Countdown to Bliss

Kelly McMasters and Mark Milroy

Met: Oct. 12, 2000 Engaged: Dec. 27, 2003 Projected Wedding Date: May 21, 2005

It was over a plate of sloppy Mexican corn at Café Habana that Kelly McMasters first stared into the smoky eyes of Mark Milroy and realized that she’d found her soul mate. At first, she feared the flutter in her stomach was an adverse reaction to the cheese; however, she soon realized that what she was feeling wasn’t lactose intolerance but love.

The couple first locked eyes over whiskey, introduced by a mutual friend at the so-called Relish Diner (really more of a bar) in Williamsburg. Mr. Milroy, a Brooklyn-based artist, was enchanted when Ms. McMasters, who is 5-foot-5 with a blonde pixie cut, bounded into the room. I need a girl like that, he thought. “It was one of those ridiculously romantic, schmoopy moments where the whole world stepped back and it was just us,” she said.

The next day, the hipster artist e-mailed their mutual friend for Ms. McMasters’ contact info, but because she was in a relationship, the message was never delivered. But the two thought of each other longingly over the following three months, and when Ms. McMasters’ relationship went bust, her mother suggested a blitzkrieg week of dating. “He was my Wednesday,” said the young Irish belle, 28.

“Our first few conversations were marathon,” said Mr. Milroy, 37. “I had to see her, and she kept saying she was busy. It was because she had all these other dates.” Drinks at Von were followed by the aforementioned sloppy corn, and Ms. McMasters cancelled the rest of her assignations.

Then the couple passed their first major trial: They saw each other’s work. “I was terrified to walk into his studio that first time,” said Ms. McMasters, then an editor at AOL Digital City. “I thought, ‘Oh my God, another Williamsburg artist.'” Fortunately, his paintings found favor. “It was such a relief,” she said, “I knew … if I didn’t like his art, it would never work.” Ultimately, his autonomy inspired her to quit her job and pursue a career in freelance writing.

One day, Mr. Milroy ambled past Doyle and Doyle, a Lower East Side shop specializing in antique and estate jewelry. The store was closed but the lights were on, so he pushed the door open. Almost immediately, he spotted a platinum-set 1.5-carat Asscher-cut diamond from the 1930’s. He found it “so Kelly,” Mr. Milroy said. “It’s not ostentatious in its beauty; it’s subtle; it doesn’t try to be anything it’s not. I saw it and was like, ‘Holy crap-now I have to propose.'”

They were lounging on the beach while visiting her parents in Florida when he decided to toy with her a bit.

“Do we really need a ring to get married?” Mr. Milroy asked.

“Yes,” Ms. McMasters replied. “It doesn’t have to be a diamond, but something to show you really made a commitment.”

He pulled a box out from beneath his swimming trunks. “How’s this?” he said.

Ms. McMasters spent the next three days crying, on and off.

The ring has inspired plans for a 1940’s-themed wedding at the National Arts Club, where Mr. Milroy works part-time as a drawing instructor (“My mom always said, ‘She’s not marrying you for the money,'” he recalled).

“It’s like walking into a Fitzgerald novel,” cooed Ms. McMasters, who is trying to organize the whole shebang with only her fiancé’s help. “I always thought those girls were so silly, making it sound like a full-time job,” she added. “But it really is.”

Kristen von Summer and David Waldorf

Met: September 2003 Engaged: Feb. 1, 2005 Projected Wedding Date: July 23, 2005

President George W. Bush was visiting New York, and Kristen von Summer was sitting fuming behind the wheel of her sister’s red Ford Explorer, stuck in the gridlocked traffic near the corner of 66th and Broadway, when she suddenly noticed a tall, handsome man ditch his cab and make a dash for the nearby subway.

In an instant, she realized it was a guy she’d been e-mailing with for weeks on Match.com: “nyccanuck541.” They hadn’t yet met in the flesh. “I just knew it was him,” she said. “But I didn’t even know his name yet.”

Ms. von Summer, a former model who now runs her family’s commercial real-estate business, had plunged into online dating after 12 years on the Manhattan singles scene. “I wanted to meet a good guy,” she said. “A guy who wanted to get married and have kids.” And the 6-foot-5, fair-haired and blue-eyed Mr. Waldorf seemed like a good candidate to help her produce a flock of little Amazons. “I’ve always been a ‘height-ist,'” she said. “He just had that manly and rugged look that you never see in New York.”

Mr. Waldorf, a recent import from Toronto who’d recently separated from his wife (and no relation to our famous hotel), was relieved to find this 5-foot-10 fair-skinned brunette online. “I had been here about eight months and figured there was eight million people in this city,” he said. “How on earth had I not met anyone?”

The two arranged a first date at the Central Park Zoo. Ms. von Summer didn’t mention that she had already espied Mr. Waldorf in the flesh. “I didn’t want him to think I was stalking him or anything,” she said. They had each sworn to be first to end the evening, but wound up prolonging their date with drinks at the Boathouse.

A week later, he took her to a Bruce Springsteen concert and made pumpkin soup and pasta with a creamy red sauce for her at his Upper West Side apartment. “He’d not been in New York for very long,” laughed Ms. von Summer, 37.

But though Mr. Waldorf “knew pretty early on that Kristin was something special,” both were hesitant to declare that they’d met their Match. “I knew he was dating,” Ms. von Summer said. “I’d go online and see that he had been ‘active.'” She forced herself to see a few other men, but it just “sent me screaming back to David,” she said.

After 15 months of courtship, Mr. Waldorf, 44, moved into her pad on the Upper West Side (since then, they’ve moved on up to the East Side). “I had wanted to marry her for a while,” he said, but the paperwork for his divorce still hadn’t come through.

When it did, he announced a midwinter trip to Florida. During a snorkel off the Keys, Mr. Waldorf whipped out a slate upon which he’d written “Will you marry me?” along with a pair of boxes to indicate her response: “Yes” or “No.” Their long legs flapping in the 20-foot-deep waters, Ms. von Summer eagerly checked the “Yes” box. When they were submerged, he gave her a large, cushion-cut, pavé-surrounded diamond set in platinum. “I saw two sharks, some eels and a barracuda,” reported Mr. Waldorf. “She stared at the ring for the next 50 minutes.”

They’ll marry at the von Summers’ 44-acre estate in Warren, Vt.

-Sara Vilkomerson

Born Yesterday

Justin Patrick Kloiber

April 30, 2005 12:40 a.m. 8 pounds, 6 ounces St. Vincent’s Hospital

Rick and Jill Kloiber inaugurated their six-year relationship at a Willie Nelson concert, so imagine their delight when Ms. Kloiber, 33, delivered the couple’s firstborn on the country singer’s birthday (she ate hot peppers to encourage the coincidence). Little Justin even has the peepers to match Willie’s famous hit, “Blue Eyes Crying in the Rain.” “He came out nice and pink,” said Mom, the advertising director at ELLEgirl magazine. “We were afraid he would be one of those slimy babies.” Mr. Kloiber, 36, is an account executive at Fox, but he clearly has no such “establishment” ambitions for his small son, who will be sleeping under photographs of … you guessed it.