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

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


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Now several years post-divorce, relationship expert and humorist Mark Miller has experienced more than five hundred first dates. In 500 Dates, composed of fifty-five humor essays, Miller features the highlights and lowlights of those dates.

Among the true dating tales and revelations you will find in this book are:

• How Miller and his date learned the limitations of a man being too emotionally expressive. (“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.")

• Miller’s realization that sometimes men have to pay a heavy price for their dates’ previous relationship behavior.("At least six different times, God has matched me up with a woman 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.")

• Miller’s misguided social experiment to separate dating from status by spending less than $20 on the date, purchasing everything at a 99¢ store, and what he learned, as a result, about his date and himself. (“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.")

• Revealed for the first time the inner workings of a man's brain.
("Cerebellum. Responsible for coordinating movement and maintaining balance. Used primarily when a man has had eight beers and is endeavoring to make his way to the bathroom without tripping over the dog and pulling the fish tank over on top of them.")

• How Miller took his date to his ex-wife’s holiday party only to find his date and his ex-wife bonding like high school girlfriends. (“Pam would take Amy aside and present to her a list of all 273 of my failings, most of which, she confides to Amy, won’t become noticeable until month three of Amy’s being with me. Amy is stunned; she’d only been aware of 149 of my failings.”)

But 500 Dates is about much more than dating. Its humor essays also cover romance, relationships, breakups, attraction, the nature of love, and how both men and women view the art, science, expectations, and reality of courtship and turning courtship into something deeper and longer lasting in the twenty-first century. Throughout these essays, a portion of which were previously published in various media, Miller provides a sense of hope about one’s romantic prospects. Readers will find that the end of a marriage, even a long-term one, does not mean the end of romance—or one's sense of humor.

Product Details

ISBN-13: 9781629144665
Publisher: Skyhorse
Publication date: 02/03/2015
Pages: 272
Product dimensions: 5.40(w) x 9.30(h) x 1.00(d)

About the Author

Mark Miller has held positions as a nationally syndicated dating columnist for the Los Angeles Times, a dating blogger for the Huffington Post (along with a wealth of other publications), a TV sit-com staff writer/producer, a stand-up comic in nightclubs and on TV, and a writer for comedians such as Jay Leno, Dana Carvey, Roseanne Barr, and Jim Carrey. He lives in Los Angeles.

Read an Excerpt



Warning: once you finish this section, you'll know me so well, you'll swear we grew up together — and ask me for the money I still owe you. Every essay in Section One deals with a date I experienced, loved, or endured, depending. Part A gathers together some of my early dates, while I still had on my dating training wheels. Part B explores my more experienced dating history, where I felt pretty confident about being a wonderful boyfriend, if I could just get beyond that first coffee date. And in Part C, I'm feeling as though I'm doomed to ride the dating merry- go-round alone for the remainder of my days. But don't cry for me, Argentina — or even New York, Atlanta, or Kalamazoo. Instead, come ride the dating rapids with me. I think you'll find it invigorating.

Part A: I Dip a Novice Toe into the Dating Pool

You Don't Have to Visit China to See Red Flags

Oh, sure, it started promisingly enough. Rhonda and I had each seen the other's photo and profile on a singles website, granted one another profile approval, and were now talking on the phone for the first time. Things were going pleasantly until Rhonda suggested that I choose a place for us to meet. I suggested a coffee house with outdoor tables at The Grove. She reacted unimpressed. I then mentioned a charming little place on Melrose, with a Japanese tea garden in the back. She yawned. Finally, I offered a quaint French café with outdoor porch seating and fabulous homemade desserts. The silence was deafening.

"Problem?" I inquired. "Those places just aren't very romantic," she informed me. Not very romantic? I was stunned. What are we, celebrating our anniversary? Getting together for Valentine's Day? It's our FIRST MEETING, for crying out loud! We don't even know if we have ANY in-person chemistry! I told Rhonda that to me, any "romance" occurs as a function of the chemistry between the two people. And that chemistry happens (or not) whether the people are meeting at the Polo Lounge of the Beverly Hills Hotel, the Ritz in Paris, or at Taco Bell in Pacoima. She mumbled an unconvinced "I guess so," told me she was on her cell phone in the car, about to park in her garage, and would call me back as soon as she got in the house. I never heard back from her.

