Back in its heyday, ahead-of-its-time magazine Sassy (R.I.P.) had an amazing feature called “Cute Band Alert.” It extolled the finer qualities (Robert Smith hair, natty fashion sense, saving the whales) of a hard-working group worthy of more mainstream attention. The very least we can do is the same for our extremely dateable Simon & Schuster authors. This month we’re featuring Jack Gray, author of Pigeon in a Crosswalk, his must-read memoir about living single in New York City, eating doughnuts with his pal Kathy Griffin, and working as a producer for our beloved Anderson Cooper.
TOLL: Let’s just get the big bad one out of the way first. Why is a cute guy like you single, and what does that mean for the rest of us?
Jack: First of all, you’re only saying I’m cute because you saw my book jacket photo, which was like the one useable shot out of a thousand. Also, you’re clearly drunk. But, look, I don’t know—whatever the reason I’m single, it’s not for a lack of trying. I just haven’t had much luck. I might have to start writing my phone number on restaurant checks again.
TOLL: So not drunk. Yet. We always hear experts say that we put career ahead of our personal lives too much in New York. Do you agree? Is this killing our dating chances?
I think that’s kind of bullshit. However busy you are with your career, you can always make time for sex and brunch. At the same time, for all I care.
Where do you think you’re most likely to meet The One? We’re thinking the most cinematic meetup would be if you got picked up at Donut Pub on 14th Street here in the city, maybe at 3AM on Valentine’s Day. Or the only other person on earth who likes Planet Hollywood’s chicken fingers will be getting takeout at the same time you are, and BOOM.
As someone who has spent a lot of time at the Donut Pub, I can tell you there is not much of a singles scene. Unless you’re interested in making sweet, sweet love to a crueller, which I am.
As for Planet Hollywood, last time I checked, it was unfortunately closed for renovations. That said, if and when it reopens, someone wants to take me there for a date, I am totally down for that. I have a particular, dare I say sexy, way of shoveling their chicken fingers into my mouth.
We both love HBO’s Girls. What has that show done to illuminate your view on dating?
It’s illuminated my need to get Andrew Rannells’ e-mail address.
Not to throw words back in your face, but you told me that “dating sucks” and “at this point I’ll settle for lukewarm petting and episodes of Murder She Wrote.” Please explain.
Frankly, I’ll settle for a lot less. I’ll settle for an air kiss and a rerun of Magnum, P.I. And dating does suck. At least that would be my conclusion if I were able to get a date.
If Kathy Griffin wrote your online dating profile, what would it say?
“No one date him because he needs to be available to hang out with me at the Donut Pub all night.” She and I have logged more hours there than my fat jeans would like to acknowledge.
What is the one dating tactic you wish everyone would avoid?
Acting like they don’t want to eat the bread that comes before dinner.
You can read more about Jack’s love life and doughnut-diving adventures in his new book. Happy Valentine’s Day!
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