Okay, despite all the websites and books that tout solo travel as a wonderful way to see the world, let’s say you’re not quite ready to travel alone yet. You want to get your feet wet just traveling at all, but alas, you’re single or married to a homebody and you just don’t have an obvious person to travel with. So you rack your brain in desperation, trying to think of someone, anyone you know who might be willing and able to go with you. There’s always Sally in the office who talks about wanting to get out of the cold Northeast to go to Florida or somewhere warm. Or what about your cousin Dave? The two of you have always gotten along great at family gatherings, he’d be fun to travel with. Maybe your best friend’s spouse will watch their kids for a few days while the two of you head to Atlantic City for a wild weekend. Stop right there.

Before you issue an invitation to travel with you, keep this in mind: Unless you’re rolling in dough and free time, chances are, you are going to have limited vacation time and a limited number of trips to take each year. Do you really want to ruin your vacation by choosing the wrong travel companion?

But what’s wrong with Sally or Dave or your best friend, you ask? Just this: Have you ever traveled with them before? If not, then you could be taking a huge risk. Just because we get along well with someone in our everyday lives doesn’t mean they will be a good travel companion. People’s travel styles vary widely, and unless you know about it ahead of time, your best friend could wind up being your worst nightmare by the end of your trip. Annoying habits that you normally overlook in someone become magnified a thousandfold when you are with them twenty four hours a day for days on end.

How can you find a good travel companion, then? The same way you find a good employee, or a good dogsitter, or a good anything. You interview them. Or rather, you interview each other. A few years ago, one of my friends expressed interest in coming with me on one of my trips to Vegas. I was excited about this, because I thought it would be fun to have someone to show “my” favorite city to. And we always got along great. However, as a single (and an introvert) who had lived alone for many years, I recognized that I wasn’t used to being around someone else for 24 hours a day, and I could foresee the potential for disaster if we weren’t on the same page. So before we agreed to take the trip together, we got together over coffee and went over some questions so we could identify our own travel styles, budgets and needs, and see if they meshed. We also negotiated certain aspects of the trip ahead of time. By the time we took the trip, we both knew what to expect from each other and were very satisfied with the vacation.

If you’re not sure what to ask a potential travel companion, here are some questions to get you started. Ask these questions of yourself, too. It’s important that you understand your own travel style so you know if your companion’s will be compatible. You may find that only some of these questions are applicable to you, or you may have others about things that are important to you. The point is, be very clear about what you expect from a vacation and what your potential companion expects. If during the trip your companion violates an agreement you made prior to the trip, don’t hesitate to bring up the ground rules again. Or if some issue arises that you didn’t anticipate (and inevitably, it will), talk it out immediately. It would be extremely rare for two people to agree on every single issue, so be prepared to compromise. (Or reconsider traveling alone.)

And if I may offer some advice, I think it’s really important to build in some solo-time to your trip even when you do have a travel companion. If the two of you get a breather from each other once in a while, you’ll appreciate the time you are together that much more. Plus it’ll show you how much fun you can have doing things on your own in a new place and it’ll build your confidence that you can indeed plan an entire solo vacation sometime in the future. Maybe your next trip, in fact.

Travel Compatibility Questions

1. Once you’ve agreed on a destination, the first consideration is your individual budgets. Are your budgets and tastes compatible? If one of you wants to rough it out in a hostel while the other wants to experience 4 star hotels, you’ve got a problem. Are you willing to split a meal to save money if the portions are large (and in the U.S., they almost always are)? What sort of a dining budget for the trip do you have? I recommend being blunt up front about what your budgetary restrictions are for this trip.

2. If you are flying to your destination, what is more important to you: Cost of flights, convenience of flights, or flying a particular airline? Are you willing to take different flights from each other and meet there?

3. Are you a planner or do you prefer “winging it”? It’s not so bad to differ on this one, actually; two control freaks trying to plan the same trip may find themselves butting heads a lot. Two people who fail to plan ahead might be disappointed that the attraction they were so interested in seeing is closed on the only day they could go there.

4. Are you comfortable sharing a room with someone else or not? Are you a night owl or an early bird? Do you snore or suffer from night terrors/walk in your sleep? Any other weird nocturnal habits you’d rather no one else know about? Snoring can be a dealbreaker, trust me.

5. What do you hope to get out of this vacation? Sightseeing? Relax and get away from it all? Shopping? Museums? Nightclubbing? I recommend each person jot down all of the things they want to do on the trip, circling the top 3-5. Compare your lists and make sure each person gets to do their top 3-5, even if it means splitting up for part or all of a day. If you have NO items in common on your “list of things to see and do,” chances are, you really aren’t going to be compatible travel companions.

6. Are you an introvert or an extravert? If you don’t know the difference between an introvert and an extravert, ask yourself: Do you prefer to be around other people every waking hour, or do you need “alone time” every day? The introvert needs alone time every day. Along the same lines, are you a positive person or a negative person? Someone who complains a lot can be a real drag to someone who is generally upbeat. Are you a nonstop talker, or do nonstop talkers drive you nuts?

7. How independent are you? You may want to do your own thing in the day and just touch base for breakfast or you may want to share all of your experiences. Talk it out up front! If it would drive one of you batty to have someone stuck to you like glue for the whole trip, you need to find out before you go!

8. Do you have compatible life habits? Do you smoke? Is one of you a vegetarian? Are you a heavy drinker (3 or more drinks per day) or drug user? Do you have any potentially dangerous habits? Allergies or aversions to strong scents? Phobias?

9. Are you comfortable and/or willing to drive in a strange place?

10. Are you looking to hook up with someone sexually on this trip? If one or both of you are, and you’re sharing a room, you’ll need to negotiate use of that space.

11. This one is SO important: Negotiate ahead of time how shared expenses (such as hotel, cab fare, etc.) will be handled. If charges such as parking, phone, Internet, pay-per-view, cabana rental, spa or room service will be part of your hotel bill, be sure to negotiate ahead of time how those charges will be split. You don’t want to agree to a 50/50 split and then wind up paying for half of your roommate’s $100 call home to her boyfriend.

One last piece of advice: Once you have found a suitable travel companion, be sure to exchange emergency contact information as well as information about any potentially life-threatening medical conditions, just in case.