Alison Stewart and Bill Wolff didn’t just meet cute. They got to know each other cute before courting cute and, on Nov. 4, marrying cute. Oh, and he got human resources’ blessing before asking her for an actual date that would take their friendship to the proverbial next level. He didn’t propose so cute, but even that seems cute.
Folks who know the brainy and exotically beautiful daytime MSNBC anchor and the quick-witted, unflappable and boy-next-door-ish MSNBC prime-time VP are delighted by it all because to know either one of them is to adore them. To listen to them complete each other’s sentences and stories is alternately charming and alarmingly twins-like.
Their story also is a testament to waiting for Mr. or Ms. Right instead of settling for Mr. or Ms. All Right for Now. This is the first marriage, at age 40, for both.
Mr. Wolff had been at MSNBC about a week, developing “The Situation With Tucker Carlson” when he introduced himself to Ms. Stewart and tried the old “we have a friend in common” line. Clay Tarver, a screenwriter now but a coworker of Ms. Stewart’s at MTV in the ’90s, “is my best friend on Earth,” said Mr. Wolff.
“That’s nice. Have a nice day,” Ms. Stewart replied.
Their second encounter involved “my begging her to be on Tucker’s show and her resisting,” he recalls. “Ultimately it was a fortunate thing she was not interested.”
Because they both lived in downtown Manhattan, he soon was regularly commuting to MSNBC in Secaucus, N.J., with her in her silver 1999 Honda CRV, known as The Alison Express. They got to know each other well.
“We became friends,” they say.
“Then I had a spectacular bust-up with someone,” she said. “The worst ever.”
He proudly answers to The Insider’s characterization of him as Ms. Stewart’s “rebound guy.”
However, she recalls, “I sort of was weirded out. I just broke up with somebody. This really nice, cute guy is paying attention to me. I’ll have drinks with him now and again, but I’m not going to get too serious too soon.”
Then, after a good friend died suddenly at age 41, Ms. Stewart “kind of had that moment of `What are you waiting for? You’re going to stand on ceremony and wait two months because that’s how long you’re supposed to wait?’ That was sort of my epiphany.”
“I’m a great guy. Breaking news,” he says.
Mr. Wolff already had prepared for the prospect of the friendship becoming romantic by revealing to human resources in late summer 2005 that “I’ve kinda got the sweets for an employee here” and being given the green light because Ms. Stewart didn’t work for him.
Still, they kept their relationship under wraps until Oct. 1, when MSNBC colleague Lisa Daniels got married and Mr. Wolff attended as Ms. Stewart’s guest. They set off quite the buzz.
In mid-March, Ms. Stewart booked them a trip to Negril, Jamaica, to warm up after covering the Winter Olympics in Torino.
He had moved into her apartment, bringing with him a very un-Alison-like 50-inch TV, as well as a “lust” for his hometown St. Louis Cardinals. They’d talked about marriage-“for me it was a no-doubter,” he says-and he’d been in possession of an unset diamond for a couple of months, just waiting for the right time to pop the question. As it happened, a “tiff”-neither divulges particulars-proved to be that time.
“It had to do with marriage, as a matter of fact, and I settled the dispute with the diamond,” he says.
Among the 200 or so expected to attend the wedding Saturday were Lisa Loeb (her friend since Brown) actor Donal Logue (his friend since Harvard) and Tucker Carlson (“because it really is his fault,” she says).
The bride chose a strapless, soft-edged champagne satin gown by Judd Waddell, who happened to be at the fabled Kleinfeld’s the day Ms. Stewart tried the dress on and who is from Mr. Wolff’s St. Louis. “It seemed like a natural,” she says. The groom wore a bespoke tux.
As with so much about their relationship, the wedding date “has nice symmetry,” Mr. Wolff says. His birthday is March 4. Hers is July 4. With their anniversary falling on Nov. 4, he says, “every four months we’ll have something to be happy about.”
Somehow The Insider doesn’t think they’ll have to wait that long between bouts of happiness.