Taking Her On Vacation? 9 Things To Keep in Mind When Planning Your First Trip

Planning Your Overnight Excursion

Some people say that taking a trip with someone is the perfect way to tell if you’re really compatible or not. Or if you even like each other as much as you think you do. That’s because it serves to concentrate the experience of being with that other person, which means it’s more intense in the good ways and possibly in the challenging ways. Taking your first trip together should be super fun, exciting, and romantic, but it’s also good to be mindful going into it. Here are some things to think about when you’re getting ready to take your first trip together.

1. Choose a destination that you’re both into.

This might be the first time that you spend multiple days together without a break, so you want to make that transition a seamless one if possible. Choosing a destination that you’re both actually interested in is a good idea to avoid disharmony the first time around.

You don’t want to do something too mellow if your girl is an adrenaline junkie, but you don’t need to be backpacking through a foreign country if that seems a little extreme on the other end. If you don’t agree on what sounds like an ideal vacation, try to find a middle ground so that neither of you feel like you’re the only one compromising.

Relationships require a lot of compromise, and when one person does more than the other it can come back around when things go wrong. Think about how resentful you might be if the vacation is a total disaster and she planned the whole thing or vice versa. That’s not necessarily a fair feeling since there are a lot of factors involved in how a vacation goes, but might as well cut out that possibility for the first time that you’re giving it a go.

2. Ideally keep it short and sweet.

When you can, it’s usually a good idea to do a weekend trip before committing to anything too crazy. It’s long enough to have a good time, but not so long that you’ll be panicking if you suddenly discover that you hate each other. Sometimes this isn’t possible since the reasons for trips vary. Maybe you’ve got a work gig or you’re accompanying her home for a family matter.

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No matter what kind of trip it is that you’re planning, try to both get involved in the process but play to your strengths. The foodie comes up with some must visit cocktail bars, and the organized one schedules the rental car.

3. Prepare for the unexpected.

Since there are literally so many moving parts involved in vacation, there will often be unexpected things happening. Hopefully it’s less like the airlines losing your luggage and more like getting upgraded to the honeymoon suite on arrival, but you never know. Sometimes there’s an added stress of unknown when you’re on your first trip with someone, which is fine, but just be aware of that so that you can try and remain calm if anything gets complicated along the way.

Stress tends to breed more stress, but no matter what happens you’re still on a vacation, so it’s probably not that bad. In retrospect the craziest vacation blunders make the best stories anyway. It’s a novelty, it’s outside of our normal life, so once the emotions subside it’s actually funny to recall.  Remember that it’s an adventure through and through, and the best adventures do actually include some unexpected things.

4. Try something that’s new for both of you.

If you’re on a romantic getaway you might be tempted to spend all of your time in bedroom. There’s plenty of time for that, but there’s also time to get out and explore wherever you might be staying. Ideally you can find some activity that’s new to both of you that you discover and try and out together.

Even if you’re just on a staycation at a nearby hotel or something, make an effort to talk to other people staying there, or try out a new cuisine. Anything that you can do as a team effort that’s different than your average day will help to create that new experience feeling that a vacation should. Don’t cling to the ordinary otherwise you might head home without any memories from the trip.  

5. Take time apart if you need to.

If you run a side-by-side list of your top priorities on a trip and they’re very different, it might make sense to have an afternoon apart to make sure you both accomplish what you set out to. Of course the overall point of a vacation with a girlfriend is to spend time with your girlfriend, but if the relationship is sticking around then it also makes sense to treat the vacation like the rest of life in that sense.

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At home you don’t spend everyday together because you have different stuff to do. If you’re really set on a getting a massage by the beach but she would rather go for a run, definitely make it simple for you both to do what you need to do and then come back together for dinner. It’s just life.

6. Talk money ASAP.

Talking about finances in a relationship can be weird in general, and for many people it’s a major point of contention. But generally talking about money upfront is always better than waiting out of fear and then having a more awkward conversation later. If one person can afford a lot more maybe they’ll be willing to put in more towards the trip. Maybe they won’t be at all.

Figuring out where you both stand on that and then deciding what sort of a budget you can agree on is crucial. You want to be able to relax on a trip, not have an anxiety attack every time she suggests calling room service. Make those decisions ahead of time so that there aren’t any surprises or a terrifying conversation to dread in the near future.  

7. Don’t second-guess the decisions you make.

When you’re both hoping to have a good time but also hope that the other person is having a good time, it can be easy to get caught up in second guessing every single decision that you make. She let you choose the restaurant but now you’re worried that she doesn’t like it enough, that sort of thing.

If you second-guess everything the whole time you won’t be able to relax and have any fun, so try to let go of the worry unless there’s an actual issue that you’re dealing with. If she isn’t happy with anything maybe there’s something else going on. If she’s happy to be with you she’ll probably be happy doing anything.

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8. Don’t freak out if the sex situation is different.

Depending on what sort of trip you’re on there might be a lot more sex than normal, or there might be none at all. Camping under the stars in a small tent sounds cozy and romantic in theory, but it can also be suffocating and filthy. If things are not as hot as normal don’t worry that the spark is gone, it might just be the trip. And if things are hotter than normal don’t be dismayed when you head back home and the passion drops off a notch.

9. Be mindful of bathroom time and other personal habits.

Some couples are quick to open up about what goes on behind closed bathroom doors, and some couples never ever speak of it ever. Depending on how much time you guys have spent together, she might not have ever been in a situation where she’s even had to do her makeup in front of you let alone handle her toilet business. Talk about potential stress for a lady.

Unless she’s super open and comfortable about that sort of thing it’s usually a good idea to give her some space to do what she needs to do without questioning or micromanaging it. And hopefully she’ll do the same for you. Sometimes when you spend a lot of time together for the first time you start to find out weird things about people’s personal habits that you were unaware of before. Maybe she wears a retainer in her mouth when she sleeps, or perhaps she leaves her underwear on the floor. Those aren’t tragic things at all, they’re just new to your life, and new can be a little scary.

Plus, something that seems weird to you on a trip might not be weird at all at home. If she has to check her work email at a certain time each day or something it can be a little annoying when you’re trying to run out the door for a scuba lesson, but at home on an average day you wouldn’t even notice that.

Whatever you do don’t freak out about the little things. Being close to people requires a lot of new things, but the small ones aren’t the things that actually matter when it comes to what you like about who they are.

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