My wife’s father used to insist when she was growing up that before she got married to anyone, that she needed to take a Greyhound bus trip across the United States with them. That would put enough strain on the relationship to see whether a marriage made sense.
Fortunately that was advice meant to weed out the suitors they did not approve of, and her dad didn’t press for us to do this. I never wanted to take the Chinatown bus between New York and D.C., much preferring one of the Northeast shuttle flights (I mind Amtrak less now than I did 20 years ago, since I bring my own wifi with me rather than relying on theirs – seriously, it’s bizarre that even airlines with the worst wifi at 30,000 feet have better performance than Amtrak does on the ground).
However, the advice to travel with someone to weed out incompatibility quickly, and get a true understanding of someone you’re dating really does generalize. I noticed an Instagram reel making this point, and it’s really worth teasing out the reasons why.
So as soon as you start dating somebody, they’re going to be putting on a show of who they want you to think that they are. So I think it’s so important, as fast as humanly possible, when you start dating somebody, you need to go on a trip together. Like, not like a crazy trip, but maybe like a weekend trip. And so when you and I started dating, like, what was it, three weeks into dating, we went on a week-long trip to Cancun?
Because then you get to see how they actually are, how they participate in new environments, your out of your comfort zone. You know, again, like you’re not doing anything crazy, but it could be just like a little weekend getaway, but you get to see who they really are. And then I just know couples that were dating for months and months and months, sometimes years, they go travel together and they freaking hate each other. So it’s a really fast way to be able to determine if you’re compatible or not.
When you travel you see all of a person, not just who they want you to see. And they reveal their character and ingrained behaviors.
- Stress response: missed connection, delay, lost bag, bad room, do they problem-solve or do they blame and find themselves helpless?
- Treatment of service workers: gate agents, flight attendants, hotel staff, it’s tough to maintain fake politeness in unfamiliar circumstances.
- Beliefs about money: who pays, tipping beliefs, impulse purchases or resentment over upgrades and nicer meals?
- Planning style: Are they meticulous or do they wing it? Do they adapt their planning style to reduce the burden on their partner?
- Punctuality: how do they think about time? When do they show up at the airport? When do they wake up? And on the subject of waking up, what’s their mood, coffee habits, bathroom habits, and grooming?
- Behavior when super tired? Long travel days can bring out irritability and neediness that they might hide on even a longer date in town.
- Decision-making style and compromise: where to eat, what to do, how much to spend are insights into compatibiltiy.
- Cleanliness: do they leave the hotel room a mess (and do you?) and what are their bathroom havits and packing style – carry-on only or checked bags, fresh clothes or re-use?
And these are just a few areas where people reveal themselves. And I think the really extended conversation without break is important too. I’ve long thought one of the most important ways to think of a marriage is as a fifty year conversation. Do you actually want to keep talking to this person? Do you find them endlessly interesting? Not to mention are they someone who makes life easier or harder?
There’s no better way to get to know someone deeply, where they truly reveal themselves their behaviors, than traveling with them.


Great article Gary. And so very true.
I vacationed with my future wife 14 times (including Mexico, Africa, Europe etc. before pulling the pin. I mean, popping the question. A little extreme perhaps but It saved me from the same fate as my previous two marriages.
You know, that is really good advice. Maybe the honeymoon trip should be before you tie the knot! Actually I think you can learn a lot about somebody by watching how they drive. Do they use good judgment or do they tend to be overly aggressive? Courteous in traffic and to pedestrians? Keep a careful lookout for potential problems? Get distracted easily? I’ve been traveling with my wife for over 50 years and while we negotiate our plans, I’m still surprised by how spontaneous she can be. I hope that never changes.
Perfect post, Gary. Laughing! My professional life until I retired at 77 in 2024 often involved weekly travel, for 50+ years. I was good at it. (My first flight was before I was 1 on a prop plane from Ohio to NJ to meet my other grandparents.) Because my work was in a travel/hotel adjacent industry segment, my knowledge of and appreciation for the workers and work allowed me to be patient. What I learned early on: I get into a “zone” and travel well solo and not with others – be they friend, client, or spouse. My marriage has lived well with me at home – that was our test and COVID lockdown the trial “trip.”