I briefly envisioned how I might have salvaged this particular relationship. A romantic gondola ride in the Venice canals with me feeding her grapes while comparing the texture of her skin to velvet? But if it turned out there was no chemistry, or very little chemistry, as is often the case, we'd merely be two people in a romantic setting, eager for the date to end. I just didn't get it. What was she thinking?

And then it occurred to me that this whole episode with Rhonda had been a gift to me from Cupid. You see, sometimes Cupid allows weeks, months, even years to go by before your romantic partner reveals his or her dark side. The longer it takes for the revelation, the harder and more painful are its effects on you when it all comes crashing down.

Other times, as with Rhonda, Cupid is kinder and allows the red flags to reveal themselves right from the start. So you're privy to your partner's deepest dysfunctions early on, in the harsh morning light of his or her true self. Any high-maintenance, humorless, judgmental, controlling, quick- tempered, dull, deceitful, insecure aspects of him or her rear their ugly heads. And at that point, you can decide if all of his or her other wonderful qualities make up for this — or if you would be far better off heading for the hills.

What fascinates me about all of this is that these red flags are revealed despite their owners' intentions of putting their best foot forward during those first few all-important, making-a-good-impression encounters. Sometimes, thankfully, their true colors can't help but slip through as merciful little advance relationship warnings ("The Crazies are coming! The Crazies are coming!"), thereby saving you all that time, money, effort, and emotional involvement (and subsequent hurt) for however long you might have become involved with them before the bad stuff surfaced.

Therefore, I thank you, Rhonda. You did me a favor, and I wish you nothing but the best. I sincerely hope you meet that guy who will be able to suggest a first-date locale sufficiently romantic for your deepest needs and desires. All I ask is that once you're seated with him at that charming seaside bistro on the French Riviera, with doves circling gently overhead and a strolling violinist playing "La Vie en Rose," you'll think of me kindly and wish me luck in my attempt to drum up a modicum of romance in some desolate Starbucks in Culver City.

Dating Women I Can't Afford

Speaking of dates on the French Riviera, I encountered some women with such high financial expectations, that we may as well have been from different universes ...

One thing that's unique about dating as an adult, as opposed to dating back in high school or college, is that certain painful economic realities kick in. One in particular has caused problems recently for me — and that is the hard realization that there are certain women who, no matter how much we have in common, no matter how good our chemistry, no matter how right we seem for each other — are simply out of my economic league. In short, I can't afford them. And it's never me who makes that determination — they do.

When looking for a romantic relationship, I generally look for someone with similar values, interests, personality, temperament, sense of humor, background, etc. I generally don't check for a gold card when I'm searching for a soul mate. Yet it has become painfully clear to me that some people do.

Granted, this doesn't apply to all women. I've dated and had relationships with women who earned far more than I do, and it didn't matter to them — just as it never matters to me what a woman's income is. Still, it's a pail of cold water in the face when the cash factor destroys a promising potential relationship, as it did recently for me.

I arrived to meet Sandy at her house. Her big, expensive house. In a lovely, upscale neighborhood. Inside it was like an art museum.

Let me backtrack for a moment now. Normally, I might have been intimidated or had thoughts that a woman living in a house like this would never go for a lowly apartment-dwelling, Honda Accord-driving creature like myself. But I had screened her dating profile, drawing a blank at finding any of the telltale phrases women use to convey a lust for money: "high-maintenance" ... "fine dining" ... "frequent travel to exotic locales" ... "enjoy being spoiled," etc. Sandy's profile seemed down to earth. And our phone and e-mail chemistry was great.

