The Man Who Patents His Breakups: Brian Donovan, Author of ‘Not a Match’

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Brian Donovan doesn’t do things halfway. When the comedian and writer, who has written for the likes of Vh1, Thought Catalog, Comedy Central and NPR, found himself single and unhappy about it, he went looking for his next love story with a vengeance. Over 100 online dates later, he emerged with enough material (and emotional baggage) to write a book. Thus was born Not A Match: My True Tales of Online Dating Disasters, which is currently #1 in the Love & Romance section of the Kindle Store.

Given that we have a certain pointed interest in online dating, we reached out to Brian to get the story behind the story.

For this book you went on many, many dates and had many, many bad experiences. What kept you going, made you leave the house on that 85th date? Was it the book? Was it habit? An unshakeable desire to meet your soulmate? None of the above?

I know this is the sort of preposterous thing that Tom Hanks would say to Meg Ryan in a movie and make everyone throw up in their popcorn, but truly, I was looking for the love of my life. I’m a writer, which means two things: I’m good with the written word, and I’m wildly awkward in public — so internet dating was a good fit for me. I could approach women online and totally edit out all the stammering and goofiness that would happen if I did it in a bar or on the subway. And after a certain amount of time, I got pretty good at it, so I could write (moderately) charming emails and know that I could have a couple of fairly promising dates a week. Of course, that promise often ended up in disaster, but without that, there wouldn’t be a book. So, win some lose some.

And no, I can proudly say that I never went on a single date with the book, or my website, in mind. All attempts at romance were earnest and true. I’d feel like too much of a jerk otherwise.

While we get hilarious accounts of the women you meet, you don’t reveal a ton of information about yourself. Who are you? How old? Where did you grow up? What’s your biggest goal in life? 

Oh, I’m really quite boring. I’m 34, was born in Boston (Go Red Sox/Patriots/Celtics!), went to school in DC, and then moved to New York where I was an actor, writer, and comedian. I was really lucky, because in NYC I got accomplish a lot of things I’d always dreamed of. I performed in several extended runs at the UCB Theater, which had been a dream of mine since college. My writing appeared on Late Night with Jimmy Fallon and Chappelle’s Show– which was amazing because I’d been obsessed with late night TV and sketch comedy since elementary school. And I acted in a sold-out off-Broadway run of a brilliant play called Thom Pain: (Based on Nothing). All of those things were amazing, and they helped balance out the epic nightmare that was my love life at the time. My biggest goal has always been to create my own TV show, something my writing partner and I are getting closer to everyday, which is really exciting. Oh, and another lifelong goal is making the perfect peanut butter and jelly sandwich. IT’S SO EASY TO GO OVERBOARD ON THE JELLY!!!

Let’s talk breakups. There were many. You even patented a few, including the “Have Sex While Being Cried On For a While, Get Yelled at For Not Delivering Orgasms Under Those Conditions, Then Initiating a Break-Up With a Girl You’re Not  Even Officially Dating While She Pretends to Keep Reading Her Book” break up. What was the worst way you were broken up with? The worst way you dumped someone?

Hmmm. The worst way I was dumped. So many choices! Probably the winner would be the first real relationship I got from online dating. We dated for several months, and I was really falling for this girl, until one night, at around midnight, she sent me an email saying, “We have to break up. This isn’t working for me. But I really hate talking about these sorts of things, so please don’t write, or call, or show up at my apartment, or text. I won’t answer. Goodbye” And you know what, she held true to her word – completely ignoring me with no explanation whatsoever. It was heartbreaking. However, the story had a pleasant ending, as a few months later I ran into her roommate in a bar and she told me: “Oh, after she dated you, Danielle got serious with a guy who lived in a shack.” That’s when you know you’ve won the breakup, when the next guy she dates is someone without electricity or running water. Yippee!

Let’s be honest – how many date disasters do you think were the fault of the woman? I mean, there was only 1 common denominator on every date (just sayin…).

Oh, believe me, I think I play a large role in all of these disasters. I’m the one who’s selecting these women, and going on these dates, and sticking with things far past the point any reasonable person would. And probably making them a little nuts with my general, innate lunacy. But truly, I don’t really think “fault” has anything to do with it. None of these women were malicious, not the girl who cried when we had sex, or the one who caught on fire, on the girl who brought her boyfriend on our first date. They were just doing their best in complicated circumstances. As was I. No one tries to be crazy; it just sometimes turns out that way. It’s not a matter or fault; it’s strictly an issue of funny. And thankfully for readers, I’ve experienced a lot of things that are very, very funny. Thankfully for my shrink too, as my therapy has likely paid for two or three summer homes by this point.

