I Love You, ManI Love You, Man still manages to stand out when revisiting comedies about waithood from the late '00s, largely because of its unique exploration of male-male friendships. In fact, Paul Rudd stars as Peter Klaven, a fairly successful young real estate agent whose main obstacle in life is his inability to sustain friendships with other dudes. This comes to a head when he gets engaged to Zooey Rice, played by Rashida Jones, and realizes he has no one outside his immediate family to form his wedding party. While it is a comedy about a heteronormative relationship, the primary emphasis of the movie is the burgeoning bromance between Peter and his new best friend, Sydney Fife (Jason Segel). The film uses the framing of the difficulty of forming friendships as an adult to showcase the awkward and sometimes toxic social norms that can exist between men. It also explores the positive aspects of masculinity and homosocial male relationships. I Love You, Man is light and hilarious, but its fantastic portrayal of growing up and male-male friendships allow it to stand the test of time.
Peter barely has time to make friends, but, like a gift from on high, Sydney shows up at an open house he happens to be holding for Lou Ferrigno. The two decide to link up and hit it off over tacos and a shared love of Rush. That said, there are moments of intense awkwardness between the two from the very start. While Peter's inability to come up with a cool nickname like Pistol is awkward, the more uncomfortable part is when Sydney asks Peter about his masturbation habits and sex life. Sydney pressures an initially uncomfortable Peter into sharing. While asking about sex and getting Peter to open up is not toxic, it is the way in which Sydney immediately refuses any boundaries Peter puts up that is so relatable. Sydney also tries to help Peter by relaying the personal info about his relationship with Zooey in a very public way. Sydney also pressures Peter into spending more time with him than Peter is comfortable with and their relationship suffers as a result. Peter thinks his inability to befriend dudes is the problem, but we see that Sydney has trouble with all his friendships, too. Fortunately, the movie ends with a conversation about boundaries and a sweet reunion at the altar between Peter and Sidney. Peter is able to grow and learn how to balance his needs with those of others in a way that is conducive to a strong friendship.
Another side of toxic masculine relationships is shown through Barry (Jon Favreau), husband to Zooey's friend, Denise (Jaine Pressly). Peter tries befriending Barry, but Barry is completely uninterested. We do not get a lot of him, but the moments we do are hilarious. He pressures Peter into a drinking game that Peter wins before puking all over him. He also loses to Peter at poker and reacts by screaming his head off. Barry is the embodiment of a guy with no chill. We do not get to see him when he's in his happy place too often, so as far as the audience is concerned, he is always angry. The kind of guy that always acts like an asshole and does so overtly and irreverently is so common that most men have a friend or acquaintance that reminds them of Barry. While they can be fun to listen to at a dinner party, they can be genuinely exhausting friends. It is great to see Peter eventually not care about becoming friends with Barry.
The film is also not solely critical of men and their standoffishness. Peter's brother and father, Robbie and Oswald (Andy Samberg and J. K. Simmons), present a great example of a healthy relationship between two adult men. They are father and son, but when Peter asks his dad for advice on making friends, his dad tells him that Robbie is his best friend. Peter is able to learn a great deal from Robbie, going to his younger brother for advice on befriending men. Robbie is also gay, so he tries to help Peter from the hilarious angle of determining whether a guy is trying to be friends or more than. This advice does not strictly work and Peter does wind up on a more-than-friend date at one point, and it does introduce a hilarious recurring character who ends up as a groomsman. Still, throughout the film, Peter's friendships with his brother and dad grow, and his dad eventually calls him his best friend.
When Peter eventually figures out how to tell Sydney what boundaries he needs, we know that Peter is ready to navigate the complicated world of adult male friendships. He no longer pines to be one of the dudes at Barry's poker table and has transcended into a guy that is comfortable with himself. It is also framed hilariously, as he and Sydney's friend breakup parallels a romantic one, with Peter telling Sydney he thinks they "should spend some time apart." Also, in true romantic comedy fashion, Sydney rushes into the wedding ceremony mid-ceremony to apologize to Peter, rekindle their friendship, and assume his spot as best man.
While many comedies that center on young men from the '00s can paint them with a broad stroke of misogyny and homophobia, I Love You, Man explores how these characteristics play out in male friendships, and how men can grow past or stay stuck in them. By placing friendships between men as the part of the movie that has conflict and needs resolving, I Love You, Man inverts the friend's usual role as the steady foundation for the leading man while he is going through the wringer in his love life. Throughout the film, Peter and Zooey's relationship is solid, and she is the one who helps Peter get over his breakup with Sydney, and ultimately repair their friendship. I Love You, Man maintains a hilarious absurdity, it manages to position itself as a classic by being a treatise on the sometimes complicated and uncomfortable social norms that exist between men.