How to Travel With Your Partner, From Two Comedians Who Tour Together

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Natasha Leggero and Moshe Kasher. Photo: Jesse Grant/Getty Images for Comedy Central

Theoretically, the romantic summer getaway means lazy days spent alongside bodies of water, drinking mai tais and indulging carnal appetites with the vigor of juvenile rabbits. Practically, such a holiday means labyrinthine airport-security lines, claustrophobic car rides, and arguments about whether Yelpers in rural Arkansas would know good carne asada if it bit them on the ass. In an attempt to ease a few of the more challenging, painfully pedestrian aspects of vacationing with a partner, we’ve collected tips from two comedians who not only travel for a living, but often do so as a unit. Natasha Leggero, the co-creator of Comedy Central’s Another Period, and Moshe Kasher, the author of Kasher in the Rye and star of the hour-long Live in Oakland special, have been traveling and touring as a duo since early in their dating life. Kasher and Leggero married in 2015, and have been doing shows as part of their Endless Honeymoon Tour ever since. They will be stopping in Brooklyn, Philadelphia, Chicago, and Minneapolis on dates through August 9. For tickets and more information go to natashaleggero.com or moshekasher.com.

Tip: Test new relationships with a vacation
Natasha Leggero: Traveling is a good catalyst. If you’re wondering whether or not this relationship is the one, go on a vacation together. I dated this guy once in college. We were in the car, and every single establishment we passed, he said the name out loud and pointed at it. I was like, I can’t be with this person for another day.

Moshe Kasher: It’s almost a cliché, but it is a good acid test. And by acid test, I mean, the first time Natasha and I went on vacation together I dosed her drink with, like, 30 hits of acid. And I convinced her that I was her creator, godhead figure, and king. She’s been here ever since.

Leggero: There are other deal breakers. I’ve broken up with two guys because they wanted to go to Disneyland. And I was like, I will never enjoy this.

Kasher: One of the charitable things Natasha did, in the early days of our relationship, was tell me that story four or five times so I would know better than to ever suggest a trip to Disneyland.

Leggero: I remember improv classes I took in L.A., you had to shut your eyes and imagine the most beautiful place on earth. You wouldn’t believe how many men imagined Disneyland. And that’s just sad.

Tip: Address the big disagreements early
Leggero: Moshe and I first started traveling, we ran into some real issues because Moshe thinks hotels should be less than $100.

Kasher: I think hotels should have an extra s in the word, and that you should be sleeping on bunk beds with European strangers. Natasha thinks everything should be gilded leather and crushed velvet where a serving person is fanning you with peacock feathers as you walk in the door.

Leggero: When we first started dating, we went to this hotel in New Orleans and I just decided to tell him it was a different rate than what it was.

Kasher: She’s having a hard time finding the words because interviews are sometimes high pressure. She lied to me about how much the room was.

Leggero: It was a nicer hotel, so of course they slipped the bill underneath the door with Moshe’s name on it, and he opened it. And we got into a huge fight about that.

Kasher: I got a little street. I was like, “You don’t lie to me about my money.”

Leggero: Then we came up with this amazing plan: He paid for all our meals, and I paid for all of our hotels. And he never again asked me how much it cost.

Tip: After conflict, find compromise
Leggero: As a comedian, you’re on the road so much. If you’re not staying in a place that’s at least as nice as your house, it can get kind of lonely and depressing. Nice hotels make it more fun for me. And guess what? Moshe’s sitting next to me, right here, right now, in a nice bathrobe with matching slippers from the hotel.

Kasher: But I’m also wearing a patch on my robe from my union. As the International Brotherhood of Steelworkers knows, I’m still with you fellas.

Leggero: I do think that was an important compromise.

Kasher: Much like the rest of the country’s political dynamic, people have to figure out solutions in dealing with things that diametrically oppose them.

Tip: Explore the surroundings, but stay comfortable
Leggero: One thing that inspires me is a quote I read a long time ago, and Moshe always makes fun of me when I repeat it, but it’s basically that a tourist comes to see what he planned to see and a traveler sees what they see. There’s something nice about exploring and tumbling around and seeing what happens.

Kasher: Yeah, Natasha is a huge Blues Traveler fan. In terms of being a comedian, it can be a hindrance to travel with somebody. Traveling alone creates this desperate discomfort, sore-thumb loneliness that creates stories. You can find stories in them.

Leggero: You can still find stories when you’re with someone, you just have to fight about who gets them.

Kasher: The truth is, when you’re on the road as a comic, a third of the time you’re in a cool city and two-thirds of the time you’re in the middle of nowhere in a hotel in a shopping-mall parking lot. The club is in the mall and the show is the only time that is interesting. The difference between having a good weekend and having a bad weekend is having one friend in that city. So both Natasha and I spent years and years traveling like that, where you’re in a Courtyard Marriott in the middle of nowhere.

