2004_09_tobybochan.jpgThe Basics
Age and occupation. How long have you lived here, where did you come from, and where do you live now?
I'm 29, editor at About.com, where I watch over the Home & Garden, Parenting, and Money channels, which is funny because I possess neither home, garden, kids, or money. I’m also finishing up a book, “The Badass Girl’s Guide to Poker,” which is coming out next May. I was born and bred on the Upper West Side, went to undergrad in Ann Arbor, MI, got an MFA in Austin, TX, and moved back to Manhattan in 2000. After two years in Washington Heights, I moved to the unhip side of Williamsburg last December.

Three Questions
1. You have a job overseeing content for a dotcom. Do you ever wake up thinking it's 1999?
Well, lately I’ve been partying like it’s 1989 and that does lead to some confusing mornings but… no, not really. If anything, it's more like working in a very premature archaeological dig. My first day at About, I looked through what my cube’s former occupant had left behind and found a promotional martini glass and shaker set. Around the office, there is evidence of its candyland past – Lava lamps, huge glass jars filled with red sour balls, a foosball table covered in cardboard -- that sort of thing. We do still get free bagels every Thursday.

2. Single again, you decided to sell your wedding dress online and appear in a New York Post dating competition. Neither ended with any visible success. How's the singles market these days?
First off, success is relative – I just wanted to be in the Post and convince my mother to let me donate the damn dress to charity, both of which I’ve accomplished. That said, it turns out I’m an idiot at dating – to be frank, I always have been, but being older and wiser isn’t helping. Half the time, I don’t even know if I’m on a date or not. It’s become sort of a running joke with my friends. The funny thing about it is, just after I recently declared that I was quitting the three-ring circus that is dating in this city, I heard I’m going to be in Esquire for a “Brutally Honest Personal” I submitted months ago.

3. One of your ambitions in life is to become the first woman to win the World Series of Poker. If you did, millions of people would know exactly how much money you'd won, including all your friends. How would you deal with the begging letters and freeloaders?
As anyone who plays in my regular game knows, I'm not that good. I've been playing poker since I was seven, but I've only started playing Texas Hold’em in January. The highest I’ve placed so far in a real tournament is 9th out of 151 – last year there were over 2,500 people at the WSOP. So I expect that if I make that final table, most of my winnings will be tied up trying to buy my soul back from the devil.

Proust-Krucoff Questionnaire
Please share a personal (and hopefully interesting) NYC taxi story.
My favorite taxi story actually happened on the 1 train about 10 years ago. I sat down across from a guy who was talking to another man wearing a Hawaiian shirt and shorts – and it was December. So Mr. Hawaii is very adamantly explaining how he gave up being a lawyer to become a taxi driver because, as he kept repeating, now he “really made a difference.” He got “people from point A to point B. Pregnant women, drunk people, everyone.” I was in a really annoying, carry-a-notebook-everywhere-and-write-down-everything phase of my writing life so I started transcribing the conversation. The best part was, Mr. Hawaii got off at 59th street and the man who had been talking to him, whom I had assumed knew him, looked right at me and shrugged. We both broke into insane laughter. Later, that taxi driver became the inspiration for one of the main characters in my first play.

9pm, Wednesday night - what are you doing?
I've just spent an hour of quality time with my celebrity boyfriend, Tom Welling, of Smallville.

Best celebrity sighting in New York, or personal experience with one if you're that type.
Gilda Radner taught me how to cartwheel.

Just after midnight on a Saturday - what are you doing?
I seem to be constantly celebrating one friend or another's 30th birthday at that time. Otherwise, playing poker.

What's the most expensive thing in your wardrobe?
I wish I were joking but I seriously have 2 dresses that were originally over $4000 that I’ve never worn. When I was in Texas, there was this Neiman Marcus Last Call that I was somewhat addicted to, and I kept buying these ridiculous cocktail dresses and justified it by thinking, Well, I’ll need these when I move back to New York. They're 99% off! I have this perpetual fantasy of being invited to fancy cocktail parties at the last minute.

Where do you summer?
Same place I sprung and will fall.

Just how much do you really love New York?
I want to have like, 10 million of its babies.

Medication: What and how much do you take?
I’ve somehow never been on medication. Go figure.

Of all the movies made about (or highly associated with) New York, what role would you have liked to be cast in?
I would have liked to be in Desperately Seeking Susan in the Rosanna Arquette role, so I could hang out with Madonna when she was still my idol.

If you could change one thing about New York, whatwould it be?
I'd build a casino on Governor's Island.

The End of The World is finally happening. Be it the Rapture, War of Armageddon, reversal of the Sun's magnetic field, or the Red Sox win the World Series. What are you going to do with your last 24 hours in NYC?
What’s funny is that freshman year of high school me and three of my girlfriends used to hang out at this Wendy’s and ask each other this very question. Hey, growing up in the city can't be exciting all the time. We all pretty much answered, lose our virginity, drink, do some drugs, and spend as much time possible with the people we loved. My answer hasn’t really changed much, though I’d be having sex with someone I loved. You know, to multitask.

For more Toby, visit her poker blog The Nut Heart Flush and a site with links to her writing. And the interview is by the inimitable Felix Salmon (many thanks).