Poor Britney Spears doesn’t seem to have an luck in the love department. Britney has been married two times and engaged once after that and now is rumored to be dating someone new. The singer has dated all types of men from different professions and still has no luck. Currently she is rumored to be dating David Lucado, who is a paralegal and bartender. The couple was spotted golfing, going tanning, and more. Often I wonder if Brit regrets cheating on Justin Timberlake when they dated?! See Brit and her man in the gallery.