So, back to the house. I momentarily forgot about the surroundings because it soon became obvious that we had incredible, instantaneous chemistry. We were kissing within 20 minutes of my arrival. We held hands and walked arm in arm to get some brunch. And the talk was good, and telling.

Sandy told me about her wealthy ex-husband with whom she had very little romance. She described a succession of men she dated who had lots of money and took her to all kinds of fancy places, even to Europe. I started feeling a little uncomfortable, trying to imagine her reaction down the line when I suggested Santa Barbara as the exotic locale I could afford for a romantic getaway.

I was up-front with her, telling her that I couldn't provide that kind of lifestyle. I live simply. I go to inexpensive ethnic restaurants. I use grocery coupons. Sandy put me at ease. She said that those wealthy guys she dated didn't have a clue about relating to women. Most were overly consumed with their business dealings. She said she'd rather hang out in a small apartment with someone with whom she felt a genuine connection than be in Paris with someone not fully there for her.

As we walked back to her place, I remember thinking that there are certain times in life when everything seems perfect. And walking arm in arm with this beautiful woman who really seemed to "get it" as far as what was important, this was one of those times. The joy of that thought kept me floating on air for a full day — until Sandy called to let me know that, on second thought, our "lifestyle differences" were something she felt would keep us from being truly compatible.

In today's dating universe, the lack of cash can torpedo your chance for romance. But I'm sticking with the Beatles, as they sing in "Can't Buy Me Love." If I can find someone who adores me, that's as good as gold.

And yet, one day, I couldn't help trying a playful little financial dating experiment.

Does Dating Happiness Come From the Heart or the Wallet?

Dating a woman in Los Angeles can be an expensive proposition. But must it be one? Don't all the greatest religious and spiritual masters tell us that true happiness comes from within? Does genuine dating success require that a man spend over a hundred dollars on his date? Is not a man more than a wallet and some testosterone? Do I ask too many questions?

I decided on a dating expense experiment never before attempted (or at least admitted) in the course of human dating history: I decided I was going to have a wonderful first date and spend less than twenty dollars doing so. That's right, less than twenty bucks on a date in Los Angeles. Okay, I know. I can hear women throughout the city exclaiming, "Cheapskate! Loser! No way!" Hey, they poked fun at Columbus, but he showed them. He found a way of impressing women without having to spend a fortune — simply by discovering a continent. Surely my date will admire my thriftiness, my resourcefulness, my imagination, and my creativity. I'll discover a continent of inexpensive fun.

And so, armed with twenty big ones in cold hard cash, I strode confidently and determinedly into the one place where I knew I'd get great value for my money — the 99 Cent Only Store at the corner of Fairfax and Sixth in Los Angeles, the store with not one, but two mottoes: "Shop Us First! The Smart Shoppers Do!" and "Nothing Over 99 Cents Ever!" I felt at home. I looked for the "Cheap Daters Welcome Here!" sign, but apparently it was being repaired.

Flash forward to the date. I arrive at Sarah's place wearing my playful Looney Tunes tie (a $9.99 value!), with a gift for her — an official Olympics Souvenir Program. A collector's item! It originally sold for $12.95, but I got it for, yes, 99 cents. Oh, sure, it was for the 1984 Olympics, but that makes it a 20th anniversary collector's item. Nor did I forget her cat, whom I surprise with a chicken and seafood Whiskas four- pack. Before we get in the car, I take out a big canister of 21 pieces of jumbo colored chalk, and right there on the sidewalk I create a multicolored heart with Sarah + Mark inside. I bet her wealthy boyfriends never did that! So far, so good!

We drive to the beach (free scenery!), where the heat is no problem because I'm thoughtful enough to bring along Pinnacle Drinking Water, six for 99 cents, with sports cap. We sit there munching on Granny Goose's 13 oz. bag of tortilla chips and Sun-Maid six-pack of raisins. I even immortalize our fun with my new 35mm "Famous Name" 99- cent camera containing 99-cent color print film.

