Unfaithfulness is funny in Cheat: A Man's Guide to Infidelity

A Q & A with comedian Joe DeRosa on his field guide to philandering

Other than perhaps being a rock star or an airline pilot, is traveling the world as a stand-up comedian the best profession for a serial cheater?


Let me start by emphasizing that we are not serial cheaters. Although it is a lifestyle we once partook in, we don’t partake in it anymore ... We are not telling you that you should cheat. We are just telling you how to. A lot of people are going to cheat regardless, but they do not always do it the proper way. As a result, they end up hurting people — themselves and others ...

As comedians, was the main point of this book to entertain or inform?


The main goal was to entertain. It's a social commentary. It will let men learn a bit about themselves and it will let women learn a little bit more about men, but the main goal was to be funny.


What do you think the prevalence of cheating says about human nature or monogamy as the relationship standard in western culture? Is monogamy natural for humans?


I don't think it is natural or unnatural. I think it is a thing that humans are capable of doing, and a thing many people are incapable of doing because of their animalistic traits. Humans are a tricky species. There is an animal base with a progressive coating. On the one hand I understand if someone says, "I will rise to the challenge of monogamy" — because it is a challenge no matter how you slice it. I think that is great and we all applaud that. At the same time, if you are someone who can't quite swallow the pill of monogamy, we are certainly willing to recognize that there are genetic and biological reasons for that, and that is okay too. At that point, when you decide you're going to be someone who chooses a lifestyle that doesn't respect monogamy, for lack of a better term, you must also decide if you are going to be someone who lives a lifestyle with some sort of ethical morality to it, or if you are just going to be completely selfish. It's never good to be completely selfish.


Joe DeRosa
  • Brian Friedman
  • Joe DeRosa
The book touches on the idea that, as opposed to men, women have evolved to use their minds more than their physical might in order to get what they want. Because of this, do you think women are better equipped to get away with cheating?


I certainly think women are better at lying. Men have a very dismissive attitude. When a man lies he says things like, "What are you talking about? You're nuts." ... When women are caught lying, they have this technique of making you feel guilty for questioning them. You start thinking, "Why am I questioning her about sleeping with my friend. She is a nice girl. She probably didn't do that. Wait a minute. Yes she did."


In this book, and usually any time men write about being cheaters, the writer gives an anecdote of the first time he had his heart broken by an unfaithful partner. Do you think this is just a flimsy justification for cheating, or do you think cheaters are born from faithful partners who get their hearts broken by other cheaters?


I don't think a guy has to have his heart broken to become a cheater, but I do think that is the motivation for many guys. Pain is one of the primary reasons that motivates us to act on our own behalf. So, yeah, I think that is a huge reason, but I don't think it is a necessary reason.


When a guy has sex for the first time, it is often like a watershed; pretty soon all he wants to do is have sex. Does cheating have the same impact on a man's psyche? After you cheat once, you break the seal, and you want to do it more?


It depends on the person you are and your lifestyle. Some people cheat and think, "Oh my God, that was a huge mistake. I should never ever do that again." And they don't. Some people cheat and think, "Oh my God, this is what I want. I want to have multiple partners. I don't want to be married or in a relationship." Other people cheat and think, "Wow, I am worth something. This other wonderful person made me feel value again, whereas the person I am with at home is abusive, demanding, and soul sucking."


There are all types of situation you can be in that might provoke you to cheat, and there are all types of reactions you can have. This book discusses the nature of cheating and why people have the impulse to cheat. Many people don't understand why they want to cheat, or if they really do want to do it, so they end up making mistakes because they act on impulse without thinking it through. That is very potentially damaging behavior. The book explores this.


Groups of women on vacation in places like Vegas seem like fertile ground for finding people to cheat with. The problem with these groups is trying to get one to break away from the pack and spend time with you alone. Like you, she may be in a relationship back home and not want her friends to know what she is doing. Do you have any strategies for extracting these women from their friends?


That is more of a "trying to get laid" question than a cheating strategy question. I would just say, you better charm the fucking pants off of her so you can get her to the point where she is like "fuck you" to her friends. That is a huge wall you have to climb over. But, sometimes the friends are great wing-people. I've learned that if a girl is with her real friends, and you are not coming off as a creep, her friends will usually say go. They want their friend to have fun and get laid. If a girl is with girls who are not her true friends, and they are selfish people, those are the ones who will try to say "no, she is staying with us," because they want her to be miserable with them. I've also found that when a woman cock-blocks you she is not always trying to ruin your night. Sometimes what she is trying to say is, "This is an ungodly whore who fucks everything that moves."


The book presents the two main strategies of either lying to a woman you want to cheat with, or of being honest about your relationship. If you choose to be honest, is it better to charm a woman first, to get her on the hook, before dropping the news that you are taken. Or, do you think you should be upfront with this information from the beginning so you don't waste time, so she drops her defenses as she assumes you will not try to sleep with her, or to potentially raise your value as someone for whose attention she must compete?


There are different approaches, which we talk about in the book. There is the brutal honesty approach. You say, "Look, this is my situation. Take it or leave it." Then it becomes a numbers game of who will go for that. Then there is the approach of giving a half truth, of saying, "I do have a girl, but here is the deal with us, and it is kind of ending," even though it is not. Then there is the approach of just not telling her anything. The book explains how the more you lie, the more complicated your life will be. If you are going to lie, you have to understand how to keep those plates spinning, because it is a lot of spinning plates.


For many woman, feeling special, like she is the only one who can make you feel a certain way, is a huge part of what turns them on. How do you make a potential cheat feel special while simultaneously being honest about the fact that you are in a good relationship, or is this illusion even necessary? I suppose some women don't need to feel special to be aroused or they get off on the thought of doing something naughty.


...Your approach determines what kind of woman you meet, and how the situation will end. If you tell a woman, "Hey, I’m in a relationship. I just want to have a fling on the side with no strings attached." The women who go for that are not the women who need flowers or to be twirled around the dance floor. If she accepts your circumstances, she will probably not be that demanding from you in the emotional dependency department. Whereas, if say you are single, and you start dating someone, well, that's a much more potentially dangerous situation, because then things are more likely to blow up.


Would it have been more difficult to sell this book to Simon & Schuster if it had not been written by comedians? If a guy came out with a cheating manual that was more serious as opposed to entertaining, would men be less likely to buy it for fear of angering their current partner?


If the author's message was, "Hey man, go cheat. Go get your dick dirty," I think anyone would react poorly to that, whether it was meant to be funny or not. The key to this book is, yes, it is meant to be funny and entertaining. And again, we come out of the gate saying, look, we're like bank robbers who got caught, and we are going to tell you how we did it ...


Check out more at CheatAMansGuide.com and JoeDeRosaComedy.com.


Follow Shawn Alff on Twitter or Facebook and email him here

A quick wit is as powerful a tool of seduction as a beefed-up bank account. While they don't always look it, comedians who kill on stage often kill on the pickup scene. Not only do they have the confidence to make fools of themselves when approaching random women, they have enough comedic material to keep women laughing all the way to the bedroom. The unassuming Lotharios and reformed cheaters, Bill Burr, Joe DeRosa and Robert Kelly unveil their strategies and stories of living as monogamy outlaws in Cheat: A Man's Guide to Infidelity. I caught up with DeRosa to pick his brain on the finer points of how to successfully cheat.

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