I think it's safe to say Britney Spears like to surround herself with people that has issues. For example, Kevin Federline, Paris Hilton and now she's dating Howie Day (who just left rehab)
Britney Spears met Day while the two were at rehabbing at Promises in Malibu “and fell hard for him”, and that she’s going to bring him as her date when she attends her cousin Erin’s wedding on June 2.
“Britney just lights up and seems back to her old self when she talks to Howie or tells people about him,” “She thinks he’s very talented — and says he’s the best kisser ever!”
But not everyone is thrilled about the romance. Spears’ mother, Lynne, is concerned about Day’s past: he’s been arrested twice and was sent to rehab as part of his probation.
“Lynne wants Britney to be with someone outside the music industry,” says the Spears family insider. “Howie is always on the road and exposed to influences that are discouraged in rehab.”