Pete Wentz and Ashlee Simpson getting cozy at Debonair Social Club last year. Will Wentz join Simpson during her live performance Thursday at The Underground? Tune in Monday to find out.

Valentine’s Day is sufficiently behind us. In case you were wondering, The Boyfriend did a great job with his surprise plans. We dined at NoMi, at a table overlooking Michigan Avenue. Calling it “romantic” doesn’t even cut it. And my last-minute gift for him: tickets to Citizen Cope, whose music The Boyfriend introduced me to, and who plays the Vic this Saturday. See, even I can be sentimental—sometimes.

Moving forward, there’s no shortage of potential celebrity sightings and events this weekend. When it rains it pours.

In Celeb News:
Ashlee Simpson, younger sis of Jessica and girlfriend of Fall Out Boy’s Pete Wentz, is in town tonight, Thursday the 21st, for a private concert at The Underground. The “private” part runs from 9 to 11 p.m., after which the club opens to the public. Rumor has it, Simpson will stick around for the club’s new weekly DJ series, Treated, featuring DJ Mano. Have a question for Ashlee? Post it in the comment box below, and I’ll try to get her to answer tonight.

Also on the celeb beat: The Grammy-nominated band Wilco, which performed five sold-out Chicago shows this week and last, was spotted at Uptown’s Fat Cat on Friday, Saturday, and Monday nights. When band members showed up following their Monday concert at the nearby Riv, fellow customers gave them a standing O.

In Harry Caray News:
Monday marked the tenth anniversary of the passing of Cubs Hall of Fame announcer Harry Caray. To celebrate the legendary broadcaster, at 7 p.m. tonight in local time zones, thousands of bars in more than 100 countries will participate in the tenth annual Worldwide Toast to Harry Caray. Chicago options include Harry Caray’s Tavern, as well as The Brownstone and Casey Moran’s. Visit the Web site for a full list.

In Nightclub News:
Celebrity (the lounge) is out, and Aberdeen is in at 1856 West North Avenue. The Bucktown/Wicker Park bar plans to open March 8th as yet another restaurant-lounge hybrid—a trend that doesn’t seem to be dying anytime soon—with resident DJs including Jem and Syeyoung.

Coming Up Next Week:
I love it when bars get creative, and Schoolyard Tavern usually has something quirky up its sleeve. This time it’s a “Wedding Party,” Friday the 29th at 7:30 p.m. Wedding cake will be served, and DJs will spin traditional reception fodder; start brushing up on your electric slide now. But the best part (or worst, depending on how you look at it): Come dressed in an old bridesmaid dress, wedding gown, or tuxedo, and you’ll get a free beer. I’m not sure about you, but some of the bridesmaid dresses I’ve worn should earn me an entire keg.


Photograph: Courtesy of Debonair Social Club