Sex Advice From

Sex Advice from Comedian Ari Shaffir

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Ari Shaffir, the man behind The Amazing Racist, is having a good year. He’s got a new stand-up special, “Paid Regular” coming out 1/16 and a second season of his hilarious storytelling series, “This is Not Happening” out 1/22. Both are premiering on Comedy Central. Nerve caught up with Ari to chat about comedy groupies, doing mushrooms, and how sexting has evolved.

You didn’t lose your virginity until college. Are you making up for lost time?
It’s possible. Comedian Jeff Dye fucks more women than anyone I know and he was religious or something. Kurt Metzger was the same way, he was late, and so was Pete Holmes. Yeah, we’re all playing catch up.

Are there any benefits to being a late bloomer?
Well, you’re not a kid anymore. You’re 21. I don’t know if that’s a good thing. I’d like to say it’s better to do it that way, but I don’t know if it is. I saw this marathon once, the end of a marathon where 2 guys were neck and neck. They were running down the street and then one of them just veers off to the right. He takes off and he runs about 50ft, and then he looks around. He’s like, “Wait, why’s that guy not…” and then he realizes, “Oh fuck, I’m in the wrong lane.” We’re talking like the last 5 minutes of this marathon, and he went the wrong way. So he starts sprinting to catch up with this guy, and he ended up passing the other guy because he started sprinting. We’re all just sprinting to catch up, really.

Who’s going to be on season two of “This is Not Happening?”
Marc Maron, Joe Rogan, Steve Rannazzisi, Paul Scheer. Rob Corddry, D.L. Hughley. Just a bunch of good people.

“This is Not Happening” was a digital series last year and this season it’s going to be on television.  Were there any differences production-wise going from web series to TV?
There’s very little difference from last year. It’s almost the exact same. Time is the only issue because you have to break for commercials.

This is what I figured out: boys want naked pictures from girls. Girls do not want naked pictures from boys.

Are you on a speakerphone? It’s hard to hear you.
No, I’m on a shitty flip phone. I lost my phone in a cab. I was gonna get another iPhone, but I’m done for a little while. I spend two hours every morning in bed looking at my fucking apps. But it sucks because there’s no Snapchat on this thing, no more naked pictures, no more sexting. Do you know how hard it is to write out a sext using the same button 4 times just to get one letter? It really makes you creative.

On some phones you can talk into it and it will write the text for you. Do you ever command Siri to sext for you? Is that possible?
No I never did that [laughs]. I’m an English major, so I was always like, “I can write this.” This is what I figured out: boys want naked pictures from girls. Girls do not want naked pictures from boys. Occasionally a girl will but really, they don’t. They want stories from guys. They want words. They want us to write down what kind of stuff we’re gonna do to them, and give them visual things that way. So as an English major, I’m way ahead of the curve. If I can write all this stuff, I can have an imagination about it.

Do you think people have gotten more creative with their dick pics? The selfie stick exists now, so the possibilities are endless.
Absolutely, the game has been stepped up. I could use one of those.

In recent years, we’ve gone from dirty texts, to naked pictures, to Snapchat. What do you think sexting will be like in 5 years?
There will be videos of masturbation. That’s the main thing that you want now. The problem is, how do you do that with one hand free? You have to do the videos from really far away. It’s almost impossible.  But with the extender cam, you could set a timer and put it somewhere and angle it. The world is our oyster.

An entire masturbation video might be a little too long.
60 seconds. That’s all you need.

You do a yearly mushroom trip. Have you ever had sex on mushrooms?
I don’t think I have. Although jerking off at the end of it is the best.

You’ve said everyone should try mushrooms, but I did them once and had a terrible time.
Every person that does it is either basing it on zero experience or one experience ever. That’s like getting into traffic the first time driving and then saying, “Driving is not for me.” You had one try and it wasn’t great. The people you’re with and the specific frame of mind you’re in is important. If you just got fired or you’re in the middle of a bad break up, that’s probably not going to be the best for you because your mind is going to wander onto those things.

I had a friend tell me he had his first bad trip because he was with a guy he barely knew and a girl he sort of liked but hadn’t done anything with. He was really worried about the way he was acting and stuff. Then it just gets really weird.

Do you think it’s easier to get laid as a comedian or a musician?
It’s gotta be musician, but it has to be a high level musician. Actually, low level works too. I know some low level musicians that do shows sometimes and after the shows, everyone just hangs around. People just follow you around, because you’re a rock star. A comedy show ends, and then everyone goes home.

But sometimes people hang around after comedy shows.
It happens, but I don’t think it’s as easy as when you’re a musician. No one is ever angry at a musician after the show. That doesn’t happen. The type of people that go to rock clubs are fuckers. There’s a way lower percentage of fuckers going to comedy shows.

Are you familiar with the term “chuckle fucker?”
Nobody uses that term anymore. That’s not a real term.  It’s gross. That doesn’t show any creativity. That was the term 15 years ago.

So then what’s the term for someone trying to have sex with comedians?
I don’t know. Groupie…maybe.

Now let’s do some advice questions. “My boyfriend gets off on dirty talking, but I’m bad at it. Are there any good go-to phrases I can use?”
I actually have the same problem. I feel like a fool. I guess you’ve got to confidently talk about something you’ve never really talked about before. You can’t be like, “You want me to do it like…this? You want me to stick it where?” If you try anything confidently, it’s probably gonna work. Try something like, “I love the way your dick fills me up.” I don’t know.

If you try anything confidently, it’s probably gonna work.

“I’m terribly shy around women I find attractive. How do I overcome this fear?”
One way is hookers, just get with a bunch of them until you’re like, “Ugh, who cares anymore?” Attractive women don’t feel attractive. They feel just like you and me. If you treat them like they’re more special, you’ll feel like you have to get their approval. It’s kind of like when I see celebrities around Hollywood and people are like, “Oh we gotta make sure they’re ok.” But really, they’re just like regular people.

Hot women are looking for approval the same way everybody else does. I went to Shanghai this year: a city of 24 million people. There are 50,000 expats there from different countries. There are 25,000 white women, and they’re being ignored by 12 million  men. They don’t know how to handle it. They’re used to being hit on their entire lives, and now they’re being ignored by so many people. It breaks them down and they’re all more willing to have sex.  They just want some attention. So the solution is, move to Shanghai.

“I hate going out to bars. What’s another good place to meet single people?”
Bars suck. I was just with somebody last night and he was like, “Let’s go to the East Village and try to pick up girls.” I mean, where do you pick up girls? What are you talking about? We’re just gonna go and talk to girls? That’s crazy.  It’s hard to pick up girls at bars. I mean, I do it at comedy clubs after I get off stage. The best way to meet girls is in college because you have a bunch of friends and then they have a bunch of friends, and sometimes they overlap. Just talk to somebody in a real casual environment. House parties are great for that.