Kevin Connolly Ditches His Entourage

His new role in He's Just Not That Into You

In the bromance that is HBO's Entourage, cute, one-dimensional girls come and go. So it was with anxiety that Kevin Connolly, best known as the BlackBerry-wielding mogul-in-training "E," took a break from his posse to explore the dreaded "R" word (romance). This month, he hits theaters as hapless-but-hopeful Conor in the self-help manual turned rom-com He's Just Not That Into You.

"Entourage is such a comfortable little fishbowl, so I was a nervous wreck going into this," says 34-year-old Connolly of the film, which finds him entangled with lispy Drew Barrymore and career sexpot Scarlett Johansson. "My first day, I had to kiss Drew, which, while obviously amazing, was still scary" — although not as terrifying as hitting the sheets with ScarJo. "On my first day with Scarlett, we had to get in bed, which seems good on paper, but I couldn't wait for it to be over," he says.

Such boy-next-door prudishness could sound disingenuous coming from the guy who dated Nicky Hilton and figures in the personal entourage of Leo DiCaprio. But with his trust-me blue eyes and gravelly Long Island accent, Connolly makes it easy to believe that nice guys are still lurking out there.

So how does this single, somewhat shy serial monogamist let women know he's interested? "It's tough not to open up with an ice-breaker text," he says. "But I try to make a conscious effort to move to a phone call quickly." Perhaps he picked up that tip from HJNTIY, a book he was "very aware of," thanks to its Bible-like placement on exes' nightstands.

By the end of our chat, when the charming, ruddy actor leaves us with a warm "I'll talk to you soon," we almost believe we'll hear from him. Of course, we've heard that line before.