Everybody has that one friend who can’t help but complain about everything: the eternal pessimist. You tell them you got a dog and they’ll say that it’s going to die one day. You’re getting married, but they remind you that divorce rates have never been higher. It’s pervasive, and the second you catch yourself thinking like that friend you get the sudden, uncontrollable urge to hurl yourself through a plate glass window.

“Brad’s Status” is that friend. But instead of launching yourself through that window, you have to sit through the director/writer Mike White’s one hour and 41-minute collaboration with Ben Stiller because you agreed to review movies for your school’s newspaper. It’s an age-old dilemma.

Stiller stars as the titular Brad Sloan, a 47-year-old, middle-class Sacramentan touring colleges in the Boston area with his musically-gifted 17-year-old son, Troy, played admirably by Austin Abrams. Despite having his own nonprofit, a content marriage with his grounded wife (Jenna Fischer), and a son primed to go to Harvard, Brad’s life is plagued by insecurity, which typically manifests itself in the form of obsessive envy over his four mega-successful college friends.

“Brad’s Status” sets up a lot of pins, asking serious questions about some of the more nagging parts of human nature, like why we always compare ourselves to our friends or why we struggle to appreciate how much we have, but it never knocks them down and gives any concrete solutions. Instead, Brad’s inner monologue feels dragging and invasive, like you took a wrong turn on your way to the theater and accidentally walked in on this joyless shell of a man giving his therapist the play-by-play on his mid-life crisis.

That’s not to say “Brad’s Status” is a complete failure with nothing to hang its hat on: Stiller pulls off his character with remarkable nuance and tact. In one scene, Brad is walking the streets of Cambridge alone, and you can see his eyes trailing off and watching younger, happier-looking people pass him on the sidewalk. For an actor who built his career on over-the-top caricatures like Derek Zoolander and the “you can trouble me for a warm glass of shut the hell up” guy from “Happy Gilmore,” Stiller makes a three-dimensional human being out of Brad. Considering Stiller is far closer in terms of social stature to the college friends that Brad is so envious, it’s a pretty impressive achievement.

The only problem is, three-dimensional or not, Brad isn’t a particularly likeable protagonist. He worries about pointless hypotheticals like his son’s potential success as a musician making himself feel worse about his own stagnating professional life and pictures himself on the beach making out with two women in the Harvard orchestra. For a movie where the central conflict takes place in the main character’s head, the audience has to like or identify with the character, or else the whole experience turns into an uncomfortable one-on-one lunch with that one friend.

Somewhere near the end, the movie tries to suggest some type of answer to the legitimate question of social comparison bias. Brad learns that his friends have issues that challenge the image he has of them in his head. Despite their wealth or fame, they’re victims to the worse human pitfalls than Brad, which is unsatisfying because it only confirms that anyone, if they work hard enough, can achieve crippling despair too.

“Brad’s Status” conveys plenty of troubling insight to the way people work, but it just never quite makes it all the way to that light at the end of the tunnel.