Leggero: For five days. And you’ll be at these intersections among freeways where you can see a Starbucks but you can’t quite figure out how to get to it.

Kasher: You have to jaywalk across a four-lane highway. There is something very cool about having taken the loneliness of the road. It’s definitely worth missing out on a few stories to figure out how to hang out and create a few of our own.

Leggero: I do feel bad though, because there used to be a lot of cocktail waitresses he could have sex with and it’s harder now to do that.

Kasher: It’s definitely harder, but not impossible. Natasha goes onstage for a cool 30 minutes, so you never know what’s happening.

Tip: When in doubt, distract
Kasher: Podcasting has changed the “get the fuck away from me” moment in our lives. Throw one on and suddenly you’re listening to Ira Glass’s whimsical observations about the human condition. You don’t need space anymore because Ira’s giving it to you. The truth is, Natasha and I don’t fight very often. And we don’t get sick of one another very often. And I think when I figured that part out, I was like, Okay, I think I can marry this girl.

ML: That’s an important quality when you’re looking for a partner: They can’t annoy the shit out of you.

Kasher: It’s funny for how many couples that is just not true. I’m a hopeless romantic, so like I said, I looked in her eyes one day and I realized, this gal barely annoyed me at all. And so I knew we could make a life together.

Tip: Find common wants
Kasher: The thing about being single is you have this notion that freedom is only dependent on being alone and being an individual. Same thing is true of being a traveler. The most annoying thing about traveling with other people is trying to align your desire on this trip with their desires. You have to figure out a way to let your desires harmonize. And also, on a comedy tour, you have to figure out which person in the couple kills. That can really affect the next day.

Leggero: Right, if I’ve had a really bad set and Moshe destroys, probably we won’t have a great next 24 hours.

Kasher: And if I’ve had a really bad set and she destroys — actually, I can’t really picture what that’s like.

Tip: Keep busy during down time
Leggero: Moshe’s much better at that than I am, because he has this little traveling video-game contraption. What’s it called?

Kasher: It’s called a Nintendo Switch and it’s only for really cool dudes.

Leggero: So Moshe pulls that out and I’ll continue to ask him a million questions while he’s doing it. I think because he feels slightly guilty that he’s playing with a toy that a child plays with, he will indulge me sometimes.

Kasher: Based on your tone, I’m going to sic my homies in the Gamergate community on you, my wife. I remember when in Turkey, flying back to the states, and thanks to the new administration, you can’t have a laptop or any electronic devices on any incoming flights from Muslim countries. It’s kind of a cool vibe.

Leggero: Especially that two-hour wait in line before and after you fly to take away and give back your electronic devices.

Kasher: But for some reason, they let you keep your phone. So I was trying to negotiate with this Turkish customs guy to let me keep my Nintendo Switch and he can keep the phone. And I was like, “They’re basically the same size.” And the guy just turned to me and spoke in English, “Look, man, I like video games, too, but I cannot do it.” He wanted me to know that he empathized, but that he, too, felt hopeless in what is a crushing tidal current of the current realpolitik. Just as I am a cog in the great political waterwheel, he too is a cog in the great political waterwheel. And that we wished there was a way we could both not play Zelda.

Leggero: And then I informed both of them that “Switch” is pronounced “adult baby toy.”

Kasher: In Turkish.

Leggero: Moshe was forced to make conversation with me that entire trip and we had a beautiful time.

Tip: Learn something from every place you visit
Kasher and Leggero kept a diary about every show on this year’s Endless Honeymoon Tour, and the following are things they learned in each city.

New Orleans: Never have your father get in touch with distant family members in rural Louisiana through ancestry.com, and have them sit in the front row at a show.

Atlanta: During the segment of the show in which we do relationship counseling, a webcam model (who fucked herself for straight guys’ credit-card numbers) came on and said her problem was that her boyfriend was too controlling. We informed her that he is not controlling: She is a sex worker and he is cool with it.

Miami: The hotel had a bottle of rosé for us, and we brought it to give to the best couple in our counseling segment. We picked a couple where the problem wasn’t stated out loud, but let’s just say the male member of this 18-year-old couple did essentially rhythm gymnastics getting to the stage, and talked about how he loved Adele. The girl said his problem was that he was too dramatic. So you fill it in. We gave them the rosé, it felt appropriate.

Boston: We had an amazing show, but it seemed like everyone in the city woke up, put on a blindfold, and then reached into a pile of dirty exercise clothes to get dressed.

How to Travel With Your Partner, From Two Married Comedians