After my divorce, I experienced over 500 first dates, sacrificing myself on the altar of online dating, and enduring several lifetimes of crushing pre-date jitters. I emerged with a lighter wallet, an intact sense of humor, and more knowledge than I’d ever anticipated on the art of dating post-divorce. 500 Dates, my first book, composed of 55 humor essays, features the highlights and lowlights of my dating spree.

My essays explore not just dating, but romance, relationships, breakups, attraction, the nature of love, and how both men and women view the art, science, expectations, and reality of courtship in the 21st century. I intended that my experience also serves as a primer on how to turn courtship into something deeper and longer lasting in the modern era. Despite my own dating mishaps, I’m grateful for having retained a sense of hope, proving that the end of a marriage does not mean the end of romance—or one’s sense of humor, despite my lighter wallet.

Top 20 Excerpts from 500 Dates: Dispatches from the Front Lines of the Online Dating Wars: 

1.   What is more important than direct, personal human connection—especially in the world of dating and romance? That’s what I’d often say to a woman to whom I was attracted at a party. And she’d invariably reply, “I agree, and so does my husband who’s approaching us with my drink right now.”

2.   I still believe that true happiness comes from within. But I realize now that on the journey of romance, thrift and creativity will take you only so far—for the rest of the trip, you’ll need MasterCard.

3.   That’s when the solution occurred to me. And it was one that, strangely enough, I’d never even considered before. It was this: I would ask out someone I knew would be available, knew everything about, was good-looking, healthy, had a wonderful personality, shared all my interests, was romantic and passionate, and was really fun to be with. That’s right, my plan was to ask out the only one I knew who fit those qualifications — I planned to ask myself out on a date.

4.   Most guys consider revealing more about themselves emotionally and communicating on a deeper level nearly as enjoyable as falling face-first onto an ice pick—or spending the rest of eternity listening to Celine Dion music.

5.   Having logged 500 dates, I have consumed what scientists refer to in technical terminology as “a buttload of caffeine.” Consequently, I’ve been unable to fall asleep for the past nine years. I am exhausted.

6.   A typical coffee date is exciting and romantic in the same way that a colonoscopy is soothing and carefree.

7.   One first date, she made out with me for half an hour and the next day e-mailed me that she wasn’t interested in meeting again because she didn’t feel the chemistry was there.

8.  Dear Lord, please don’t let this one be a stalker, a jerk, or have serious psychological issues like the last six. I believe I’ve reached my annual quota for restraining orders.

9.  At least six different times, I’ve had dates with the same type of woman — one who has had a long history of wild, impulsive,  passionate, no-holds-barred sex. She invariably finds something lacking in that lifestyle and decides to make a change. Starting with the very next man she dates. Who is invariably me.

10.   To say there was zero attraction is like saying the Ku Klux Klan has no Affirmative Action program. Every minute of that thirty-minute coffee date was an eternity. And those are thirty eternities I’ll never get back again.

11.   Of course it would be so easy if, when you met your soul mate, he or she had a large neon sign overhead flashing “THIS IS THE ONE!” But so few people are considerate enough to appear in our lives bearing the proper oversized neon identification.

12.   I also worry about “settling.” At what point do you look at the person across the table and say to yourself, OK, I’m done looking. She has enough of what I want. I’ll be with her. And then not have the feeling a few months or years down the line, Gee, her bright red hair, guttural German accent, and collection of antique soup ladles didn’t seem quite so annoying when we first met.

13.   They say that with age comes wisdom. OK, so I’ve personally disproved that theory time and time again.

14.   School teaches us every conceivable subject except how to have a successful romantic relationship. That subject you have to figure out all for yourself. And I’m a slow learner. So I estimate that women will really be impressed with my relationship skills by the time I’m ninety.

15.   “I’m as comfortable in a cocktail dress as I am in jeans.”  Tell me, is this a female trait guys desire? It must be because so many women mention it. I mean, I have a number of single male friends, and I honestly can’t recall the last time any of them said to me, “Y’know, Amy is a wonderful woman, but I just don’t think it’ll work—she’s nowhere near as comfortable in her cocktail dress as she is in jeans.”

16.   This is why romantic songs and movies and Hallmark cards are so popular—among women. They bring women a world of Enrique and Antonio and Romeo, instead of the world of women’s unshaven, unemployed date asleep on the couch, in his underwear, snoring, drool dangling from his lips, a half-eaten bag of Cheetos spilled out onto the floor he’s never vacuumed.

17.   Men use cologne when they start dating. This gives women the mistaken impression that their man naturally smells like an exotic rain forest or tropical island breeze.

18.   Men believe that God wouldn’t have given them the ability to make gross noises with their various body parts if He didn’t want them to do so.

19.   Here are the survey’s 3 Best Opening Lines to Get Republican Women Into Bed:

• You know, in this light, when you smile that certain way, you look like you could be Sarah Palin’s younger, more desirable sister.
• To see you naked, I would turn in my own mother to the Department of Homeland Security.
• The tattoo on my penis spells “RAN.” But when I get excited, it spells “REPUBLICAN.”

20.   Spain is claiming that the world’s most passionate and popular kiss—the open-mouthed French kiss—originated, not in France, but in Spain in 1605! “And we have documentation to back that up,” states Julio Salazar, president of the Society for the Promotion of Spanish Kissing.

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