Dating and Travel

Traveling and exploring new foods, dances, lifestyles, and religions outside of my own is a core part of who I am. I’m always thinking about the next adventure. This is why any guy who tells me he doesn’t like to travel is automatically not a match, and I’m grateful when that happens. It saves us a lot of time and money. This is also why I like to travel together early on in the relationship (within the first few months). In fact, it's become so important to me, that I really don't start having real attachment or consider us serious until after we travel together. Now, I'm not saying book Bali together the day you meet, but a simple weekend getaway can reveal a lot.

When I lived in Chicago, my then-boyfriend and I drove to DC for a few days. It was enough for us to see each other in a different environment (and we ended up breaking up shortly after returning lol). Over the last ten years, I’ve had a few trips with a guy I dated. Some we ended up breaking up right after returning, while others were great, but we separated over other challenges. I’m not a relationship expert by any means. What’s here is based on my experience with dating and traveling together, and I hope you’ll find what I’ve learned helpful.

Plan together

For those of us who travel regularly and are often the go-to source for our family and friends, it’s easy to want to take charge and put together a travel plan for the two of you, but I would encourage you to slow down. Allow your partner the opportunity to engage in the process and let him or her determine their level of comfort with planning. Plus, the planning process is a great opportunity to learn about each other: does he/she like museums, only likes beach vacations, can’t swim, scared to fly on an airplane, etc.

Additionally, this is a great time to designate responsibility and build trust that he or she holds up their end. For example, you might be in charge of tickets to a show, while he arranges airport transportation. If you get to your destination and one of you haven't done your part, and then it’s met with hostility (you were supposed to remind me!) instead of ownership (My bad, I will take care of it now) pay attention. The guy I went to Montreal with never fulfilled his part of the trip arrangements. And that’s how he was during our year together - unreliable.

Talk about travel styles

I’m a budget traveler, but I’m not staying in anyone’s hostel. I also can’t afford The Peninsula Hotel. So I’m usually booking someone’s home on Airbnb. When you travel together, you’re almost forced to talk about travel styles. Are you into fine dining every day, five-star hotels, hostels, Airbnb, street food, etc? Be open and honest so you can learn more about each other and yourselves. What are your own limits and where do you draw the line? There’s something sexy in compromise/finding common ground, too. It feels really good when you’re going back and forth and ultimately settle on a trip with a style that suits you both.

I dated a dude who was well-off. We discussed going on a trip and when he was sending me his hotel/lodging suggestions, I balked. Even splitting the bill (which was his intent) wasn’t possible. While we knew we lived different lives financially (he owned his home in Chelsea, Manhattan, and I was renting with a roommate in Crown Heights, Brooklyn), this was our first time having to deal with it so directly. When I presented alternative options, he let it go and suggested we look into it when I get a better job. Through planning a trip together, he learned his limits and I was grateful this all happened fairly early on.

Attitude/Energy in dynamic situations

There’s usually some snafus along the way. Flight delay/cancellation, the hotel only has double beds, Airbnb not up to standards, etc. Pay attention to how you treat one another, and any staff, during these situations. This isn’t to say you go looking for signs of trouble, but don’t ignore things like waving you away with his hand when resolving an issue or if she’s rude to airport staff over a flight delay.

Each other’s space

Sharing a home with someone can be challenging, so a hotel room or Airbnb is a great opportunity to glimpse how each other lives. I’m the guy who walks in and immediately sheds everything. There’s a trail of clothes leading straight to the toilet. I don’t unpack a single thing from my suitcase either. Instead, I find a little corner and just live out of it. I love this part of traveling together because it forces you to think about what it would be like on a daily basis. If I notice the person I’m with is super neat, I use the opportunity to talk and make us create an environment where we're both comfortable. I had a guy just take over my suitcase and arrange everything. It was a huge turn on, but I asked...you gonna do that rest of our lives?

Again, I’m not a relationship expert (I’m very much single), but something about travel reveals who we are. We’re presented with challenges and conversations that we're forced to navigate together and if we’re paying attention our actions speak loud and clear. Like Dr. Maya Angelou said, “when someone shows you who they are, believe them.” So go ahead and book that trip together so you can reveal yourselves to each other.

And let us know of your own experiences with dating and travel! Any suggestions?