Countdown to Bliss

Steven Cloud and Ellie Jostad

Met: January 2000

Engaged. May 28, 2005

Projected Wedding Date: June 3, 2006

Ellie Jostad, 34, a boisterous, brunette editorial producer for the Nancy Grace show on CNN, plans to marry Steven Cloud, 32, a self-deprecating cartoonist with an impish grin and a loyal, nerdish fan base, in Ms. Jostad’s hometown of Brookings, S.D.

Their first meeting, an outing to see the comedy troupe the Kids in the Hall arranged by a mutual friend, was inauspicious. “I think I was annoyed with her,” said Mr. Cloud (just plain “Cloud” to his pals), over cheeseburgers and potato skins—ouch, our arteries!—at the Murray Hill tavern Molly’s.

“Really?!” Ms. Jostad said, sipping on a Guinness.

“I kind of felt like none of my jokes really made her laugh,” he said.

“You were really squirrelly back in those days,” Ms. Jostad said. “Trying too hard.”

At the time, Mr. Cloud was working as a creative director for Modem Media, an interactive ad agency in San Francisco. They’d wrangled backstage passes to the Kids show. “We were all staring at our shoes, star-struck or something,” he said.

On a subsequent date, they sat front and center at The Daily Show. “These are such good seats,” Mr. Cloud squealed, grabbing Ms. Jostad’s hand. When the producer returned to her East Village one-bedroom that night, she dialed a girlfriend to say, “I think I have a crush on him now.”

Several months later, the prospective couple accompanied their mutual friend and her new husband to a Britney Spears concert at Mandalay Bay in Las Vegas. “It’s so embarrassing,” Ms. Jostad said (we forgive you, honey!). When they got back to the hotel, Mr. Cloud’s face hovered temptingly near hers.

“I had no choice but to kiss you,” she said.

They began frequent cross-country visits. One memorable assignation involved Mr. Cloud, a noted pescaphobe, ordering soft-shell crab at the Red Cat in Chelsea. “The claws … and the smell!” he said. Other times they would meet in the flyover states, with Ms. Jostad organizing binders brimming with vital tourist information. “We were paying a lot of money on plane tickets,” she said. “It was pretty serious.”

After a year of this, Mr. Cloud found a no-fee apartment in Park Slope. His close proximity has changed the relationship, of course. “When you’re only seeing each other a couple times a month … ,” he said.

“People are on their best behavior,” Ms. Jostad interrupted.

“Right. You don’t get on each other’s nerves.”

“Are you saying I get on your nerves?”

“ Never!”

On the two-year anniversary of their first date in New York, Mr. Cloud made a reservation at the Red Cat. “Which immediately seemed suspicious,” said Ms. Jostad. Before dinner, he said, she gave him a pat-down.

“I did not!” she said. “I was giving you a hug.”

“She hugged me like a cop,” Mr. Cloud said.

But she failed to detect the 1920’s European-cut diamond, embellished with pavé, that he presented to her after dessert. There was no applause from the group of Eurotrash hipsters seated nearby. “They were staring at everyone with the same look of distaste,” said Ms. Jostad, amused.

John Botti and Donna Peitler

Met: Dec. 17, 1993

Engaged: Dec. 19, 2003

Projected Wedding Date: Dec. 17, 2005

It was the week before Christmas, and the city was blanketed in snow. John Botti, a hulking hedge-fund manager, was at J.F.K. airport with his father, Rocky, dropping off a soon-to-be ex-girlfriend.

After her delayed plane took off, father and son snuck into Austrian Airline’s first-class lounge in search of some stiff cocktails. Donna Peitler, an elegant brunette, was waitressing that day. She told the two men that she had spent over a year in Vienna. “You know, my son used to live in Europe,” the elder Mr. Botti said. “You should exchange phone numbers and meet up in New York sometime.”

Thanks, Pops!

Shortly thereafter, Mr. Botti fils suggested meeting Ms. Peitler at Rockefeller Center, though he had never skated before. She wound up doing figure eights around him. “I was worried about falling on my face,” he told The Love Beat. In more ways than one: Ms. Peitler was involved with someone else. The two decided to just be friends, meeting occasionally for dinner.

Six years later, when her relationship ended, it was Mr. Botti dating someone else (his father, sadly, died shortly after the Sept. 11 terrorist attacks). “I chased Donna for 10 years—that’s what I tell people,” he said, sitting with her at Le Figaro Café. “We didn’t actually kiss until 2002.”

“Oh, please,” said Ms. Peitler, 32, who now works as a freelance I.T. consultant.

During a stint in London, Mr. Botti returned to New York to be with his mother for the anniversary of Sept. 11. He gave Ms. Peitler a jingle, and she blew off her date and joined him for a chaste dinner at Serafina.

Then, as Thanksgiving approached, he invited her to go horseback riding in Newport, R.I. Definitely, thought Ms. Peitler.

As they approached their fancy B&B after a long day in the saddle, Mr. Botti gave her a card. “Wait in the car for 15 minutes,” it read.

When she entered their room, the tables were adorned with candles, the floor and bed with rose petals, Mr. Botti had just finished running a bath—and they hadn’t even kissed yet. Giddy-up, girlfriend!

One night, Mr. Botti went to the Plaza to secure a horse and carriage for … well, you know what. One in particular caught his eye. As he was making arrangements with the coachman, the horse started craning its head, as if eavesdropping.

“Good horse,” Mr. Botti said. “What’s its name?”

“Rocky,” said the coachman, Antonio.

Mr. Botti’s heart pounded suddenly. “It was the seal of approval, if you will,” he said. “If I were going to have any last-minute jitters, they were gone at that point.”

The next evening, he called his sweetie on the phone and told her to meet him at Rockefeller Center. “There’s a car service picking you up in 20 minutes,” he said.

“ Mmph,” replied Ms. Peitler, who’d been napping.

As they circled the ice, a man dropped to his knees and proposed to his girlfriend. “I’m looking at him and thinking, ‘Bastard! This is my night!’” Mr. Botti said. Ten minutes later, another guy dropped to his knees. Then a third. It was like a romantic-comedy parody.

When the announcement came for the ice to clear, Mr. Botti told Ms. Peitler to linger. The song “When You Know” from the movie Serendipity began playing over the loudspeakers, followed by an aria from the Tuscan tenor Andrea Bocelli, a favorite of theirs.

“You’re the woman of my dreams,” he declared, presenting her with an antique-style, platinum-set, emerald-cut diamond that he’d designed himself in Italy. “I will love you and take care of you forever. Will you marry me?”

After a victory lap around the rink before a cheering crowd, Rocky and Antonio escorted the couple to Daniel.

A month after their engagement, Ms. Peitler moved into Mr. Botti’s Upper East Side one-bedroom, near the park. Mr. Botti, who is 35, left his hedge fund to pursue other entrepreneurial endeavors, and he and Ms. Peitler took a trip around the world. “We’ve honeymooned before the honeymoon,” he said.

They will marry at the Church of Saint Ignatius Loyola, with a reception to follow at the Central Park Boathouse, featuring a chocolate truffle wedding cake by Sarabeth Levine.

At the end of the festivities, Rocky and Antonio will be waiting to take the newlyweds home. Countdown to Bliss