The married Joel Stein goes on a date with Tiffany. After getting his wife's blessing, he tries for some extramarital credit with an ex-pop princess

By Joel Stein
Updated June 27, 2003 at 04:00 AM EDT
Credit: Joel Stein Column Illustration by Eric Palma

The married Joel Stein goes on a date with Tiffany

I wasn’t paying attention all the way through my wedding vows, but I don’t remember agreeing to anything about not dating. And when it comes to marriage contracts, I’m a strict constructionist. So while my wife, Cassandra, mentions how glad she is to not be ”out there” whenever we watch ”Blind Date,” I’m busy trying to devise a feasible scenario that’ll let me reenter a meat market where first-date etiquette now involves hot tubs and shed bikini tops. This, not a desire to dine with Ben Franklin, is why men dream about time machines.

So when E! offered to set me up with Dawn Wells, who played Mary Ann on ”Gilligan’s Island,” for their show ”Star Dates,” on which they pair celebrities with mortals, I was very excited. Hiding behind the excuses that this was ”for a column” and ”I was a Ginger guy,” I convinced Cassandra to concede. Then, Wells bailed and E! offered me pop starlet-cum-Playboy model Tiffany instead. When I ran that by Cassandra, I skipped every word between starlet and Tiffany. That’s because Tiffany, who I’ve had a thing for since the Mall Tour came to Jersey and got stuck there for several years, is the anti-Cassandra.

There’s always been a little tension in our relationship because I wasn’t instantaneously attracted to Cassandra when I first met her. You see, people often ask Cassandra if she’s a model or was born in Europe, and I usually prefer women who look like trashy sluts. And Tiffany may be many things, but she’s no European model.

After transferring the Dawn Wells go-ahead to Tiffany, I asked Cassandra what the ground rules were for my date. Sex was clearly out, though she momentarily waffled on kissing, which creeped me out in a Plato’s Retreat kind of way. Finally, I got her to acquiesce to footsie. ”Nobody has played footsie since junior high in the ’50s,” she said. ”You want to play footsie, go ahead and play footsie.” I was going to rub until my insteps bled. After a year of marriage, that’s as dirty as my dirty talk gets.

I met Tiffany at a Japanese restaurant in L.A. called Koi. I was surprisingly nervous for a guy who, at best, might get to toe wrestle. I think I was on edge not only because she was famous and there were cameras and I hadn’t been on a date in six and a half years but also because this was the stupidest thing I, or anyone else I know, had ever done.

Tiffany looked much better than she did in Playboy — like a short Julia Roberts with huge fake breasts, and I found her attractive even though I’m not into Julia Roberts. As we walked toward the restaurant’s secluded back room, she told me that she had come straight from arranging her uncle’s funeral, and all I could think was: ”Good. We’ll have something to talk about.” Right back in the dating saddle.

As the cameraman left his equipment on autopilot, and every waiter in the restaurant stopped by in hopes of getting discovered, our conversation went pretty well. We touched all the basic date bases, like siblings, exes, how stupid it is to tattoo your high school boyfriend’s name on your ankle, and how Playboy’s makeup artists touch up your freshly groomed body hair with a mascara brush. If that isn’t hot-tub talk, I don’t know what is.

As waiters from neighboring restaurants started to come over, I came to an end-of-date realization: Even if I were single, Tiffany would have never gone on a second date. I could tell because she said that if I were single, she’d set me up with a friend. I pick up on subtle stuff like that. Until that moment, I’d actually believed something my dear, sweet wife had convinced me of: that, despite decades’ worth of evidence to the contrary, every woman wants me. The reality is that I could never get a woman like Tiffany, let alone any pop star currently in rotation. It has something to do with my lack of manliness, edge, and style, but mostly because I’m not that good-looking. They removed that cartoon of me up in the corner for a reason.

Luckily, E! lost the footage of my Tiffany date — along with God knows how many ”Wild On”s posterity will now be deprived of — so it will never air. And Cassandra will never truly know how other women feel about me. Which basically sums up my whole marriage strategy: Act cocky and hope she doesn’t figure out how lucky I am that she sticks around.