Countdown to Bliss

Lara Kristin (Kris) Herndon and Ralph Lentini

Met: Fall 2003

Engaged: Feb. 7, 2004

Projected Wedding Date: Spring 2004

“I never, ever thought I’d get married. Ever,” said Kris Herndon, an ivory-skinned, raven-haired Atlanta-born belle, over a stiff Maker’s Mark and water at Donohue’s pub. “The idea of it freaked me out.”

For a while, her Southern friends thought this was cute-quirky, funny, very “New York.” Then she turned 30. “They start to think you’re ‘strange,'” said Ms. Herndon, now 33, a grant writer for the Paul Taylor Dance Company. “So in my last relationship”-with an antiques dealer-“I really tried to make an effort. But then I was about to introduce him to my parents, and I realized I just couldn’t do it.”

Then she met Ralph Lentini at a mutual friend’s birthday party on the Upper West Side. His parents had divorced when he was 16, and he’d been imagining himself as a lifetime bachelor. “It was just such a vicious divorce,” said Mr. Lentini, who works in sales at an investment bank. “In their whole marriage, there wasn’t one good moment. Ever.”

“We spent the whole night talking about how relationships are terrible,” Ms. Herndon said.

They also discussed the electric bass, which she had taken up recently. He’s played since he was little. “When you meet a girl, she might be really pretty and cool and great, but as a guy you always expect you’re going to have to drive the conversation,” said Mr. Lentini, 32. “But there she was, talking to me about bass gear! I was flipping out.” They ended the evening on the fire escape, playing moody Oasis and Beatles songs on a guitar à la Holly Golightly.

Their first date, at a Cuban place in Chelsea, ended awkwardly when Mr. Lentini borrowed the bathroom in Ms. Herndon’s nearby apartment, which she was sharing with her ex. But rendezvous No. 2, at Mercer Kitchen, was positively magical. “The waiters loved us! The people at tables near us loved us!” said the bespectacled, olive-skinned Mr. Lentini. “It was the best date of my life.”

Within a week he’d asked her to marry him via e-mail-just joshin’, of course.

But when he repeated the request one night six months later back at the Mercer, it was with a thick platinum and diamond eternity band from Stuart Moore. Ms. Herndon took the trinket and slid it on her finger without a word. “I took that as a positive sign,” Mr. Lentini said. Dinner was his treat, as is their custom. “I haven’t not paid yet,” bragged the old-fashioned fella. “I love it.”

They live on the Upper East Side and are planning either to elope or else to marry quietly at City Hall. “He’s the only person I’ve ever met who is chilled out enough for me,” Ms. Herndon said. And she had zero qualms about introducing him to the folks.

Jill Gaspar and Mark Higgins

Met: October 1999

Engaged: Sept. 22, 2001

Projected Wedding Date: March 20, 2004

Mark Higgins, a third-year law student at St. John’s and a researcher in Eliot Spitzer’s antitrust office who is also a dead ringer for a young Mr. Rogers, is marrying Jill Gaspar, a government contractor with a septum ring and a “quirky” personality to match. “It wasn’t like we first met and the clouds opened, you know?” he said. “It was just a progressive feeling of comfort with the other person till you realize the grass isn’t greener and what you have is a good thing.”

Both are 28 and attended Marist College (he transferred out sophomore year), but met only when they were introduced by a mutual friend at Madison’s Nite Club uptown. The Korean-born, feathered-haired Ms. Gaspar wrote her number on a cocktail napkin. Mr. Higgins, at the time a financial analyst, handed her his business card. She stuffed it in her pocket without a glance. “He goes, ‘That was really rude! You didn’t even look at it!'” she said. “So I pull it out finally and it says ‘financial analyst,’ so I’m like, ‘Oh-you’re a glorified secretary.’ And he’s like, ‘No, I’m important! They’ve given me a cell phone!'”

He used the prestigious gizmo to call her the next day as he was ordering takeout from Ottomanelli’s. “There was an uncanny ease over the phone within seconds,” he said. Enough that she felt comfortable asking him how long it had been since his last dental cleaning. (Two years.) “I don’t want to talk to people with bad dental hygiene,” she said.

