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What Women Taught Simon Rich

What I Learned From Women: Humorist Simon Rich

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Simon Rich can imagine what it's like to be a condom, and it's not fun.

"I born in factory...I stay in wallet long, long time," he writes in "Unprotected," the first in a series of comically mind-bending shorts from "The Last Girlfriend on Earth and Other Love Stories," released in paperback just in time for the complicated 24 hours we call Valentine's Day.

Related: The 10 Worst Reasons to Turn Down a Second Date

The lonely prophylactic is just one of the characters in Rich's collection of romantic gods and monsters, inspired by his own real-life dating exploits. There's also a caveman with a brutal crush on the only woman in existence, a guy on a blind date with a troll, and a clueless Sherlock Holmes dealing with a cheating girlfriend.

The 29-year-old former "Saturday Night Live" writer may be inspired by unlikely characters, but he's learned a lot about love — losing it, finding it, writing about it — from the women in his life. Here are some of the best lessons he's learned, at times, the hard way.

How hard it is to write about love: "This book is really autobiographical, especially the embarrassing parts. I was trying to write about dating because it was consuming my life, but all the stories I wrote about my own personal experiences turned out incredibly boring, because my life is very boring and my experiences are really generic. It took dozens of naturalistic pieces for me to realize that I should stop writing about love, the way it happens, and start writing about the way it feels. Like when you miraculously get a girl to become interested in you, you are expecting a call from the president and the MacArthur genius grant. When your ex-girlfriend is dating someone new, it sometimes feels like she's dating Adolph Hitler. When you're in love with someone and worried that you'll lose her, it's like she's the last girlfriend on Earth."

How dating got to be so stressful: "For thousands of years in most cultures, dates were arranged for you. Being able to pick a partner voluntarily is a relatively recent phenomenon. In a way it was a lot easier thousands of years ago, when you were told whom you were going to marry, because now if you screw up it's your own fault. The fear of getting it wrong is what makes it so high-stakes. The fear of losing someone you're meant to be with. The fear of never finding someone you're meant to be with. It's hard to imagine a higher-stakes fear than that."

How important it is to find a partner who challenges you: "[I'm] definitely inspired by my fiancée, Kathleen [Hale], who this book is dedicated to. I don't know how I was able to write anything without her. She has both a direct and indirect influence on everything I write. She's a writer herself. She writes young adult novels, and they're fantastic. She's definitely a better writer than I am. So it was helpful to really be able to show her everything, because she's not just sympathetic and supportive, she also gives me ideas to make it better."

How to be a comedy writer: "There were a number of really funny women writers at 'SNL' while I was there including my onetime boss Paula Pell, who is a comedy legend — one of the funniest writers and performers I've ever met. She's an incredibly sweet mentor who taught all of us about writing comedy and writing in general. She was like that dream magic professor you always hope you have: brilliant, inspirational, but always patient and taking the time to help make them better. I also learned a ton from ['Saturday Night Live' writer and collaborator] Marika Sawyer. She's one of the funniest writers I've ever met. I mean she's uncompromisingly hilarious."

How to inspire a kid: "Some of my other biggest female influences were my mom, who introduced me to Roald Dahl and Shel Silverstein and my stepmom, who got me my a lifetime subscription to Mad Magazine, which, by the way, is only three years."

How bad dates can be life-changing: "I'm doing a TV show pilot for FX called 'Man Seeking Woman' and it's based on [the book] 'The Last Girlfriend on Earth.' It's a sitcom about a guy looking for love in the big city but he encounters a lot of high stakes supernatural creatures. He gets set up on a blind date with a troll, he finds out his ex is dating Hitler, and so on. We're going to shoot it probably in March, and then hopefully it'll be decent place and they'll give us the whole series. Jonathan Krissel is directing it, and he's the guy who directed 'Portlandia.' My not-so-secret dream is that it goes to series and I'll get to steal Marika from 'SNL' and take her with me. But that's a long ways a way."

How not to wear a suit: There's a character on '30 Rock' that’s based on me, and I think his name is Simon. [ED. NOTE: It is.] The writers who wrote it are friends of mine and they asked me to go downstairs and audition. And I'm such a bad actor that I didn't even get a callback for a character based on me. But they got the oversized suit right. That is definitely how I dress in my mid 20s, which explains some of the dating problems that I had probably in retrospect."

Here's an excerpt from Simon Rich's book, "The Last Girlfriend on Earth" (Back Bay Books). You should probably buy it for someone you love, yourself included, this Valentine’s Day.

Man Seeking Woman
You:
You are an intelligent woman, with a sweet and caring soul. You're mature and sophisticated, but you know how to let loose and have a good time. Your first name is Chloe.
Me:
I am a thoughtful, intelligent guy with a sense of humor. I like to stay up late talking about the big questions. I have a large, irremovable tattoo of the word 'Chloe' on my chest from a previous relationship.

— Sarah B. Weir

Also on Shine:
5 Proven Ways to Improve Your Relationship
6 Simple Reasons New Relationships Fail to Launch
7 Relationships Tips From the 1950s That Still Apply Today

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