We’re all familiar with the story of the struggling writer who gives up his morals in order to make it big in the competitive real world. In How to Lose Friends & Alienate People, Simon Pegg (Shaun of the Dead, Hot Fuzz) plays a fish-out-of-water British journalist who is thrust into the cutthroat world of celebrity pop journalism in New York City. This romantic comedy is based on Toby Young’s best-selling book about his experience working at Vanity Fair.

Dreaming of living the glamorous life since he was a little boy, Sidney Young (Pegg) catches the attention of Sharps magazine editor-in-chief Clayton Harding (played by a long-haired Jeff Bridges) by crashing a black tie event; soon thereafter he’s flown to the Big Apple to write for the magazine. Sidney is instantly wrapped up in a life of VIP parties and swanky celebrity-studded get-togethers. However, he never quite blends in with the Hollywood elite. From hiring a transvestite stripper on “Take Your Daughter to Work Day” to killing an ingénue’s beloved dog, Sidney is the likeable idiot who can’t seem to do anything right — except draw a few good laughs from the audience.

In the midst of his quirky antics and immature pranks, Sidney manages to charm his co-worker Alison (Kirsten Dunst). An aspiring novelist, Allison dreams of moving beyond snapping photos at the most recent celebrity gathering. Sidney’s main struggle throughout the movie is the classic big-screen journalist dilemma: deciding between writing puff pieces for the magazine — a duty he truly despises — or writing the meaningful, truthful articles he desperately wants to produce.

Sidney meets Sophie Maes (played by Megan Fox from Transformers), a shallow red-carpet starlet, and is instantly determined to sleep with her. Before he knows it, he is drawn into the cultish celebrity world of mindless superficiality. After leaving his subversive behavior behind and giving into the game that his high-powered publicist (Gillian Anderson) wants him to play, Sidney begins to see the rewards: instant fame, a fancy apartment, a prominent position at Sharps and a budding relationship with Sophie.

While the initial concept of How to Lose Friends is appealing, it leaves the viewer with a lot of loose ends — it seems as if too much is being squeezed into the film’s 110-minute running time, and certain characters are not explained in enough detail. The distance of Sidney’s relationship with his father, for example, is never adequately accounted for; we’re left wondering why their relationship was strained and if it ever recovered.

Furthermore, the movie doesn’t delve deep enough into the sleazy side of celebrity journalism. It only touches on this when Sidney is forced to write a flattering portrayal of a clueless up-and-coming young director — it could have taken a stronger stand. Even the ending seems rushed and unsatisfying.

The movie, however, does have some redeeming aspects: Think The Devil Wears Prada with a male lead and raunchier jokes. Jeff Bridges owns his role as the magazine chief nostalgic for his former days working at a more independent, less prominent publication. Meanwhile, Pegg has excellent comic timing and proves adept at pulling funny faces.

While it’s easy to root for the small-time Brit trying to make it big in the dog-eat-dog world of celebrity journalism, we all know better. In reality, having a good heart and trying to do the right thing won’t necessarily get you that top position with a shiny new Rolex. How to Lose Friends & Alienate People valiently tries to be a warm and enjoyable movie packed with an abundance of laugh-out-loud jokes, but when it comes to combining witty humor with a heartfelt message, this misfire comedy falls short.