Interview: Moshe Kasher & Natasha Leggero turn couples counseling into one raunchy roast

Comedians Moshe Kasher and Natasha Leggero have given plenty of advice to a lot of random couples over the span of their “Endless Honeymoon Tour,” but one tidbit, to a concerned male, stands out from the rest: “Man up and take the finger.”

Because every comic is qualified to give tips on anal in the bedroom.

Since tying the knot in late 2015, Kasher and Leggero have toured the country on their post-nuptial standup tour, where the couple gives sporadic guidance on the art of looooove to willing and thoroughly quirky couples in the audience. While they give fairly veritable advice, most sessions turn into a mini-roast by the end (which pretty much everyone is okay with).

The “Honeymoon Tour” rolls up to The Wilbur this Saturday (July 29), marking Leggero’s first gig in the theater, and a return appearance for Kasher. “I love that theater so much,” Kasher says, “it’s such a great place to see comedy, and Boston crowds are so fun.”

We caught up with the couple prior to their show this weekend and talked about the origins of the tour, what it’s like to be on the road with your significant other, and some of the more morbid details of their actual honeymoon. If the lede didn’t suggest this might be a raunchy conversation, consider yourselves now warned.

Victoria Wasylak: I was watching some clips of you guys doing your show together before, and if someone comes to you with a serious problem — for example, one couple was disagreeing on whether or not they wanted to get married — how do you take something like that and make it funny?

Moshe Kasher: [laughs] That’s a good question. There was one situation at one show — I don’t think we kept it in [the video] — but the guy goes, “Yeah, I think a lot of my problems stem from the fact that no member of my family touched me physically at any point in my childhood.” And we were like “okay… well that’s about all the time we’ve got here” and there were tumbleweeds rolling through the comedy club.

Natasha Leggero: But usually we make it funny. Moshe, you’re kind of a master at that.

Moshe: Yeah, I mean, honestly the truth is, it doesn’t scare me when a situation gets dark like that because there’s actually more opportunity for funny there. It’s kind of like “Why are you bringing this up in this public forum?” There’s a place right between where a crowd decides they hate you and they love you, and it’s the perfect place for a great show.

I’d like to think that if someone had deep-seated issues with their spouse they wouldn’t get up there and tell everybody about it, but —

Natasha: You’d be surprised. A lot of the time, the people aren’t used to being very open, so this is an opportunity to confront the things they’ve been thinking of.

Moshe: It’s kind of like when you have a podcast — I’m not sure how many of your readers have had the opportunity to be on a podcast, but so many people have podcasts that eventually, I heard by 2020, every citizen in America will have their own podcast, so everyone in America will have the opportunity to be on one. But often you go into these comedy shows/podcasts, and you sit down and think you’re going to be diplomatic, and an hour goes by, and you’re like “Wait, why did I just reveal that I was locked in a closet for 17 years of my life? My deep dark secret just came out.”

Do you ever think that the people who come onstage and tell you their problems are making it up?

Natasha: Well sometimes I think people have ridiculous problems. This guy brought up his girlfriend and he was like “I hate the way she drinks [from] her water bottle, she squeezes it after.”

Moshe: It’s the crinkle shit.

Natasha: And she demonstrated for us and she was like “This is normal” — and it was NOT normal. Obviously when you live with someone, there’s little things that you start to recognize, and they can slowly drive you crazy if you don’t address it. I like the kind of problems that are fixable. You can stop crinkling a water bottle and throwing it across the room when you’re done with it. There are other things that are harder to stop, like you’re allergic to dogs, or whatever it is.

Moshe: The other cool thing about the show is that you pay to see a stand-up show, and what you get is two stand-up shows and a live relationship counseling session that’ll be funny as any part of the stand-up show. It’s kind of three shows for the price of one. [Corny salesman voice] I’m thinking in terms of how to get you the best deal you can.

What is the craziest thing that someone has come onstage and said about their relationship thus far?