But she braved a potential plaque onset, going for beer and pizza a week later at his place in Yorkville. Soon after that first date, Mr. Higgins went through a prolonged period of wanderlust. “I’m a gypsy!” he said. First, he did “financial-analyzing” for a year and a half in London. Then there was some work at a juvenile detention center in Guadalajara, Mexico. They visited each other every few months. Eventually he decided that his soul was thoroughly searched, bought a five-foot-long stuffed alligator, then returned to New York and presented it to Ms. Gaspar-along with tufts of cotton candy and a princess-cut diamond ring-over a birthday dinner at the Four Seasons. She was surprised-“I always thought I’d do a Kurt Russell/Goldie Hawn–type thing,” she said-but accepted readily enough.

They’ll be married back at the Seasons, with a hearty meal of duck and crab topped off with chocolate and vanilla cupcakes and Jacques Torres chocolates. (This will be followed by a big wedding feast in Portugal; Ms. Gaspar was adopted and raised by Portuguese immigrants in New Jersey.)

The bride will wear a strapless Vera Wang gown, accessorized with the aforementioned nose ring, which she’ll keep discreetly flipped up during the ceremony.

“Every person who has ever met me says, ‘Jill, you’re on a whole other planet,'” she said. “But Mark gets it: my weird mood swings, my far-out thoughts.”

Nadine Graham and Arie Kaplan

Met: September 1992

Engaged: May 16, 2003

Projected Wedding Date: May 30, 2004

Nadine Graham, 28, an almond-eyed playwright born in Jamaica, is marrying Arie Kaplan, 29, a freelance comedy writer for Mad and occasional Borscht Belt stand-up comic who looks like a cross between Alfred E. Newman and the actor Paul Giamatti. “We’re like Burns and Allen!” shouted Mr. Kaplan, seated beside his sweetie at Housing Works Café in Soho.

The pair is planning a Reform-Conservative Jewish wedding at the Huntington Town House in Long Island, with a kosher reception featuring reggae and klezmer. “My Bible is reruns of Saturday Night Live ,” Mr. Kaplan said. “But my brother’s a modern Orthodox.” Ms. Graham, raised a hodge-podge Christian, is converting. “I’d like to have kosher Jamaican food,” she said.

They got to know each other in French class at N.Y.U.’s Tisch School of the Arts, where they were both dramatic-writing majors. The bespectacled Mr. Kaplan was incredibly taken with Ms. Graham’s penchant for Yentl -esque floppy hats, but for some reason demurred when she asked if they could watch Dr. Strangelove together in his dorm room. “I’m an idiot,” he said. “I have no idea when girls are flirting with me.”

Three months later, he invited her to a screening of The Lion King , only to discover to his dismay that it was a screening of a film on the making of The Lion King . When the lights went down, he grabbed her hand, and by that evening’s study hall, the two were in full fondle. “We were sitting there and groping each other and making out and being really obnoxious,” she said.

The precocious Ms. Graham started college at 16; two years later, one of her plays, The Basement at the Bottom of the End of the World , was produced at the Joseph Papp Public Theater after winning a slot in Stephen Sondheim’s Young Playwrights Festival. In 1995, Essence magazine listed her as one of 25 Women Under 25 to Watch. “She was Lisa Simpson, but hotter,” Mr. Kaplan said.

She now works for the tax publishing company, Research Institute of America, and is writing a new screenplay, The Exotic Adventures of Dusky Jewel , about a black girl whose comic-strip character comes to life and inspires people toward civil disobedience. “She’s taken some time to reflect on the success of Basement , much like Tina Yothers of Family Ties ,” joked her pop-culture-addicted fiancé.

After college, they found a two-bedroom to share in Astoria. “We had our rocky times,” Ms. Graham said. In 1997, they broke up for nine months. In 1998, they split again. They tried to be just friends. “But it was kind of a sham,” she said, “because we were both still in love with each other.” By May of 2002 they were back in Astoria, this time in a three-bedroom with one roommate.

Over dinner at Café Centro on their ninth anniversary (“He decided when our anniversary was,” Ms. Graham said. “He’s the chronicler”), Mr. Kaplan presented her with a marquis-cut diamond with 12 round diamonds set in a yellow-gold band. “I had already been thinking of her as my wife,” he said. “I’m very goal-oriented. I pursue something until I’ve worn it down to a nub. That’s what I did with Nadine.”

-Ronda Kaysen