain the money they were saving for their cat’s diabetes medication.

“No, no, it’s fine. I love 90 dollar steaks and besides, Fluffy has lived a very long and fulfilling life, I guess (strangled sob). Yep. Let’s get in the hot tub. That sounds like a good place to cry. I mean kiss.”

Look, at the beginning of any relationship, you’re trying really hard to go with the flow and be easy-going. It means that it’s much harder for your bf/gf to say no to that nice hotel you swear has the softest pillows in the world or say, “are you f-ing kidding me. You know my cat has diabetes.” when you suggest a $300 pre-fixe menu. So do your partner a favor and pick a spot that will make everyone feel comfortable and not stressed.

(Although, if you’re both rich af, do whatever you want! And also, I don’t know, adopt me? Adopting adult women is a thing you can do right? Be my new parents, please? I’m nice!)

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