Dating When Living In Hotels

Filed Under: Travel

As I’m approaching the 18 month mark of living in hotels, one personal question I’m often asked is “how do you date if you’re constantly traveling?” While I’m perhaps an extreme example by living in hotels full time, I think the general struggle of dating while being a frequent traveler is something many can relate to.

So without getting too personal, I figured I’d address the topic in general, because it’s something I’ve learned quite a bit about.

How do I date while traveling? I don’t

For me the answer is perhaps a bit anti-climactic. I’m an introvert to begin with, so am not someone who needs to go on dates to feel fulfilled, or whatever. I’m generally pretty exhausted due to all the timezones I transit, so I’m just as happy going to bed at 7:30PM on a Saturday as I am doing anything else.

I also believe “a watched pot never boils.” In other words, I’m still fairly young, and am in no rush to force any sort of a relationship. I figure if the right relationship comes along, great. If not, that’s fine as well. Having been in a long term relationship, I’ve known I was in no rush to repeat that. At the same time, long term I’d love to have a home and a dog, and only occasionally get on planes.

The curse of the traveler

About a year ago I shared a comment left my reader DJ, entitled “The Curse Of The Traveler.” I’ll share it in its entirety again, because I think it’s really, really profound:

An old vagabond in his 60s told me about it over a beer in Central America, goes something like this: The more places you see, the more things you see that appeal to you, but no one place has them all. In fact, each place has a smaller and smaller percentage of the things you love, the more things you see. It drives you, even subconsciously, to keep looking, for a place not that’s perfect (we all know there’s no Shangri-La), but just for a place that’s “just right for you.” But the curse is that the odds of finding “just right” get smaller, not larger, the more you experience. So you keep looking even more, but it always gets worse the more you see. This is Part A of the Curse.

Part B is relationships. The more you travel, the more numerous and profoundly varied the relationships you will have. But the more people you meet, the more diffused your time is with any of them. Since all these people can’t travel with you, it becomes more and more difficult to cultivate long term relationships the more you travel. Yet you keep traveling, and keep meeting amazing people, so it feels fulfilling, but eventually, you miss them all, and many have all but forgotten who you are. And then you make up for it by staying put somewhere long enough to develop roots and cultivate stronger relationships, but these people will never know what you know or see what you’ve seen, and you will always feel a tinge of loneliness, and you will want to tell your stories just a little bit more than they will want to hear them. The reason this is part of the Curse is that it gets worse the more you travel, yet travel seems to be a cure for a while.

None of this is to suggest that one should ever reduce travel. It’s just a warning to young Travelers, to expect, as part of the price, a rich life tinged with a bit of sadness and loneliness, and angst that’s like the same nostalgia everyone feels for special parts of their past, except multiplied by a thousand.

I’ll let that quote speak for itself, because I think any frequent traveler has felt this curse. It’s awesome… and it sucks…


Oh crap, now I am dating…

The funny thing is that I met someone great shortly after I realized I didn’t really want anyone. I guess that comes back to the “watched pot never boils” mantra. So I couldn’t be happier with him, and it’s sort of odd to date someone who doesn’t know the first thing about miles & points.

Perhaps it’s a good topic for a future post, but I can’t begin to say the amount of satisfaction I’ve gotten out of setting up frequent flyer accounts for him, requesting missing mileage credit for the flights he has taken in the past, etc.

So how does having a boyfriend work when you live in hotels full time? Based on past/current experience, what I’ve learned is the following:

Explaining you live in hotels can be awkward

When I was in high school and took mileage runs on weekends, I didn’t bother explaining to friends what I was doing. Because it seemed like more trouble than it’s worth.

Similarly challenging is explaining to someone you potentially want to date that you live in hotels full time. Because that’s not normal. Like, at all.

When you say “I’ll pick you up at 6” and pick your date up in an Uber rather than your own car, or when you actually legitimately invite them to breakfast at a hotel because it’s included (no strings attached), well, it sure can be a conversation starter, if nothing else.

Hotels can be a blessing… and a curse

When you have a lot of schedule flexibility and date someone who has a “desk job,” it can be a blessing and a curse. On one hand it’s great that you can travel fun places on weekends quite easily and create memories. On the other hand, it does set a tough precedent for the future.


Constant vacations aren’t a stable start to a relationship

Along similar lines, spending most of your time together at first in hotels doesn’t necessarily tell you whether you’re actually compatible. Anyone can have fun together traveling to a fun place, but how about if you’re just sitting at home and being lazy on a Saturday and watching Real Housewives while eating Chipotle (which sounds like heaven to me, but…)?

