Met: September 2005

Engaged: Dec. 27, 2006

Projected Wedding Date: June 2008

When Rebecca McFarland first glimpsed dark-haired Charlie Asfour at Crobar in Chelsea, her immediate impression was that—dimples and athletic building notwithstanding—he resembled Eeyore from Winnie the Pooh. “He was very attractive, but very … sad, almost,” Ms. Farland said. “His job was sucking the life out of him.” Mr. Asfour, 24, clocks 120 hours per week as an investment-banking analyst at J.P. Morgan.

They met again one day at Proof, also in Chelsea, where a group of mutual friends was watching the Hoosiers on television. Mr. Asfour is a University of Indiana alumnus and basketball fan, but was too distracted by the petite, brunette, almond-eyed Ms. Farland to pay attention to the game. “I don’t even remember who they were playing,” he said.

“Will you be my steady girl?” he BlackBerried her shortly thereafter.

“I was like, ‘Charlie, you’re being silly,’” said Ms. McFarland, 26, a marketing manager for Vista Research, an information service that supports institutional money managers. “But then the light bulb went off: Maybe he’s interested in me!” she said.

She invited him out to J.G. Melon, near her Upper East Side studio, confessing, “I’m obsessed with cheeseburgers in the city.” (Burp.) After their artery-clogging repast, they headed to Brother Jimmy’s, where Ms. McFarland slammed back a few beers, while Mr. Asfour opted for a Stoli Orange with 7-Up. (“A pretty girly drink for a boy,” the waitress commented.) They played ski ball for two hours before walking back to her apartment, where he deposited her at the door with a chaste kiss before retuning to his own place in Murray Hill.

“From the second we started dating, our friends were like, ‘Oh, it’s obvious,’” Ms. McFarland said, “They were like, ‘You just look so happy and drunk-in-love with each other.’”

But full intoxication didn’t take effect until she attended his father’s 50th birthday party in Chicago, where his mother gave a speech fondly recalling their 30 years of marriage. “I saw myself able to give that speech in 30 years,” Ms. McFarland said. “I just realized: This is the man I’m supposed to marry.”

One summer’s day, Mr. Asfour caught her rummaging through wedding magazines. “Don’t read anything into it!” Ms. McFarland bellowed. “I like reading into it!” he said.

Several months later, he summoned his nerve and secured permission for her hand in marriage from Papa McFarland, a retired two-star general in the Air Force. Speaking of hands, Ms. McFarland kept trying to slip hers into Mr. Asfour’s pockets to keep warm when they took a walk around Millennium Park during another visit to Chi-town (yep, they still have winter there), but he wouldn’t let her. The reason: one was concealing a 2.16-carat, round-brilliant-cut, platinum-set diamond.

Wedding plans have not yet been finalized.