Greetings, Cool Peeps:

Thanks for joining us today, Rob. You’re my first single male guest, so I’m excited to ask for your insight into the dating world. But, first, let’s learn a bit about you. I describe myself as snarky, overanalytical, and of course, picky. How would you describe yourself?

Oh, melancholy with a sense of humor, a loose cannon with a heart of gold, a “bad boy” for mild-mannered women.

You’ve done quite a bit of work as a medical writer. What are the pros and cons of the job? Any crazy stories about working with doctors?

I love medical writing because I love learning about the human body. I’ve also met my share of “mad doctors.” My favorite interview was with a renowned neurosurgeon nicknamed “J.R.” at a prestigious metropolitan teaching hospital. I should have known something was up when the director of communications said he wanted me to stop by his office after the interview. J.R. turned out to be a short guy about 60 years old who looked like a cocky sailor. His head was shaved, he had Navy tattoos on his arm, and he wore cowboy boots. He wore surgical scrubs, but they actually made him look like he belonged in a dish room somewhere, possibly a prison. On his desk was a picture of him with his buxom platinum blond wife on some kind of fishing expedition, her cleavage being the focal point of the photo. He put his cowboy boots up on his desk, blew a smoke ring toward the ceiling, and said, “Okay, let me tell you everything you want to know about this procedure.”

During the interview, I pictured him smoking in the operating room and flicking ashes into somebody’s skull. After the interview, I visited the director of communications, who wanted to know what I thought. “The first time I saw J.R., he was hanging out in the hallway, smoking a cigarette,” he said. “I almost said, ‘No smoking in the hallway, bub,’ but inexplicably thought the better of it. That’s why I still have my job.”

Your most recent book, The Yoga Divas and Other Stories combines your yoga experiences with your dating experiences. Please, tell us more about this book and how it came together.

I basically just amassed a number of yoga stories, but I didn’t think the collection was big enough to fill a whole book. So, I threw in a bunch of other autobiographical stories, from my quirky childhood, my days in the dish room at college, my mob super when I first got to New York, and the toxic cookout thrown by a member of my writer’s group.

Your first book, Tales of the Troupe, is about your experiences with a comedy troupe, Chucklehead, which took New York by storm in the 1980s. Tell us more about this book. Is it fact or fiction?

At first, I thought the book was all about comedy writing, but then one of my fellow writers said it’s really about this insular little group and how they interact. It’s almost entirely based on fact, though I embellished and I changed the names of all the people except my own. In “Bad Karma,” I combined my two serious screw-ups so that they occurred on the same night. I also made up a story called “I Rode With a Maniac,” about my friend Rick and I coming up against a bouncer in Sheepshead Bay. I made it up because it’s something Rick’s character would do, and I wanted the reader to get to know him better. One of the characters dies at the end, the troupe disbands, and we get an inkling that the narrator later got divorced. So, a lot of it is about learning about loss. I was a little concerned about what the troupe would think of the book, especially the actress I had a crush on. As it turns out, everybody loved it, including the actress.

You have an orange cat named Bongo and I have one named Captain Jack. Is your cat as good at judging the women in your life as mine is at judging the men in mine?

No, Bongo loves all women and all women know Bongo, so he’s not helpful in that department. Some of my women friends have private conversations with him and get miffed if I eavesdrop.

Okay, let’s get down to the nitty gritty, Rob. I personally hate to date, but I do it because I want an everlasting relationship. Does anyone really enjoy dating? Do you? What are the best and worst parts of dating?

I don’t like conventional dinner dates because they’re so forced, and I never know the so-called “dating rules,” including when the first kiss is warranted. I have enjoyed more leisurely dates, like one I had recently. We met online at, ahem, a senior dating site, and we walked her dogs at nearby Singing Beach. I found her completely engaging, so let’s keep our fingers crossed on that one!

I’ve had my fair share of dates, but I’ve never ventured into the online dating world. I hear a lot of horror stories but I also know of several success stories. So, tell us, do you ever peruse the ladies online? Any stories for us?

I do peruse the ladies online. I find some of the profiles unintentionally funny. One lady went on and on about how she couldn’t respond to the tons of e-mails she received—but she would let us know if she was interested. Another one bragged about her high I.Q. and the fact that she shares a Briggs-Myers profile with only 3% of the population. (Since the Briggs-Myers test assesses personality rather than intelligence, what she was essentially telling us was that she was incompatible with 97% of the population.)

Sometimes I think we are all destined to have bad dates because it’s the universe’s way of giving us common ground and better understanding of one another. (I told you I’m overanalytical.) So, please, tell us about some of your worst dates ever. We’re all ears.

The worst date I had was through a personal ad in the local paper. As soon as we sat down together, the conversation turned to kayaks. She had made one from scratch. She must have mistakenly thought I had asked her how to do that, because she launched into a very, very detailed description of the process. I was so bored, I started to hyperventilate. I tried to derail the conversation by making observations like, “You must be a very detail-oriented and driven person to do that,” but she kept steering it back to the process of making kayaks. Then she started describing her job and its unique challenges in exquisite detail. Three hours later, she suggested taking a stroll by the ocean, but I said, quite honestly. “No thank you. I’m really, really tired.”

If you were giving advice to women about how to best impress you (and men in general), what would that advice be? And be sure to tell us what to never do.

What never to do? Talk about yourself non-stop! I’m most impressed by women who are comfortable with themselves and know what makes them happy. As much as I’d like to make a woman happy, it’s ultimately not my job—it’s hers. This I’m adamant about: If she’s looking for a relationship to change her life, it’s time for me to run.

What is it about the fairer sex that baffles you the most?

Most of my best friends are women, and everything about them still baffles me. What baffles me the most is why women stay in relationships that do absolutely nothing for them. I’ve never understood the concept of being with someone just so as not to be alone.

What are the top five items on your To-Do list?

1. Get paid to write comedy. Check!
2. Publish my writing. Check!
3. Have a screenplay made into a movie.
4. Enter into a healthy, rewarding relationship.
5. Can’t say in mixed company! 😉

I’ve been forever called picky, but I maintain that we’re all picky creatures. What are you picky about?

I’m picky about food. I’ll eat most things, but I need a lot of variety. My favorite cuisines are Ethiopian, Thai, Vietnamese, and Indian. I’m also a little picky about women who don’t share my adventurous palate.

What project is next for Rob Dinsmoor?

I don’t know yet. Probably another collections of autobiographical stories about new weird adventures and revisiting old ones.

Any parting words for the masses? Any shameless plugs? Where can people you?

Both my books are available on Amazon.com as well as my website, You can also find my videos on YouTube (YogiRapper69). Thanks for the interview, Molly!

Rob Dinsmoor Website

Rob Dinsmoor Amazon

Rob Dinsmoor Twitter

Tags: bad dates, Briggs-Myers profiles, comedy writer, dating stories, humor writer, medical writing, online dating, personal ads, picky, rob dinsmoor, tales of the troupe, yoga divas, yoga teacher

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