Met: Fall 1999

Engaged: Aug. 26, 2005

Projected Wedding Date: Oct. 21, 2006

Daniella Farber was sipping on a raspberry Stoli and tonic at Dewey’s Flatiron when she spotted Jason Schwartz, a chum from the University of Michigan and an old acquaintance of her ex, coiffed as only an investment banker could be. They struck up a conversation over a game of pool and found out that they both lived in Windsor Court, the dorm-like apartment complex in Murray Hill.

Over the following month, the buff banker, then working for Credit Suisse First Boston, began visiting Ms. Farber’s apartment for late-night games of Scrabble. “She’s excellent at it,” Mr. Schwartz said proudly. He’d tuck her into bed chastely, then go back to work.

Ms. Farber, a former managing editor of The Observer’s advertorial sections, first realized that she’d been bitten by the love bug when she found herself stymied about what to wear to the birthday party of a mutual friend. “I’m the type of girl that would put on one outfit and go out the door,” she said. “When he would come home from work, I’d be in my pajamas with my hair in a ponytail.”

Apparently, her choice of party outfit went over well. “I really like you,” confessed Mr. Schwartz, swooping in for a kiss as he walked her home afterward. “It was really juvenile,” said Ms. Farber, 26, who is petite with highlighted brown hair. “Since we were such good friends, we were both nervous to have anything awkward between us.” He asked her for a proper date later that week, promptly calling all of his friends for the perfect restaurant recommendation. “I wanted this one to be really special, but I didn’t want it to be overkill—not like Tao,” said Mr. Schwartz, 27. “I like to think of myself as a human Zagat.”

He settled on Firenze, an Italian place on the Upper East Side with low lighting and plenty of private nooks. Soon afterward, the late-night bed tuck-ins began getting a bit naughtier.

“I have something to tell you, but I don’t want you to say a word, no matter how you feel,” Ms. Farber boldly told him across the pillow as Valentine’s Day approached. “I think I’m falling in love with you.”

“I’m not allowed to respond?” Mr. Schwartz said.

“No.”

He waited a month to echo the sentiment. “I didn’t want her to think I was just saying it because she just said it to me,” he said.

About three years into their relationship, Mr. Schwartz moved to Philadelphia (the sixth borough, we hear) to attend business school at Wharton, while Ms. Farber moved to a converted two-bedroom on the Upper East Side. But “I couldn’t be there without him,” she said.

After a year of torturous long-distance romance, she quit The Observer and got a job as a retail associate at Plage Tahiti in Philly, where the couple now lives an exciting life featuring plenty of ping-pong and card games (needless to say, they don’t plan to stay). But “this year is so much better,” Mr. Schwartz said, “because essentially every night I can go home and snuggle with her.” Awww ….

He proposed before she relocated, during a romantic getaway to the Montauk Manor, using a custom-made jigsaw puzzle of a boy kneeling next to a girl. “Oh, we’re missing pieces!” Ms. Farber said as she attempted to assemble it.

“I’ll see if there are any left in the box,” said Mr. Schwartz craftily, handing her a piece that read “Daniella, will you marry me?” Then he dropped to one knee himself and pulled out a fat oval diamond, flanked by two pear-shaped ones and set in platinum—designed with the help of Burdeen’s, a jeweler in Chicago.

They will marry at the Brae Burn Country Club in Purchase, N.Y., near Ms. Farber’s hometown.

“I really don’t remember my world before him,” said the bride-to-be.

Laura Brown and Chris Gray

Met: October 1998

Engaged: Nov. 26, 2005

Projected Wedding Date: Summer 2006

“I always wanted to live in New York,” said Laura Brown, 39, a button-nosed Arkansas native and former Berkeley resident who works in the special-markets department for Ryko, the record company. “I wasn’t happy in California. And, of course, he was a sidebar.”

“He” is her fiancé, Chris Gray, 34, a managing director at Recall Records whom she plans to marry (thereby offering her a choice of neutral surnames) at an as-yet-undetermined location. They’re currently living in separate Williamsburg apartments, but at the end of the month she’ll move down the street to his one-bedroom, bringing a much-needed television along with her.

The couple met during a label meeting at the Grapevine, a restaurant in Salem, Mass.—“the only decent one,” Mr. Gray said, sitting recently in a Starbucks at Union Square. Befitting her hipster job, Ms. Brown was wearing John Fluevog loafers. “I remember looking down at her shoes and thinking, I could hang out with her,” said Mr. Gray, who himself favors sideburns and plaid.

At the time, he was label manager for Hannibal Records (part of Ryko). “He’s a really important person in the business,” a mutual friend told Ms. Brown. She envisioned a silver-haired music executive and was astonished that he was in his 20’s … and cute.

After dinner, the group migrated to Mr. Gray’s automobile, a Chevy Caprice Classic and a former police car. “You had to start it with a screwdriver because it had been broken into so many times,” he said. “That obviously charmed Laura considerably—I don’t know why.” Then, turning to her: “Maybe it’s because you’re from Arkansas, and it seemed like a piece of home.”

“Yeah,” Ms. Brown said, “I can appreciate a big piece of shit.”

After dropping off their mutual friend, Mr. Gray accompanied Ms. Brown to her hotel, where the two ordered a drink at the bar and wound up making out furiously at his automobile. “Then I sent him on his way,” she said, giggling.

They kept in touch for two years with e-mail, phone and the occasional visit. When the company opened an office in New York, Ms. Brown quickly packed her bags. Mr. Gray had also relocated a year earlier, and the relationship began to bloom in earnest, albeit secretly—each party being eager to avoid the stigma of “office romance.” One night, dining at Ciao Bella in Billyburg, they spotted a pair of colleagues, also on a clandestine date. Everyone successfully averted their eyes.

But after a year of dating, Mr. Gray and Ms. Brown broke up. “We both wanted to figure out where we were in the world,” she said, “and if we were with the right people.”

They stayed friends, though, because that’s the indie-rock thing to do. The night before Mr. Gray left for a six-week vacation in Thailand, they went to a Björk concert and fell for one another all over again. “We were toasted,” Ms. Brown said.

He came to the hospital soon afterward when she had surgery to remove a fibroid tumor. “What’s the story with the two of you?” asked the doctor.

“Well, we’ve always had a very comfortable relationship … ,” Mr. Gray said, stammering a bit.

“It’s time for you to get busy,” said the doc.

“It made me feel like, ‘O.K., it’s time to move forward with life,’” Mr. Gray said.

He had planned to propose on Thanksgiving, but Ms. Brown was in a foul mood after his bossiness in the kitchen ruined her special dish, a green-bean casserole. On Saturday, Mr. Gray woke up early, made her coffee and shaved. “He was acting totally suspicious,” she said.

After Ms. Brown showered, Mr. Gray grabbed her and kissed her. “I love you,” he said, before dropping to one knee and producing a single-carat, platinum-set 1930’s marquis-cut diamond that had belonged to his late maternal grandmother. “Will you marry me?”

Outside, snow was dusting the trees.