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The Cast
For the pivotal role of Peter Klaven, Hamburg immediately thought of his longtime friend, actor Paul Rudd. "There's a kind of open-mindedness to this character that I like,” Rudd says. "He has a positive attitude, but is often ill-equipped to handle many situations in the optimal way. He's well meaning, and often wears his heart on his sleeve, but there's something bumbling about him. I relate to Peter, in many ways. John and I keep making jokes that the character is a lot like each of us. For instance, I personally TiVo ‘Antiques Roadshow.' I guarantee that the character I'm playing does too. Unless, of course, his TiVo is filled up with too many (Project) ‘Runways.'”

Rudd has always been a big fan of Hamburg's writing style, he says. "I've known John for years and read many things he's written. All his male characters are similar to him in many ways, and I connect with all of them for the same reason. He's really subtle about writing situations in a very funny but completely guileless way. He truly understands what's funny about the banal.”

Among his favorite scenes in "I Love You, Man,” he continues, are the ones that illustrate Peter's awkwardness around other men as he struggles to fit in. "John's a big fan of uncomfortable pauses and jokes that kind of fall flat. So am I.”

Peter also has a penchant for coming up with what he thinks are cool nicknames that leave everyone scratching their heads. "His phraseology is also a little behind the times – he comes up with strange things that sound like they came out of the mouth of a 14-year-old,” laughs Rudd. "I mean, you don't meet a lot of guys in their 30s who say things like ‘Totes Magotes,' but there's something very funny about being earnest and saying those things. It's so wonderfully dumb.”

Adds producer De Line, "Peter is such a relatable character and Paul brings out an appealing vulnerability that we all share but don't always show. He really walks that fine line and perfectly nails it.”

While holding an open house, Peter chances upon Sydney Fife, a fellow mostly interested in the free noshes who has absolutely no interest in buying a house – and candidly admits it. After his string of unsuccessful – and hilarious – "man-dates,” Sydney is like a breath of fresh air for Peter. He is a bohemian at heart with a casual outlook on life. He lives in a bungalow in Venice and spends his time hanging out with friends, sleeping with various single women and walking his Puggle dog Anwar Sadat (so named for his apparent likeness to the late Egyptian president). A seemingly successful private investor who somehow manages to have all the time in the world for a good hang, Sydney only dates divorcées because of their lack of interest in a committed relationship (and their pent-up sex drive). Unlike Peter, he has a tight group of male friends who provide him with male-on-male emotional intimacy. "Male relationships are the rock of Sydney's life,” comments Hamburg.

To flesh out the enigmatic and charismatic Sydney Fife, Hamburg was certain actor Jason Segel would be Rudd's ideal sparring partner. Hamburg and Segel had worked together several years earlier on Judd Apatow's television series "Undeclared” and Segel has since carved himself a comic niche in films with such hits as "Forgetting Sarah Marshall.”

"I got a call from John, saying that he had this great script and that Paul Rudd was playing one of the leads and he wanted me for the other part,” Segel recalls. "I never get calls like that.”

Segel appreciated the script's naturalistic comedy tone and immediately took to the character. "It's my favorite style of comedy, which is reality-based and not very broad or schtick-y. There are no hacky jokes so, as an actor, you get to bring some naturalism to the comedy.”

The chance to work with Rudd again

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