Your never-fail date conversation starter is: “Would you have sex with a dead person for five seconds if it meant getting free laundry for the rest of your life?” How’d you come up with this one? 

Actually, that started as a bar conversation. The kind of thing you come up with in New York, where you’re allowed to drink until 4 AM, and doing it on a Tuesday night is not at all unconventional. A friend was talking about how much he hated doing his laundry, and we tried to see what was the worst thing he would do to never have to clean his clothes ever again. Kill another human being? No, that’s way too far. Eat a handful of bugs? Turns out, that’s not far enough. The perfect test, and a question that rattled from our table to every other in the bar that night was, “Would you have 5 seconds of intercourse with a corpse in exchange for never having to do laundry again.” The great thing is the results are pretty close to 50-50. For every person that looks at you horrified and offended, another says “Absolutely! I hate pairing up my stupid socks!” So after a while, I started trotting it out on dates that weren’t going well. It always livened things up, I’ll tell you that! And only once did a woman walk out in disgust. Again, Yippee!

You discuss the plight of one of the most targeted groups in online dating: short men. They get a rough break. You acknowledge that your research isn’t firsthand (“I’ll admit that I don’t know a ton about this issue, because I’m 6’2.” That’s right, ladies! If you ignore the fact that I write books about all my dates, I’m a real catch!”) but you’ve spent plenty of time pondering the subject. Why do women not prefer short men? And what can short men do about it?

If I knew the answer to that, I’d be the King of Shortlandia. As I discuss in the book, I raised this issue on my site,, and got hundreds of email responses. For the most part, women said they liked feeling smaller than their date, surrounded, or subconsciously protected by their mate’s size. That’s not my opinion; it’s just what I was told. And therefor, a guy who’s smaller than them just makes them feel weird, too big, and a little awkward. What can short guys do about it? Uh….carry around a step stool? Devise an elaborate system of lights and mirrors to appear 6’1″ wherever they go? No idea. They’re screwed. It’s one of the few things about a person that can’t be fixed, and I feel for the short fellahs every day. They got a raw deal.

Let’s turn to the rules of online dating. You take a controversial stance on messaging someone twice – specifically, you say it’s ok, if a woman doesn’t respond to your initial message, to send her another one. Does this work? Is there a right way/wrong way to do it?

Sure, I mean, what’s the worst thing that can happen? She’s not gonna write you back again? Who cares. That’s the great thing about Internet dating: there really are no negative repercussions. So they don’t like what you wrote, who cares? You’ll never hear from them again. They’re a stranger. I already never hear from strangers–that’s why they’re strangers to be begin with! So no harm, no foul. I absolutely think, if you’re particularly taken with someone, you should email them a second time. The key to the message is admitting that you know second emails are a little kooky, but you couldn’t resist. Now, how exactly do you pull that off? Well you’ll just have to buy the book and find out!

Lessons: What did you learn about online dating? What’s your biggest advice to someone who is doing this because they really truly want (and believe they can find) their life partner online?

My biggest piece of advice is to stick with it. Internet dating is a numbers game, and if one date doesn’t go well, don’t get discouraged. Keep at it, and don’t feel bad if someone doesn’t respond to your note, or if you don’t hit it off in person. You’re dealing with a complete stranger, the likelihood that it’s going to be goodnight kisses and wedding bell romance every time is extremely low. Like…pathetically, horrifyingly low. But if you keep taking swings, sooner or later you’ll hit a home run. Or at least, a very respectable single.

What’s next for you? Are you seeing anyone? Does she know about the book?

Yes, I’m dating someone now, who, as a matter of fact, I met on OkCupid. She knows about the book, and although me writing about my dating is certainly not her favorite thing in the world, she’s very supportive, and extremely exciting about all the success the book has had. As is usually the case with us guys, she is far better than I actually deserve.

Not a Match: My True Tales of Online Dating Disasters is an Amazon Bestseller and a selection to their prestigious Kindle Select collection. You can buy it here. Please follow Brian Donovan at @thebriandonovan, and check out his dating website on which the book is based, It’s Not a