Booking A Trip While Dating: The Pros, The Cons, And Face Palms

This post was contributed by Steven Knollmeyer. 

There’s a line from the cinematic masterpiece, Mamma Mia 2: Here We Go Again, right before the big “Why Did It Have to Be Me?” musical number with the blonde guy [that has the most geographically unidentifiable fake accent, but he’s hot with a sailboat off the coast of Italy so do we really care?] that goes: “[you’re] the guy that genuinely falls in love every evening, only to fall out of it the next morning.”

Boy, can I tell you that when I first heard this line while sitting alone in a Dallas, Texas movie theater after my flight got delayed during a layover and I decided to make a day trip out of it (another story) I. Felt. ATTACKED. I’d be lying if I said I don’t fall in and out of love quicker than flight prices are dropping from the media over-sensationalizing the coronavirus. This is the story of when I booked a non-refundable international trip with a stranger I met on Tinder on only our second Tinder date and knowing each other for 5 hours collectively.

Date 1: Match with a Belgian cutie studying abroad here in New York on Tinder. We grab drinks at my favorite speakeasy in the city (anyone visiting New York, I highly recommend Attaboy on Elridge Street.) After drink number two, I texted my roommates that I’m marrying him. He mentions that he wants to stop in Iceland before he goes home after the semester- I, jokingly but not jokingly, tell him I would join him. We shake hands, “deal.”

Date 2: Drinks at another speakeasy I Googled beforehand trying to seem real cool. Iceland comes up again. “F*ck it, let’s book it.” “Booked.”

This trip was 4 months away – no insurance, no way out. Luckily we still dated for a few months after that… until about a month prior to the trip. I’ll spare you the dramatic breakup story but here’s a rough breakdown: Belgian Boy™ fell in love with another foreign exchange student from Europe, I chugged a Four Loko at 11am after getting the news via text, by the ultimate graces of the universe I somehow ran into my celebrity crush that evening at a bar where he got me as drunk as humanly possible with him until 4am while picking up my tab (note to self to write that story down), and almost missed my 6am flight home for Christmas the next morning because ya boy was a mess.

Jump to the day of the trip: I see Belgian Boy™ for the first time as I’m sitting at our Icelandair gate in Terminal 7 of JFK Airport. We’ve gone a month without seeing each other with our only communication being fighting via text. So now we get into:

The cons of booking a trip with someone you’re dating:

  • As in love as you feel in the moment you book your trip, there’s a chance things will happen and your feelings towards the person will change

  • If you’re stupid like me and don’t get travel insurance, you have the potential to be out a lot of money if things with you two [or more, I don’t know your relationship!] go south

  • If you do break up and also have the aforementioned Four Loko like me, there is chance that you may [hypothetically, of course] message your Airbnb host in a rage telling them that you have no idea who the person you were dating is and claim they stole your credit card to book this in efforts to try to get out of this trip, therefore potentially hurting your Airbnb rating for future trips.

  • You will learn a lot more about a person while traveling, and you may not like some things you discover about them.

Now, switching gears to the pros of booking a trip with someone you’re dating:

  • My first bullet is the same as my last con – you will learn a lot more about a person while traveling. While you may find annoying traits about how they are as a traveler (if they clap when the plane lands, gurl run, I don’t care how perfect they are), you may also discover a lot of new traits you haven’t seen before that you like. As we know, traveling brings out attributes of us that we may not know we have or express while comfortable at home, so this can be an opportunity to know your person on a deeper level.

  • You’re forced to figure things out. Did I mention that the Airbnb Belgian Boy™and I booked was in the middle of the mountains with no WiFi or cell service and we had to share the only bed in the cabin? Yeah. You’re forced to have conversations and talk things out. If you’re like me, while you may not have found the love of your life at least you’re forced to find closure so you can move on.

  • You’re traveling. Duh, I know, but whether you and the person you’re dating are in a good or bad place when you arrive, you have the chance to engulf yourself in a new culture and only you can allow yourself to immerse yourself in it whether the person joins you or not. And if they do, jackpot, you’ve found yourself a good one.

So is booking a trip with someone you’re dating a good idea? Listen to your gut. Even while my gut was filled with lust and fantasy, and things didn’t go as planned, I don’t regret my Iceland trip in the slightest. I learned, got the closure I wouldn’t have if I didn’t go, and, most importantly, I got to pet numerous wild Icelandic ponies.


Meet Steven: Another twenty-something New Yorker that can be found anywhere tacos and bottomless mimosas are served. Keep up with him on IG. 

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