Met: November 1999

Engaged: December 2003

Projected Wedding Date: 2006

The wedding party was driving through Bangkok in a pimped-out double-decker tour bus (leopard-print seats, a pink curtain on the windows). “It looked like Snoop Dogg’s grandma decorated this tour bus,” said Clayton Cubitt, 33, a freelance photographer who was documenting the big event with his girlfriend, Katie Wedlund. Family members were doling out thanks on a microphone, and the mother of the bride asked Mr. Cubitt to stand up and say something.

“I want to thank Katie for being a wonderful assistant on the trip,” Mr. Cubitt said, gazing at her, “for being my muse and my best friend, and if she’ll have me … my wife!” The bus broke out in cheers, and Ms. Wedlund stood up and started screaming. “She was running down the aisle like it was The Price Is Right or something,” said Mr. Cubitt, sitting with his fiancée and a green-tea latte at Supercore in Williamsburg, just blocks from their spacious two-bedroom apartment. The proposal was spontaneous. “I just felt this strong connection with her—just this fundamental rightness,” he said.

When the couple got off the bus, they went shopping for a set of silver-spiked brass knuckles. “Not to sound too crude—not to degrade the romantic aspect of it—but an engagement ring is what?” asked Mr. Cubitt, who was wearing frayed, fingerless gloves. “It’s essentially you peeing on your territory. It’s a way to mark your lover, to say she’s accounted for. What better way to ward off potential suitors than with brass knuckles?”

“It’s exactly how I’d want it,” crowed Ms. Wedlund, a bespectacled makeup artist with a choppy brown ’do who just turned 35. (“Or as someone called it this weekend: dirty-five.”)

The unconventional pair first met at a photo shoot in Ms. Wedlund’s hometown of Minneapolis. She was an hour late, but Mr. Cubitt found her witty and charming. “And the big butt didn’t hurt,” he said. They exchanged cards.

The next day, Ms. Wedlund moved to a share in Park Slope. Three months later, Mr. Cubitt visited and they began a long-distance friends-with-benefits deal, which continued after Mr. Cubitt found an apartment in Hell’s Kitchen a year later. They regarded their relationship as “dating”; he had an ex in Minneapolis, with an option to renew. “I was madly in love with him,” Ms. Wedlund said, “but I couldn’t let that out.”

She expressed her frustration through a one-night stand with an Austrian man she met at a party, which she announced to Mr. Cubitt the next morning. “I was surprised,” he said. “It’d be like if I popped out and said, ‘Oh, I voted Republican yesterday.’ It was odd.”

Ms. Wedlund wrote him a letter. “If I was jumping out of a plane, and I had to say something to you,” it read—a scenario he had posed before, which she had refused to entertain—“it would be ‘I love you.’” Scanning the words over her shoulder as she sat at the computer, he leaned in to repeat them back to her.

They were mulling a wedding in Mr. Cubitt’s hometown of New Orleans before Hurricane Katrina hit, upending the trailer he’d recently bought his mother and little brother. The couple promptly traveled to New Orleans to support the family and photograph the devastation. A picture of his mom sitting on a pile of rubble was picked up by Rolling Stone.

“You really need to get that girl a ring for Christmas,” Mrs. Cubitt told her son on a recent visit. Craving grandchildren, she has threatened to poke a hole in Ms. Wedlund’s diaphragm. “I’m like, ‘What is this, 1968?’” said Mr. Cubitt. “Who uses a diaphragm?”

Kristine Cooney and Steven Kaufman

Met: April 2002

Engaged: July 18, 2004

Projected Wedding Date: Oct. 8, 2006

Nothing like a man in uniform! Kristine Cooney, 27, a pouty-lipped brunette first-grade teacher at the Mary Queen of Heaven School in Brooklyn, plans to marry Steven Kaufman, 30, a muscular security guard at New York Methodist Hospital. Both a rabbi and a priest will supervise the ceremony, to be held at the Grand Plaza in Staten Island. The couple plans to move in together after their wedding.

A mutual friend described Mr. Kaufman to Ms. Cooney as sweet, outgoing and a snappy dresser, and they began exchanging e-mails. One day, after playing a game of computer solitaire at the house she was sharing with her mother in Marine Park, Ms. Cooney decided to be brave and call him up.

“Who’s this?” he demanded, answering the phone in his thick Brooklynese.

“Who’s this?” she retorted. The connection was immediate. Though Mr. Kaufman had said in one e-mail that he “wasn’t good at talking on the phone,” the two of them managed to gab for four hours, ultimately agreeing to meet the following weekend at the Wicked Monk, a bar in Bay Ridge.

Each showed up with a wing person and a code for immediate departure. If the date didn’t go well, Ms. Cooney planned to turn to her friend and say, “The M&M’s are swimming!” (Huh?) Mr. Kaufman was just going to announce coldly: “I’m going to a different bar.”

Luckily, it went well.

The next evening, Mr. Kaufman went to Ms. Cooney’s house to hang out. Standing on the stoop, a step below the diminutive demoiselle, he leaned in and planted a smooch on her lips. “A nice little kiss,” he remembered, sitting with his fiancée at a Starbucks in Times Square. “Not romantic romantic, but a kiss she would never forget.”

“I didn’t forget,” cooed Ms. Cooney, scrunching her nose.

“Twins run in my family,” she told him that very night. “Are you O.K. with having twins?” (Yikes!)

“Oh my God, what are you doing?” Mr. Kaufman said. “It’s only been one date.”

But Ms. Cooney belongs to that new breed of New York woman who knows just what she wants in a relationship and isn’t afraid to declare it. “I knew after the third date that I was going to wind up marrying him,” she said.

Throughout their courtship, she continued to drop little “hints,” many of which began, “When we’re married …. ” Finally, Mr. Kaufman told her that he would add a seven-day delay to his proposal every time she hounded him.

“It got to like 800 days,” he said.

“I was just so sure,” Ms. Cooney said. “He was sure, too, though he was busting my chops.”

Two years after they met, during a gondola ride in two-foot-deep water at the Venetian Hotel in Las Vegas, Ms. Cooney had a sudden premonition and switched the ring that was on her left-hand ring finger to her right. “I didn’t expect it,” she said, meaning a proposal, “but I thought, ‘If it’s going to be on this trip, it’s going to be on this ride.’”

Sure enough, it wasn’t long before Mr. Kaufman ordered Salvatorio, the gondolier, to pull over. “I feel sick,” Mr. Kaufman said, then slid to one knee.

“I’ve been waiting for this moment for a very long time,” he said. “I love you so much, and I want to be with you for the rest of my life …. Will you marry me?” He pulled out an antique ring that had belonged to Ms. Cooney’s maternal grandmother: a circa-1940’s single-carat, round-cut diamond in a square platinum setting, with an embellished platinum band and two pavé diamonds. Bada-bing!

Ms. Cooney hid her face in her hands and began to cry.

“Babe,” Mr. Kaufman said gently, “you going to say yes?”

“Yes,” she said.

“She said yes!” hollered Salvatorio to a crowd of gawkers who’d been momentarily distracted from their gambling.

“I was getting older,” said Mr. Kaufman, explaining his decision to propose. “I wanted to have my life settled; I wanted to have a family.”

“You didn’t want to let me get away,” Ms. Cooney said. The groom-to-be stuck out his tongue at her.