By my count, we had only gone through nine of my twenty dollars of purchases, when Sarah said, "Okay, what's going on?" I said, "What do you mean?" all innocent-like. She mentions my tie, the chalk, the cat food, and goes in my bag and pulls out the remaining purchases, including Sesame Street Chocolate Chip Cookies, Krazy Glue, a solar- powered calculator, Famous Publishers Books, and Matchbox "Around the World" cars. "Are you losing it, Mark? What is all this?" I told her of my experiment and my plans later on for the Krazy Glue and the cars. And it's not that she told me that this was to be our first and last date, but I inferred it from the lack of response to my subsequent twelve phone calls.

I'm sure Sarah told all her friends. And they told their friends, and so on. Because whenever I'm out in public, I get the strangest looks from women. As though they're thinking, "So you're the loser who took Sarah on the 99 Cent Only Store date." 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 Visa and MasterCard.

Nevertheless, life has a way of balancing itself out. I may have disappointed Sarah, but in my very next relationship, we both disappointed each other. How's that for balance in romance ...?

Love and Life on the Rebound

I was warned as a newly divorced man about the classic "rebound" relationship — one that shortly follows the ending of a previous one. Rebounders are supposedly needy, distressed, emotionally unavailable, and lacking the capacity to make good decisions about a partner. This not only describes me, but also most men I know in Los Angeles. Nothing personal, guys.

Still, I set out optimistically one night for a Jewish singles event called Opera under the Stars. Granted, I'm not a huge opera fan, nor am I a big stars nut, but it sounded classy and romantic and, okay, a friend talked me into going. The event's producer took over the backyard of a Brentwood home; brought in a tenor and a soprano to sing arias; served cheese, crackers, and wine at intermission; took our $30 admission charge; and wished us luck. Love for sale in L.A.

Luck appeared at intermission in the person of Amy, whom I immediately perceived as intelligent, attractive, funny, Jewish, available, and, most important, of course — interested in me.

The greatest benefit of an exciting new relationship? As any divorced man knows, going from a situation of infrequent sex and no sex — to one where you're suddenly with someone who actually wants to have frequent and enthusiastic sex with you. It's heaven, the life-saving oasis in your romance desert.

The abundant sex can also, of course, cloud one's vision, especially in conjunction with the aforementioned rebounder traits and the accompanying rose-colored glasses through which you're viewing your new object of desire. Those rose-hued glasses make it that much more challenging to make out the red flags directly in one's path. And so when Amy eventually suggested that I give up my writing aspirations and return to school to learn a trade, I said nothing.

Nor did I breathe a word of my disappointment one day when during our walk through an outdoor mall in Santa Monica, Amy looked around at our fellow mall-goers and disparagingly referred to them as "schleppers." Schlepper is a Yiddish term defined variously as an inept, stupid, ill-dressed, sloppy, and annoying person who always wants a bargain. It struck me as an incredibly rude, snobbish, and judgmental thing to say. But, again, I said nothing.

As the relationship developed, I kept my mouth shut about many of these kinds of things. Didn't want to rock the girlfriend boat. Preferred focusing on the things that were good, and there were good things, to be fair (Amy said to me on more than one occasion, "You're the man I've been searching for my whole life.") — that at the time I felt compensated for the insensitivities from "La Princesa," which is how Amy referred to herself.

My greatest regret about not speaking up was when my children invited me to join them at Passover seder at their mom's place. A little backstory: Although Amy was also divorced, she had no children. Didn't, in fact, seem all that taken with children and not especially eager to spend time with mine. Would even complain that on the nights I was having dinner with my children because she had to be eating all alone. By all this, did Amy expect me to not see my kids? Or to just have me feel guilty about her being alone?

In any case, Amy made it crystal clear that if I accepted that invitation rather than join her at her family's seder she would perceive it as a clear sign that I put her in second place — and our relationship would be over. I joined Amy at her family's seder, and to this day regret that decision.

Any man with just a bit of gumption and self-respect would have realized what was happening and walked away. But this is me we're talking about — the guy whose gumption was hidden behind his rebound relationship, his newfound sexual activity, and his rose-colored glasses.


