Austin Webb is a ladies man with a sensitive (and very silly) side, which is why he invited fans to join him for a Valentine's Day date!

Webb knows the importance of connecting with his fans, especially on social media. That's why he chose to spend his Thursday night (Feb. 11) before the romantic holiday chatting with them on Twitter — while watching the hilarious 1999 flick She's All That.

"I just love talkin' with my fans on Twitter as is and wanted to do something fun for Valentine's Day," the singer explains to Taste of Country. "I'd probably be watching a movie anyway, so I figured why not have a date with my fans?"

"I mean, it's a classic," Webb adds. "You have the all-American stud played by Freddie Prinze Jr. — and Rachael Leigh Cook? She was good lookin' before she got the makeover! And you can't go wrong with any movie Usher makes a cameo appearance in!"

Webb isn't shy about his love for romantic comedies. When he's not watching 'She's All That he may be snuggled up on his couch for 50 First Dates, FeverPitch, Love Actually or the classic tearjerker, Armageddon.