Moshe: At the Tucson show, the guy came up onstage and he’s basically like — he was talking about his wife [as if she] was obsessed with bending him over and fucking him with a strap-on. And we were like “That is pretty intense, it’s pretty intense that you want to do that, and weird that you’re that offended that he isn’t into that.” And basically, as we talk to him for 15 minutes we revealed that she just wanted to kinda tickle it with her finger one time, and he’s still freaked out by it. We were like, “This is a non-issue.”

Natasha: Well, if it’s that big of an issue to him for her to touch his asshole with her pinky, and she wants it so bad, I don’t think that relationship really has a life.

Moshe: As I told the guy, he just needed to man up and take the finger.

I mean, when you’re going to be in a relationship with someone for a long time, that’s gonna happen eventually. It’s inevitable, whether it’s on purpose or accidental.

Moshe: I don’t know how it would accidentally happen. I think this reveals more about the lovers you’ve had who are pretending these things are accidental.

Natasha: Or her.

Oh my god, this has been turned around against me! I… uh… I have to stop talking about myself… Where did this idea come from for you guys to do this to begin with? This is a pretty novel thing — I would assume if most people are doing this, they’re “actual therapists,” not comedians.

Moshe: I think we basically realized that if people come to see a couple, they want to see a couple, they don’t just want to see two people separately, they want us together. So were trying to think of how we could do it, and we realized we had been married almost eight months, so we were totally relationship experts.

Were you ever afraid of burning out from being with each other — like getting sick of each other from being together constantly on this tour?

Natasha: We’re together all the time anyways.

Moshe: Yeah, we’re kind of sick of each other already anyways, you know?

Natasha: When you decide to get married, usually the person you decide to marry is the person who hopefully doesn’t annoy you at all.

Moshe: That’s true. Those were in my vows: “I want to say to you that you’re the person who annoys me the least.”

Were you able to have an actual honeymoon?

Moshe: We did, we went to Bora Bora. We were on a shuttle with a bunch of other honeymooning couples, and there’s nothing that makes you feel less romantic that going to a honeymoon destination because everybody there will have gotten married on the literal same day as you.

Natasha: We found out everyone on this shuttle had gotten married October 11, the same date as us.

That doesn’t even make you feel special!

Moshe: Exactly — and we were driving along and a dog runs out into the street and the driver straight-up runs it over. Doesn’t stop, doesn’t look back, doesn’t even look like he’s affected by it. Righ ‘tash?

Natasha: Oh, it was crazy. And we were on our way to a restaurant, and all of us were just silent for the rest of the trip, and when we got out, I was like “I’m going to say something to him.” And I said to the guy, “You know, you killed that dog back there.”

Moshe: No, no, no, that’s not how it went! You said, “You ran that dog over and you just kept going,” and the guy starts laughing. And he goes, “haha, yes” — what did he say ‘tash?

Natasha: “Dog dead.”

Moshe: “Dog dead. Too many dog.” That’s what he said.

You know, that’s exactly the kind of memory you want from your honeymoon, right?

Moshe: Yeah, we made love like passionate dogs that night. Although Natasha nor I have decided who it was that said something to the driver, so that still has to be discovered.

Natasha: It was me!

Moshe: Okay ‘tash, whatever you say.

Do you ever get sick of people asking questions about your relationship?

Moshe: No. Our relationship is endlessly interesting, both to us and America.

Has there ever been a piece of advice that you gave that backfired?

Moshe: I don’t know, but we did get a couple married, right ‘tash?

Natasha: Yes, that was good. They were on the verge of breaking up, and they weren’t sure what was happening, and after our relationship counseling, they have since tweeted at us that they’re married and happy.

Moshe: So if you’re on the fence with your lover, come to the show and we’ll either get you married or broken up.

There’s this joke that whenever you give advice, you have to say “idk tho” at the end of it so that if the advice backfires and ruins the person’s life, it’s not your fault.

Moshe: We’re actually experts so, wdk, which is we do know.

MOSHE KASHER & NATASHA LEGGERO: THE ENDLESS HONEYMOON TOUR :: Saturday, July 29 at The Wilbur, 246 Tremont St. in Boston, MA :: 7 p.m., all ages, $29 :: Advance tickets :: Wilbur event page :: Featured photo by Robin Von Swank