7 Questions to Ask Before You Travel Together

Having good travel chemistry with someone can elevate a trip like nothing else. The flipside? If you aren’t navigating from compatible objectives, it can break your experience. I learned this the hard way: years ago, on a trip to Thailand, my travel buddy abruptly decided to fly home early — hardly a day after we’d arrived. I’d bought my ticket to Bangkok on his request, as an extension of my own pre-existing plans; he said it would mean a lot to him if I’d join him for those dates. Imagine my stupefaction, thus, when he made the following declaration from our rented hostel room, chuckling as if he’d just had an earth-shattering personal epiphany:

“IIIIII don’t have to tell people I was on the beaches of Thailand!”

As in, he was at peace with the idea of ending the trip early because he had suddenly realized that he didn’t need the bragging rights. I let my shock reverb for a moment before I asked: “Is that what it was about for you? Being able to tell people you went there?”

Yes, he admitted; a huge draw for him was about trying to impress.

Had I known the guy didn’t have an authentic interest in our destination, I’d have planned very differently. Instead, I lost heaps of money.

How can you avoid nasty surprises like this? Asking the right questions ahead of time will prevent you from making faulty assumptions that end in busted plans, wasted money, and other big disappointments. Here are those questions — along with a few anecdotes to illustrate why they matter.

1. How much does ego factor into their decision to visit this place?

As per my Thailand story, some people want to be able to say or show that they’ve been somewhere — for the clout, the status, and the likes. Others want to actually go there — for the culture, the beauty, and the vibe. People won’t usually admit to being shallow, so you might not be able to ask them this directly. But think: how invested is your companion in questions of image and/or affluence?

For instance, my Thailand-trip friend had mentioned on various occasions prior that he had a history of trying to cultivate an image of clout. Somehow I didn’t think this would affect our time together. I was way wrong.

If you’re primarily about exploring and experiencing, while the other person is mainly into peacocking and posing? Proceed with caution.

2. How open are they to engaging with the local culture?

Once upon a trip abroad, a companion wanted to make frequent stops throughout the day, most days, for an hour or two at a time, to nurse a blended-ice drink… almost exclusively at places like Dunkin and Starbucks. This surprised me, but I obliged. Still, I would’ve rathered wander around (with a drink, if he needed one) and stop at local eateries to rest — so that we could immerse more in the culture rather than, you know, spending half of any given day at a series of Starbucks. Alas, when I proposed trying to steer away from a US-culture bubble, he got angry. Our preferences didn’t align.

Before you book a ticket, ask: will your companion be game for long hours of wandering in order to soak in the place, or do they need (for health reasons) or prefer (for reasons of personality) a rigid itinerary? Likewise, are they interested in eating all or most meals where locals eat, or are they only comfortable in international chains and slick tourist traps? No answer is wrong, but your answers should ideally mesh.

3. What kind of rhythm will they want to maintain?

Crazy story, but many years ago, I traveled with someone who had extreme needs for sleep… and unusual quirks regarding water. I would’ve been content to leave in the mornings to explore by myself and just meet up in the afternoons when he was ready. There was just one problem: he got upset if I was the first to shower or boil water on any given day. Frustrated that I didn’t want to wait around in the room for him until lunchtime — unshowered and dehydrated — he tried to persuade me that vacations should be about rest, not activity. Alas, my priority in being abroad was to experience the city, not the room we slept in. So our daily rhythms were fundamentally at odds… which sucked.

Ask your companion: are they looking forward to this trip primarily for exploring or for R&R? How about their ideal daily schedule: how late do they want stay up or sleep in? Most importantly, are they sincerely okay with you doing your own thing when they’re tired (or vice versa)? If they’re not fine with you being independent for small bites of time when they just want to sit it out, that’s a bad sign. Find out in advance.

4. What’s their approach to expenses on this trip?

You MUST discuss your respective standards for things like lodging, transportation, and food. What sort of places would they prefer to lodge in: how central or fancy (or not), and for what price? How do they prefer to get around: trains and buses (cheapest), cabs (variable), or rental cars (most expensive)? As for food: what’s their daily budget, and the cost of any special meals they hope to try?

Those are the basics. However, above all, you should talk openly and honestly about what kind of price tag strikes each of you as a “splurge” vs. a “normal” expense — and what you’re each willing to splurge on. For instance, if $10 is a pricey lunch for you, you’d probably rather spend those $10 on food you’re stoked about, rather than, say, a boring burger in a tourist trap… whereas $10 for bland food might be a total non-issue for them. Money questions are tricky. See “How to Travel With Your Poor Friend” for more pointers.

