Will Smith is no stranger to the grand romantic gesture. After all, this is a guy who once had a truckload of flowers delivered to wife Jada Pinkett Smith on her birthday. But the A-lister kept things a mite mellower on Feb. 16, when he surprised his spouse of a decade with a belated Valentine's Day celebration. The Vancouver Sun reports he reserved a private wine attic in a local eatery, festooned it with flowers and hired a string quartet to accompany their noshing. Pinkett was said to be "thrilled." No word on whether Will stuck with the theme and presented her with a collection of V.C. Andrews paperbacks.

In related big gesture news, Carrie Underwood didn't need to unwrap her Valentine's Day gift from boyfriend Chace Crawford -- unless he decided to tie a bow around his chest. In Touch says the dreamy-eyed "Gossip Girl" eye candy trekked from Toronto, where he was doing press for the show, to Pennsylvania to surprise the big-haired belter, who is on tour with Keith Urban. An insider says they enjoyed a "romantic night" before Carrie hit the road, with a pal adding, "Chace is really trying to make the relationship work."

Nick Lachey and Vanessa Minnillo at her birthday party in Las Vegas on Nov. 14, 2007

Nick Lachey, meanwhile, opted for a grand but thrifty gesture when it came to marking V-Day with girlfriend Vanessa Minnillo. "I wrote her a song," he tells People. "I put down a demo of it. It's one of those things where [I've] gotten her plenty of things in the past but you want to think a little bit outside the box." Schmoopy crooning aside, the snooze-inducing couple also enjoyed a deluxe dinner Tuesday night in New York, downing Cristal, black truffles and an expensive bottle of red wine at swanky eatery Nello, reports PageSix.com. "They seemed like they were celebrating," says a mole. Perhaps they were just giddy because they weren't responsible for the heartburn-causing $4,700 tab, which was reportedly picked up by one of their deep-pocketed pals. "She and I are a lot alike," the former Mr. Jessica Simpson tells People. "What I've always loved about her is she's just real chill -- we'll go play darts in the bar and have a pint  -- kind of girl. She's low-key and low-maintenance and we just have a good time." Especially, it seems, when someone else is footing the bill.

Miranda Kerr isn't exactly shy about making out in public with Orlando Bloom, but she bobs and weaves when his name comes up in conversation. People mag tried to get the Aussie lingerie model to spill some details about her resurgent romance with the unwisely be-whiskered British actor, who has supposedly been wooing her since April. "He's a sweetheart and that's all I'm gonna say," a "blushing" Kerr told the magazine Wednesday night in New York. "Sweetheart." When asked about their rumored Valentine's Day date, she tap-danced, "I can't tell you. I work for Victoria's Secret -- but that's my secret."

Jason Lewis' appeal to the opposite sex apparently transcends both age and hair color. A seemingly smitten PageSix.com reports that when the tuxedoed, bespectacled and "smokin'" "Sex and the City" stud hit the Costume Designers Guild Awards Tuesday night in Los Angeles, a trio of women scrambled to catch his attention. Lewis, who was recently linked to Jennifer Aniston (they both deny ever having met), reportedly "charmed" a busty blonde, a be-bobbed brunette and a "mature" woman with raven hair.

Derek Jeter may be trying to do some damage control after he was supposedly shot down in a big way last Friday at a Los Angeles hot spot. "Derek was trying to flirt with Sienna Miller," a mole told PageSix.com, "but she didn't know who he was and could have cared less." But the New York Daily News conveniently reports the baseball star's ladies' man reputation rebounded nicely the following evening thanks to a bevy of beauties. "There was a line of women waiting to meet him," a "shocked" eyewitness tells the paper. "He looked like he was really enjoying himself."

Janet and Jermaine Dupri at L.A. Reid's Grammy afterparty in Los Angeles on Feb. 10, 2008

Just days ago, Janet Jackson admitted she "might be allergic to marriage," but that hasn't stopped speculation that she's ready to walk down the aisle, hives or no hives. The New York Post says the twice-divorced singer, who's been coupled up with pocket-size music producer Jermaine Dupri for five years, has been checking out wedding gowns from the likes of Badgley Mischka. "She's preparing for her private nuptials," says an oddly stilted source. Jackson, for her part, finds the nuptial chatter amusing, telling Us, "Let the rumors fly!"

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