Getting Over the Dot-Com Don Juans

Cecilia, Jennifer and I were fleeing Gotham in a white

Rabbit convertible. Cecilia had never driven the car much further than the

Hamptons. But now, we were all suddenly unemployed and single. Top down, we

sped down Broome Street toward the Holland Tunnel, three women in our early

30’s singing, “Ain’t No Stopping Us Now!” and snapping digital photos, on our

way to New Orleans.

A few hours down the road, the exhaustion started to set in.

The three of us had each spent the past five years in the dot-com start-up

trenches. (Cecilia and Jennifer both founded successful dot-coms; I produced

Internet shows.) All three of us had had dreams which didn’t materialize. Paper

wealth that vanished. Cecilia recently shut her company down, which she

described as “so painful.” We had an unspoken agreement: no talk about work.

As the companies crashed, relationships fell apart, too. The

three of us were getting over relationships with dot-com chief executives. Like

a lot of women we know, we dated obsessively within the industry.

As we raced south on the Jersey Turnpike, I couldn’t stop

talking about my ex. Cecilia, Jennifer and everyone else I know are tired of

hearing about him. And I’m the last person on the planet who wants to talk

about him. I was embarrassed that he was on my mind. I was on a road trip with

two of the most generous friends a girl could have, and here I was dragging

them down with my delusional baggage.

“His Jewish nose,” I said, “I loved it. It reminded me of my


“Look, wildflowers!” Cecilia called out.

“I’m really going to miss the-”

“Pretty yellow flowers!” Cecilia said emphatically,

pointing, probably imagining that I was going to start talking about his cock.

“-synergy,” I said. “The brainstorming, the ideas.”

“Listen,” said Jennifer from the back seat. “It was a huge

turn-on to date people in the industry. Especially if you were workaholics like

we all were. I remember many nights hanging out at the Mercer after work with a

dot-com date. He’d be edgy. I’d say, ‘What’s wrong?’ He’d say, ‘My site isn’t

sticky; I’m losing too much traffic.’ I’d throw out three suggestions. He’d

relax, and I’d take him home for sex.

“You were dating someone in a tight-knit community where

everyone was obsessed with their work,” she continued. “We breathed and dreamed

the Internet. If we didn’t date our peers, we wouldn’t have had sex for six

years! But after the market crashed and the lights came on, you found yourself

with some flabby guy who’s basically a jerk and who cared more about losing his

money than he did about you. Get over it. Move on.”

But it was great while it lasted. The $750-a-plate benefit

dinners for Hillary Clinton. Being seated next to Anna Sui, Annie Leibovitz,

Goldie Hawn. Living in a loft. The maid came every other day. We never cooked.

Food arrived via Dean & DeLuca. Exotic cheeses. One day my ex came home

with 20 different kinds of toothpaste. Have you ever cleaned your teeth with

$20 toothpaste?

“And the parties!” said Cecilia. “Veuve Clicquot,

Nobu-catered spreads, dinner at Mercer Kitchen. And how about that fishing

trip, on a 60-foot boat with its own chef, masseuse and yoga instructor?”

“I introduced my ex to Zegna, Yohji Yamamoto and Richard

Tyler,” said Jennifer. “Then he started getting $120 haircuts.”

I started thinking of our current financial dilemmas. “You

know, our weekly unemployment checks will just barely cover a cut and color at

Laicale,” I said.

We all laughed nervously.

We sliced and diced our lives through New Jersey, Maryland

and the Carolinas. Welcome to Athens, Ga. Dave Matthews on the car stereo. We’d

be catching a Dave Matthews concert in New Orleans. We’d had many discussions

about Dave Matthews. His lyrics are so sensitive and sincere-qualities that

were lacking in the guys we knew. What kind of guys would show up at the

concert? We hoped for passionate lovers.

But I’m not quite done. My mind floats back to a recent

party, thrown by, where I bumped into Laurel Wells, former marketing

chick for SonicNet and, as she fled the building. “Gotta go home and

feed the cats!” she said. Inside, the thud of the music was annoying. A blonde

wearing a green bean suit was writhing on a platform. Some of my friends from

the past five years were standing around awkwardly: Marc Scarpa, the founder of

JumpCut; Rufus Griscom and Genevieve Field, the founders of, who used

to date; Nicholas Butterworth, who’s at MTVi and who never dates in the

industry; Craig Kanarick and Rebecca Odes, who founded a dot-com together and

got engaged. No one was really talking; we were all just gaping at each other.

Cecilia was sleeping in the back seat, curled up, looking

about 12. I was thinking about her recent boyfriend, basically a good guy, who

was shutting down his company.

I turned to Jennifer.

“How do you think the guys are feeling right now?” I said.

“Shitty,” she said. “Major psychological fallout. Think

about it: Many of them grew oversized egos to match their overinflated

companies. Imagine trying to squish a giant-sized ego back into a normal-sized

head. Internet guys used to imagine they could get laid all the time. Remember

back in 1999, when the guys started breaking up with us so they could date

models? The real problem is that most of them are broke. Now they’re selling

their lofts and Audis to pay for margins lost on the market. Some can’t even

pay the rent.”

Speaking of paying the rent, it was time to make our weekly

call to file our unemployment claims.

Cecilia had turned on her red Nokia.

“I got a signal!” she said. “Ready, set, go!”

Our three phones speed-dialed the same number. I heard the

familiar recording: “Welcome to the New York State Department of Labor’s

Tel-Service Line.”

“I got in!” I yelled.

“Me, too,” said Cecilia.

“Busy signal,” said Jennifer.

Two days later, outside the Dave Matthews concert, Jennifer

and I were killing time in the sweltering New Orleans sun. A woman who said she

knew voodoo was teaching us how to cast spells. I almost blew the week’s

unemployment check on 10 vials of “Swamp Power Potion.”

Inside, it turns out that Cecilia had tracked down three

shirtless and firm frat brothers: Chuck, Dion and Otter. Chuck was dancing

tantalizingly close behind me, singing into my ear as he rubbed a block of ice

on my shoulders. But he was too young! And so not my type! What was my type? He

whispered into my ear in a Southern drawl. Kind of adorable. He told me that he

was an entrepreneur. Uh, oh-not again. He explained: He and his buddies owned

Dough Boy Pizza in Biloxi, Miss. I told Cecilia and Jennifer; we were laughing.

“Dough Boy!” we said, now really laughing-not in a mean way, but with joy. Getting Over the Dot-Com Don Juans