Excerpted from "500 Dates"
by .
Copyright © 2015 Mark Miller.
Excerpted by permission of Skyhorse Publishing.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

Table of Contents

FOREWORD By Julie Spira, Publisher and Editor-in-Chief at Cyber-Dating Expert,
INTRODUCTION From King of the Dweebs to King of the Dates,
SECTION ONE: My 500 Dates,
Part A: I Dip a Novice Toe into the Dating Pool,
You Don't Have to Visit China to See Red Flags,
Dating Women I Can't Afford,
Does Dating Happiness Come From the Heart or the Wallet?,
Love and Life on the Rebound,
What's Love Got to Do with It?,
The Hottest Date I've Ever Had,
Making Scents of Being Single,
A Challenge to My Fellow Dating Cowards,
Part B: Look at Me — I'm a Dating Professional!,
Stop Me Before I Share Again!,
Dating? Think of It as Job Training,
I Confess: I Love Jewish Women!,
Unhappy New Year!,
How Not to Rock Your Date's World,
The Ghosts of Girlfriends Past,
Speed Loving: Recipe for Disaster,
Special Delivery,
Don't You Feel Happy When Your Friend Finds True Love?,
Do I Need a 12-Step Program for Serial Daters?,
Part C: Help! I'm Drowning in the Dating Ocean!,
I've Had 500 Dates — Kill Me Now,
Coffee Date's Hidden Thoughts — Revealed!,
Damn You, Foundation of Friendship!,
I'm Not Asking for the Moon and the Stars,
A Letter to My Future Soul Mate,
A Personal Invitation to Share My Dating Pain,
Help! My Girlfriend and Ex-Wife Are Hitting It Off!,
Writing is My Lady,
I Was a Woman's Last Online Dating Hope,
Finding a Soul Mate is a Numbers Game, Actually,
The Sounds of Dating Silence,
Death of a Relationship,
When the Music's Over,
The Less I See You, The More I Love You,
SECTION TWO: My Observations on Dating & Romance,
Whatever Happened to Woo?,
Mistakes Men Make in Romance,
A Woman's Guide to the Inner Workings of a Man's Brain,
How Internet Dating Beats the Pants Off Off-Line Dating!,
It's a Woman's World — We Men Only Date in It,
Thanksgivukkah: Not the Only Pairing That Can Benefit You Romantically,
Going for the Dating Gold,
Male-to-Female Dating Dictionary,
Never Underestimate the Importance of Proper Eye Contact,
Saying it without Words,
Oh, Come On, It'll Be Fun!,
Official Soul Mate Determination Test for Women Only,
Pillow Talk: A User's Guide,
Relationships 101,
How to Seduce a Jewish Woman,
Interpolitical Dating Tips,
Psssst, Men — Beware of These Potential Dating Disasters,
SECTION THREE: Dating Fantasies,
I Finally Found the Perfect Woman,
There Truly is Someone for Everyone,
Just Another Fairly Tale Romance,
The Continuing Adventures of Shlomo Rabinowitz: Jewish Private Eye & Dating Specialist,
Dating Boot Camp,
Skip Dating — Go Directly to Marriage,
SECTION FOUR: Fun "News" Stories I Wrote About Romance, Dating, and the Sexes,
Female God Recalls Man for Repairs,
5 Biggest Secrets Women Don't Want Men to Know,
Amish Phone Sex Chat Line a Huge Hit,
10 Best Opening Lines to Get Republican Women into Bed,
Spain Claims It Originated French Kissing — and Sues France for $6 Billion!,
Relatives Commit Woman for Dating Old Flame — an Actual Old Flame!,
Police Arrest Woman Who Claims She Simply Loved Her Boyfriend to Pieces!,
Couple Spontaneously Combust While Having Sex!,
Men's Least Effective Pickup Lines,
Woman Divorces Man After Discovering the "Mint" He Made Was Just Candy!,

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