Sex Advice From Todd Barry

The chronically underwhelmed comedian on Def Leppard, tattoos, and Suze Orman.

Last night, my girlfriend of five years suggested that we stop using condoms because it "feels better." I agreed, but I'm totally freaked that she might get pregnant. I'm also worried that she secretly wants to get pregnant. What should I do?
Why did you put quotation marks around "feels better?" It actually does feel better. Anyway, to answer your question: if you've been going out with the same woman for five years and don't have at least two kids, then you are a selfish, selfish man. Let's meet back here in a year, so you can show me a picture of your twins.

I've been seeing this guy for a few months now and even though we've fooled around, we haven't had sex yet. Neither of us are virgins, and he's not afraid of sex, but I can tell he's a little anxious. How can I get him to stop being such a prude?
Tell him if he has sex with you, you guys will go get tiramisu afterwards. Everyone likes tiramisu.

I like watching porn during sex, but I've always been slow to introduce it in the bedroom because it might freak my date out. Should I be worrying about this so much, or should I go ahead and pop in a DVD?
I would pop it in, and if she freaks out say, "Oh my God, sorry about that, sweetie. I thought I was putting in a copy of Suze Orman's The Laws of Money, the Lessons of Life." 

My boyfriend loves giving oral sex, but it makes me really self-conscious. Are there ways to chill out, or should I just forget about it all together?
Your question is so "all over the map" I almost believe he’s performing oral sex on you now. If this is the case (and I’d bet anything it is) I’d say you might want to put the laptop down and focus.

I'm dating a woman fifteen years older than I am who happens to be friends with my mom. How do I tell my mom without her freaking out?
See if you can fuck this woman while she's in the middle of a bridge game with your mom. That would be the least heavy-handed way of letting her know what's going on.

I got drunk and cheated on my girlfriend of three years. It was a one-time thing, and I feel like an asshole. Do I tell her?
I called your girlfriend about this. She was really hurt at first, but then I explained that it was a "one-time thing," and you were drunk when it happened. Then she said, "Whew, for a second I was worried I might be going out with an asshole!"

I want to put on a little strip show for my boyfriend's birthday, but I'm nervous that I'll just end up looking ridiculous. What should I do to make sure it goes off without a hitch?
Just make sure the Def Leppard CD doesn't have any scratches on it. The rest should take care of itself.

I'm going out on a date with a girl I think is way out of my league. How can I make sure I keep my cool and not get so nervous I screw it all up?
Make sure to slip in the phrase "I know you're out my league" as much as possible. For example, "I know you're out of my league, but, do you want to split the crab cake appetizer?" 

My boyfriend wants to get a tattoo of my name on his arm. I love him, but I think that's a terrible idea. How do I talk him out of it without seeming like I'm arguing against the future of our relationship? 
Just say to him, "I don't want you to make the same mistake I did," then lift your shirt to reveal "TODD BARRY" tattooed in a large font across your belly. When he inevitably says "I don't remember seeing that tattoo before," you just respond with "Of course you don't. That's because you don't listen!"

What's the best reason to date Todd Barry?
If I take you out for Thai food during the day, you don't have to order off the lunch menu. 

What has being a comedian taught you about dating?
You mean, what hasn't it taught me?! Actually I don't even understand your question, so I'm going to move on.

I'm running out of effective pick-up lines. I need one that'll get the ladies in one shot. Ideas?
Offer to buy her a drink and then say, "I'm not sure what you're doing tonight, but I just got a copy of Suze Orman's The Courage to be Rich, and I haven't removed the shrink wrap."

Keep up with Todd Barry at www.toddbarry.com.