5. How will they handle seedy offers?

This is critical; it pertains to safety. Some places have famous scams whereby an organized group extorts an exorbitant sum in exchange for a cultural experience, an artwork, or a game. Alternatively, some people try to sell off-the-books antiquities (which is unethical whether the item is real or not… and can get you into serious trouble if so). And in some locales, the consequences for being caught with or in the vicinty of controlled substances are downright draconian, so a friend’s decision to use — even if you don’t — can ruin your life.

It’s scary when your companion isn’t on the same page. I know this from experience. Once, a friend let a rickshaw shuttle us straight into a classic scam setup and got angry at me for trying to protest. He later admitted that he’d sensed it was a scam too, but that he wanted to dip his toes in, in order to prove he could control it; while it was just an ego game for him, it could’ve cost me tremendously. Likewise, one companion purchased a supposedly-ancient clay vessel in a foreign city, despite my trying to discourage an illicit trade in cultural patrimony. Was it a fake? If so, he got scammed— and if not, he’s very lucky he wasn’t arrested.

In any shifty situation, your safest bet is to say no and quickly get FAR away. Research scams at your destination, and inform each other so you can both be prepared. But have a Plan B up your sleeve in case your travel buddy opts to flirt with danger; that way, you don’t have to get dragged into it.

6. What are your respective intentions regarding vacation hookups?

You don’t want someone spewing negativity all over your trip because they’re sexually frustrated or jealous. You also don’t want anyone getting ditched at a vulnerable moment in a far-flung place just because the other person can’t control their urges. So talk this stuff out far in advance and decide how you’ll approach your nights on the town together — or apart.

My story? A guy friend once sprang it on me while on vacation that he’d been wanting to use our trip as a chance to get laid… and therefore saw me as an inconvenience. Namely, he griped about how much attention men gave me without my trying; he felt guilty about ditching me, he said, when so many men were waiting to pounce — but he simultaneously felt frustrated that women wouldn’t approach him if he was near me. I was stunned; I was personally fine with forgoing sex during our travels, but I had no idea he wasn’t fine with it — and I would’ve made different plans if I’d known.

Will you (or your companion) actively look for love? If no, what will you do if someone unexpectedly meets a compelling stranger? If you are looking, will you play wing(wo)man for each other, or will you search solo? Likewise, if one of you gets lucky, where will you go to hook up, and how will you communicate your new evening plans to your travel mate? If you talk this out in advance, no one will be left feeling aggravated or snubbed.

7. What happens if one person makes a questionable friend?

Part of the fun in travel is the people you meet along the way. And when a new friend enters the group and everyone gets along, it feels like absolute magic… but if your buddy teams up with someone you don’t trust? This will drastically compromise the quality of your experience — and maybe your safety, too.

This happened to me once: a friend started hanging out with some guy from his hostel. The new guy seemed cool on the surface, but in moments when my back was turned and no one else was paying attention, New Guy touched me inappropriately. I expressed my concerns privately to my friend, but he didn’t like hearing that I distrusted his new bro. Long story short, the way my friend handled the predatory new guy — taking issue with my discomfort and even then placing a female friend of mine at risk of assault — burned up my remaining trust in him.

Even though my friend was traveling, I had an advantage; we were in my city, so I was able to keep a distance from New Guy much more easily in order to stay safe. But travel leaves you vulnerable. So make a pact that you won’t force interactions with, much less compromise each other’s comfort for, a new “friend” you don’t agree on. You can spend time apart on the trip to create space for new connections to bloom, but you should still honor the reluctant party’s desire for boundaries. And if your travel buddy downplays your concerns and violates the safety-related boundaries you’ve requested? Maybe you should think twice about your whole relationship; anyone who unapologetically gambles your safety is unworthy of your trust.

Travel can always generate scenarios you weren’t planning for, but asking questions like these in advance can prepare you to navigate each other’s needs in a way that leaves you both feeling like your investment in this time together has been worthwhile. You don’t have to be on the same page about everything in order to have a fantastic trip. But having compatible priorities — or discovering in advance that you don’t have compatible priorities and thus deciding to hit the road alone — will make your adventure that much better.

Do you have other questions you like to ask a prospective travel mate? Feel free to share!