Moving somewhere is a lot of pressure

Perhaps this is the biggest struggle. If you’re dating someone, at some point you’ll want to move to a city to be with them. At the same time, ideally you’d move to a city independently of the relationship you’re in. Because that adds a lot of pressure to a relationship to both parties.

I’m very fortunate in this case, since I’ve been thinking of moving to Los Angeles for a while now, before I met my current boyfriend. And he happens to live there, so it works out quite well. But in general that’s certainly an issue.


Bottom line

I’m sure I’m not the only “road warrior” who struggles with dating, and I’d certainly be curious to hear about everyone else’s experiences. The challenges will of course differ depending on the circumstances of the relationship and where someone is based, though I think there are some common themes for all frequent travelers.

Just to clarify, I couldn’t be happier with my current relationship (like, actually), but these are some general things I’ve learned over the years, and I’ve tried to adjust my behavior this time around as a result.

How do other road warriors handle dating?

  1. Ben came out! Good for you!

    But yea, I agree with much of what you said and especially the quote. I’ve had same thoughts in fragments, but the quote was very well put. I want to travel the world while I can (easiest when I’m single), which sharply contradicts with how I often feel on the trip to want to witness the greatness before me with someone important.

  2. @Endre: +1 😀 What I can tell you is good escort companies does accept credit cards so you can earn some miles while you …. 😉

  3. It’s not the same exact situation, but I met a girl and fell in love with her while we were living across the US from each other. Now she’s a grad student, and still half a country away.

    I’ve had to get used to having a different kind of relationship. One with hotel stays and joint trips to a third city. We spend a lot of time using FaceTime or google hangouts while just working quietly, occasionally saying something to each other. I don’t think I could ever do a casual relationship this way, but she’s worth it.

    Actually this girl is why I’m on this site. I never was interested in miles and points as a hobby, but I’m probably booking 25-30 plane flights a year now, (girlfriend and work) so it pays to be on top of these things.

  4. Well, this is certainly a development! Congrats Ben on meeting someone special. I laughed at you having to set up mileage accounts and explain the way points work. (Just remember to talk about other stuff too occasionally…. ;-p)

    Does he read the blog or is too early to reveal yourself to him through all the back posts? (pretzel rolls, germ-phobia, Krug, #top…) 😉

    Did he meet the folks yet? (Ze important zing Benny ist to be happy…)

    Thanks for sharing this personal news. Truly excited for you!

  5. Ben, I have a serious question! There’s a video with you where you’re talking about a seriously scary flight from BKK to HKG. Is there a blog post about it? What happened?

  6. “Constant vacations aren’t a stable start to a vacation.” Are you kidding me? How can you possibly say that? Look at how successful they’ve been with the Bachelor series! 😉

  7. @Thanh, Ben came out a long while ago when he had those pictures in Africa of the tent hotel and he was with a male friend and there was only 1 bed in their room.

    That said the Old Guy has a point, the more you travel the more cultures and girls or guys you meet and you start liking each part of each culture and then dating can get even harder.

  8. @tanh

    This is hardly a coming out story.

    I find that travel is manageable in a relationship provided communication is clear. It takes real work, but it can work out well.

  9. Great news Ben!
    In your post, the following quote stood out for me: “I figure if the right relationship comes along, great”

    I applaud you for not ‘searching’ for love, but letting it find you. I know it might still be early, so take ‘love’ with a grain of salt. Regardless, living your life and not forcing yours to be like everyone else’s is wise. This is from experience, as travel brought my husband and I together. We met in an airport and lived 4,000 miles apart. This was before FB or really even email. By phone for 6 months before we co-relocated to a place in between on the West Coast.

    Enjoy getting to know each other and the satisfaction of introducing him to your hobby and hopefully you’ll likewise enjoy getting to know his hobbies, etc.

    Oh, and as much as you might take him home to visit your folks, don’t forget to bring him by the Blog here to introduce him to your ‘work family’ here. We have to approve ya, know!

    Kidding!!! To the contrary – keep it private unless you both feel it’s time to do differently. Cheers to you both and hope for the best!

  10. There was a thread on Reddit about how points have changed your life. It got me thinking about the positives and the negatives but a lot of it resembled the sentiment of the curse of traveling.

    I did point out that it negatively affects my relationships as a whole. I find it harder to make solid friendships or start dating. The way I see it, and maybe it’s this is just an excuse, but the more you travel the more it becomes a part of who you are. The more it becomes a part of who you are the less people who don’t travel can relate. The stories you tell are about adventures Tokyo, London, and Rio. Your pictures are from the beaches of Bali, the canals of Venice, and country side of New Zealand. No matter how hard you try most people will see all this as bragging (to a certain extent it is but not as much as it comes off as). Less time is spent in hobbies you can do around your drivable area. You invest less in regular meetups and events because you’re schedule is really unpredictable.

