When: 2003
The two were first introduced when Spears visited the set of Farrell's S.W.A.T.. After they were spotted making out at L.A.'s Troubadour nightclub, it was rumored that they were dating. At the time, Farrell was said to be dating Demi Moore and Spears had recently broken up with Limp Bisket's Fred Durst. Days later, the two showed up hand in hand to the Hollywood premiere of The Recruit and were reportedly spotted making out. Smashing a pop princess is always a win, but going after Fred Durst is always an L.
Smash Probability: