Movies Like How to Lose Friends & Alienate People

If you liked How to Lose Friends & Alienate People (2008), a comedy and romance movie directed by Robert B. Weide, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
The Devil Wears Prada (2006)
★ 7.4/10Also drama and comedy
A young woman from the Midwest gets more than she bargained for when she moves to New York to become a writer and ends up as the assistant to the tyrannical, larger-than-life editor-in-chief of a major fashion magazine.
2
Breakfast at Tiffany's (1961)
★ 7.6/10Also comedy and romance
Holly Golightly is an eccentric New York City playgirl determined to marry a Brazilian millionaire. But when young writer Paul Varjak moves into her apartment building, her past threatens to get in their way.
3
Love Again (2023)
★ 6.7/10Also romance and drama
Mira Ray, dealing with the loss of her fiancé, John, sends a series of romantic texts to his old cell phone number… not realizing the number was reassigned to Rob Burns' new work phone. Rob, a journalist, is captivated…
4
Never Been Kissed (1999)
★ 6.2/10Also romance and comedy
Josie Geller, a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former high school to research contemporary teenage culture. With the help of her brother, Rob, Josie infiltrates the…
5
The Paper (1994)
★ 6.6/10Also comedy and drama
Henry Hackett, a workaholic tabloid editor, has to juggle personal issues, difficult coworkers, a tempting job offer, a looming deadline and a race to land an exclusive on a recent high-profile murder case, all during…
6
It Could Happen to You (1994)
★ 6.7/10Also comedy and drama
Charlie Lang is a simple, kindhearted New York City cop. When he realizes he has no money to tip waitress Yvonne Biasi, Lang offers her half the winnings of his lottery ticket. Amazingly, the ticket happens to be a…
7
One Day (2011)
★ 7.4/10Also drama and romance
After spending the night together on the eve of their college graduation, Dexter and Emma are shown each year on the same date to see where they are in their lives. They are sometimes together, and sometimes not.
8
Bridget Jones's Baby (2016)
★ 6.4/10Also drama and comedy
After breaking up, Bridget Jones' happily-ever-after hasn't quite gone according to plan. Fortysomething and single again, she decides to focus on her job and surround herself with old friends and new. For once…
9
Something from Tiffany's (2022)
★ 6.7/10Also romance and comedy
One woman's life is forever changed by an engagement ring meant for someone else.
10
Maid in Manhattan (2002)
★ 6.1/10Also comedy and drama
Marisa Ventura is a struggling single mom who works at a posh Manhattan hotel and dreams of a better life for her and her young son. One fateful day, hotel guest and senatorial candidate Christopher Marshall meets…
11
Morning Glory (2010)
★ 6.4/10Also drama and comedy
A young and devoted morning television producer is hired as an executive producer on a long-running morning show at a once-prominent but currently failing station in New York City. Eager to keep the show on air, she…
12
Rock of Ages (2012)
★ 6.2/10Also comedy and drama
A small town girl and a city boy meet on the Sunset Strip, while pursuing their Hollywood dreams.
13
The Tender Trap (1955)
★ 6.2/10Also comedy and romance
A young actress flirts demurely with a swinging Manhattan bachelor who thinks he has it made.
14
Picture Perfect (1997)
★ 5.9/10Also romance and comedy
A young advertising executive's life becomes increasingly complicated when, in order to impress her boss, she pretends to be engaged to a man she has just met.
15
Rebel in the Rye (2017)
★ 6.6/10Also drama and romance
The life of celebrated but reclusive author J.D. Salinger, who gained worldwide fame with the publication of his novel The Catcher in the Rye.
16
Just My Luck (2006)
★ 6.2/10Also comedy and romance
Manhattanite Ashley is known to many as the luckiest woman around. After a chance encounter with a down-and-out young man, however, she realizes that she's swapped her fortune for his.
17
The Devil Wears Prada 2 (2026)
★ 7/10Also comedy and drama
Andy Sachs returns to Runway as Miranda Priestly navigates a new media landscape and Runway's position within. The duo reconnect with former assistant Emily Charlton, now the head of a luxury brand that possesses…
18
Sabrina (1954)
★ 7.5/10Also comedy and romance
After two years in Paris, chauffeur's daughter Sabrina returns home elegantly transformed and immediately catches the attention of David, the playboy son of her father's rich employers. David woos and wins Sabrina, who…
19
200 Cigarettes (1999)
★ 5.8/10Also comedy and drama
In 1981 New York City, a collection of twentysomethings try to cope with relationships, loneliness, desire and their individual neuroses on New Years Eve.
20
Confessions of a Shopaholic (2009)
★ 6.5/10Also comedy and romance
In the glamorous world of New York City, Rebecca Bloomwood is a fun-loving girl who is really good at shopping – a little too good, perhaps. She dreams of working for her favorite fashion magazine, but can't quite get…