Against all odds, Justin Long is finding himself in a position he never expected to: that of a leading man.

FIRST THINGS FIRST: Justin Long wants you to know that despite his tabloid-splattered year (you may recall the whirlwind romance and abrupt split with a certain A-list actress whose name rhymes with Frew Farrymore), he’s not as cynical as the lay-it-on-the-line character he plays in this month’s He’s Just Not That Into You. “He’s a bit more jaded than I am, and some would say more realistic, in his outlook on women and dating,” Long says.

Long, best known as the Mac guy from Apple’s successful TV ad campaign, has made a career of playing the aw-shucks everyman with geeky tendencies; his films include Galaxy Quest, Accepted, Dodgeball: A True Underdog Story, and Live Free or Die Hard. That persona hasn’t been much of a stretch for the 30-year-old Connecticut native, who says he was “four foot ten and 89 pounds soaking wet” in high school. Never big enough to play football, Long turned to theater once he realized its ratio of girls to boys worked greatly in his favor. “I started acting to meet girls,” Long says, laughing. “And sadly, that remains the reason to this day.”

Not only is Long meeting girls, he’s turned into somewhat of a lady’s man. On-screen, he’s romanced Britney Spears (in the ill-fated Crossroads) and Lindsay Lohan (in Herbie Fully Loaded). He credits his good fortune in part to changing ideals in Hollywood. “Guys like Steve Carell and Seth Rogen have redefined what the leading man really is,” he says. “Only in the movies could someone like me do that well with women.”

Don’t let his modesty fool you: The actor’s been linked to starlets such as Kirsten Dunst in recent months. Still, Long can’t believe his luck. He recalls his and costar Kevin Connolly’s disbelief at working with such a parade of A-list actresses -- Scarlett Johansson, Jennifer Aniston, and Drew Barrymore among them -- in He’s Just Not That Into You. At one point, “Kevin and I just looked at each other and said, ‘What are we doing here? We’re so out of our league,’ ” he remembers.

Though the actor says his character, Alex, comes off a bit pessimistic for most of the movie, the experience of playing him didn’t affect Long’s own approach to romance. “What I learned from Alex is that you just have to take a leap of faith,” he says. “When you’re with somebody, you’ve just got to make the choice to go all in. Sometimes, you get your butt kicked. But you can’t regret it. That’s the nature of love.”

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