  11. It can be tough. My last relationship was with a woman who couldn’t have cared less about points or miles or international travel, really. It’s funny how you can be willing at first to meet someone halfway, even on the things that truly drive you. But eventually the fissures grow bigger. It got to the point where I really resented going the extra mile (see what I did there) to ensure she flew with me in F, we stayed in nice hotels, etc., because it obviously didn’t matter that much to her. On the flip side, when I was alone and halfway across the world, it was nice to know I had someone to come home to.

    I think so many of these things just come naturally as you get older. You live and you learn. With luck, you find someone who understands the life you either have to live or choose to follow. And in return, you compromise, adjusting yourself to complement that person and their lifestyle.

    That said, on my last date a very lovely young woman mentioned her allegiance to DL and I threw up a little. Some things will never change.

  12. Ben; Love happens when you least expect it; but maintaining a relationship, like a garden, takes work and constant nurturing. Congratulations and Mazel Tov. Oh, did I forget compromise?

  13. I always thought you collect the “rubber duckies” and Hello Kitty stuffs to impress gals…boy was I wrong! hehehe, just kidding. I noticed hints on the blog and from viewing your interview videos.

    Congrats for making it official and take the guessing work out. Happy that you found someone!

  14. @pavel: “a very lovely young woman mentioned her allegiance to DL and I threw up a little.”

    ^^ owes me a keyboard…

  15. Happy for you! My husband and I make great memories traveling together and I think for many people-travel is stressful so you see what people are made of and if you are “travel-compatible”. And LA is awesome. It’s still fun to come home after being away 🙂

  16. It’s funny. I traveled 300K+ miles each year for a long time and my husband and I managed to figure out a routine. Now I’m around 150K miles each year and it seems like I’m standing still. He’s always asking, when are you traveling again? Absence makes the heart grow fonder and it’s worked well for us. That quote is profound and very true as the desire to travel just keeps getting stronger even after having been to around 50 countries.

    I have read your blog for years and I am very happy that you have found a boyfriend. I met you once early AM in the Club Lounge of the Sheraton at FRA. This was long before the Rolling Stone article or the TV appearances. I got the sense that you were lonely at that time and I’m glad to see that you’re now opening up and dating. Wishing you the best.

  17. Wow, DJ’s words are incredibly profound. It is both awesome and it sucks.

    I’ve been traveling most of my adult life, domestically for work, internationally for fun. I took forced break during the economic downturn in 2009/2010. Settled down, bought a house, got a dog, met someone and we moved in together. It all seemed perfect, but a tiny voice kept trying to pull me back to the road. Eventually I gave into the voice, quit the desk job and started traveling again. This caused strife in the relationship leading to a breakup.

    I’ve fallen into a pattern of working about 30-35 weeks a year, traveling every week in the US. Then the other weeks I travel internationally, mostly with one particular friend. Our friendship will be nothing more than that, we are incredibly close but since we live in different cities we essentially only see each other when we travel abroad about 4 times a year. I have some friends I go out to dinners with and do things when I’m in my home city, but I am mostly content to enjoy a nice glass of wine catching up with tv before going to bed early on a Saturday night.

    DJ’s words could not be truer. I’ve found myself in that state that no one place satisfies me, no one person does either. But am I lonely? No, actually, I’m not. My travel absolutely fulfills me…each new person I meet, each new place I go to just adds to that richness of my life. I meet people who consider my lifestyle a curse, but I have experienced theirs and was more miserable than I could imagine.

    I wish you luck with the relationship, I sincerely hope it becomes what you want it to be. I however, will be forever married to the road, and the road is always there for me.

  18. You can always spot the rookies on the site once they post 🙂 “out in whatever” just keep doing what you are doing and be happy

  19. I think the curse of the traveler is actually why there is so much value in travel as a family. We have three young kids and I know a lot of people may think we are crazy for doing the types of trips we do but they will connect us in a way that staying home can’t. We will always remember riding an elephant in Thailand with our oldest or sweating it out in Rome when we just had two. Now, my kids are at an age where they will really start to remember and I can’t wait to hear their sides of the travel story as they get older.

  20. Glad to hear you’re in a good relationship! From this old guy, just remember to keep your own identity. My partner (soon to be husband) have been together 19 years and what we most love about each other is our individuality.

  21. Good for you Benny boy! Currently working through a relationship that has turned long distance due to work… It’ll be great that you’re both living in LA!

  22. Strange the folks that think been is coming out. He’s been “out”. For like, quite a while that I’ve been reading this blog. But congrats, Ben. (I was kinda hoping it was Matt, but the twin beds did throw me, LOL).

  23. I met my husband while I was a road warrior. He lived in Hawaii and I lived in California. This was before there were cell phones and regular long distance calls cost a ton of money. We talked a couple of times a week and he wrote me a letter every day. I still have them. After a year, he moved, we married, are still together, and celebrated our thirty three anniversary this past week.

    I traveled my entire career, am now retired, and I still travel both with (about a quarter of the time) and without him. You can maintain individuality and have a great relationship whether you travel together or not by making the other person the most important thing in your life.

    Also, I never believed in love at first sight – too practical, too introverted, and too grounded. Well, I was wrong.

    Wishing you all best to you and your friend.

  24. For all those congratulating on coming out, apart from the fact that it was really obvious, and I don’t have a feeling Ben was trying to hide the fact he is gay, it is just plain silly. Coming out is not a thing that needs approval or congratulations, except if one is seeking attention.

    As for the “who is he”, it is easy to find the significant other just browsing this page. 😉

  25. That “it’s better not to even tell your friends what you’re doing” is so true. I’m a junior in high school and when I go on mileage runs or non-rev trips it’s so hard to tell my friends and even extended family that, that’s what I live doing. I always get some crazy-death stare like “Jesus you’re insane, air travel is the devil”.

  26. Lucky, I’m glad you have found someone. Maybe he can help you get over your, what appears to be, harmful obsession with Real Housewives.

  27. I just got good news that I’m lifetime Platinum SPG and have 100+ nights to renew my ambassador. The bad news is I’m lifetime Platinum and have an ambassador. Business travel has not been great for my relationship. My travel is a function of work, with a few joyful travel events here and there. But I’m not loving spending endless nights facing the same hotel menu without my Mrs. I grow tired of packing up, leaving bags, dealing with dry cleaning, figuring where to eat, fire alarms, plane/train delays, surly cabbies, expense reports, etc. Not to mention trying to stay healthy and avoid all pitfalls of the road (overeating/drinking, no exercise, loneliness, missing family events)
    Sure I enjoy visiting places with the use of my points for leisure but the stress work travel has placed in my life, I’d give it all back. Good luck dating.

  28. Well, I don’t think a lot of you understand what “coming out” means. It’s basically making it official. There could be hints, hunches, and what not (and regular readers saw them), but unless it came directly from the person himself, it’s not considered coming out…

  29. Just a note to say this is one of the best posts I’ve ever read of yours and I’ve been reading for quite some time. Great job!

  30. I too am entertained by the “you’re finally coming out!” post, since the article in Rolling Stone in July explicitly said so, and I’m pretty sure there’s been mentions of that before that. With that said, congrats – and good luck. Having been in a long distance relationship myself for the past several years, it is hard. We visit several times a year, but my obligations as a grad student and his to his job keep us apart. The internet is a lifesaver.

  31. Oh here is the reason why I’ve been finding lucky’s posts outstandingly gay on this site. Haha no offence, just that my intuition was sharp…

  32. Mazel Tov Ben – you cannot rush or force the moment when Mr Right comes into your life. My experience is that it happens when you least expect it to. That was 22 years ago for me.

    Communication and Laughter are the keystones to a long lasting relationship, with a big dose of compromise too.

    My husband is my best friend, may your boyfriend become your best friend too.

  33. A slightly different take on living with a road warrior. My husband and I have been married 34 years and he has traveled enough to be a delta two million miler with every single mile earned flying in the United States. Unfortunately, he flies and stays in hotels for business so much that the thought of getting in an airplane and staying in a hotel for vacation just does not appeal to him. Thus, we either take day trips or we try to find a bed and breakfast. I do go on the “fun” business trips and he can usually get away for a couple of hours of sight seeing. So we don’t usually get to see anything but the highlights of a city but we’re not paying for the hotel room and I haven’t had to pay for a plane ticket in forever. It’s all a lifestyle based on what job you have, I suppose.

  34. It’s rare you get personal and as a reader from the early days it’s good to hear these things every now and then. Excited for you!

  35. Congrats!! Can’t wait to hear later posts now that you’ve got some love in your life!

    “How to use miles to fly both sets of parents in for the holidays”
    “Using points and miles for a destination wedding”

    LOL at the people who are congratulating Ben for “coming out”. He was never “in”.

  36. This was my favorite post of the year, hands down. Thank you for sharing important stuff with us! I think your professional success is well-deserved, and while none of us earns happiness in our personal lives based on merit, it is certainly delightful when one of the “good guys” finds a special someone to pursue that happiness with. Best of luck for you and your fella.

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