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Confessions of a Shopaholic poster

Movies that feel likeConfessions of a Shopaholic (2009)

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 her foot in the door – until ironically, she snags a job as an advice columnist for a financial magazine published by the same company.

If you loved Confessions of a Shopaholic, the closest films we have are My Best Friend's Wedding (1997), Trainwreck (2015) and Set It Up (2018). All three share Confessions of a Shopaholic's witty and playful feel, which is what we rank on before quality.

Seen the big three already? The under-the-radar pick below is Obvious Child (2014).

🍅 26% Rotten Tomatoes★ 5.9 IMDb ↗TMDB ↗dir. P.J. Hoganwittyplayfulromantic
7 of 12 streaming nowNetflix · Disney Plus · Paramount Plus Premium

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If Confessions of a Shopaholic hit the spot, these will too

My Best Friend's Wedding poster
My Best Friend's Wedding
1997 · dir. P.J. Hogan
🍅 75%★ 6.4comedy · romanceParamount+

P.J. Hogan working the same nerve twice

The difference: Reviewed even better

When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Michael -- and sets out to sabotage the wedding.

Trainwreck poster
Trainwreck
2015 · dir. Judd Apatow
🍅 84%★ 6.2comedy · romance

Both keep coming back to the same thing: romcom

Ever since her father drilled into her head that monogamy isn't realistic, magazine writer Amy has made promiscuity her credo. As much as she enjoys an uninhibited life free of commitment, Amy is really in a rut. While writing a profile about charming and successful sports doctor Aaron Conners, she finds herself actually falling in love for the first time -- and what's more, Aaron seems to really like her too. Amy starts to wonder if it's time to clean up her act and face her fears.

Set It Up poster
Set It Up
2018 · dir. Claire Scanlon
🍅 92%★ 6.5romance · comedyNetflix

Both rooted in New York City

Two overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.

Obvious Child poster
Obvious Child
2014 · dir. Gillian Robespierre
🍅 90%★ 6.7comedy · romance

Witty where it counts, playful underneath

An immature, newly unemployed comic must navigate the murky waters of adulthood after her fling with a graduate student results in an unplanned pregnancy.

Zack and Miri Make a Porno poster
Zack and Miri Make a Porno
2008 · dir. Kevin Smith
🍅 65%★ 6.5comedy · romance

Comedy built on romance, twice over

Lifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each other than they previously thought.

To All the Boys: P.S. I Still Love You poster
To All the Boys: P.S. I Still Love You
2020 · dir. Michael Fimognari
🍅 78%★ 6.1romance · comedyNetflix

Romance with a pulse of wit, in both cases

Lara Jean and Peter have just taken their romance from pretend to officially real when another recipient of one of her love letters enters the picture.

What's Your Number? poster
What's Your Number?
2011 · dir. Mark Mylod
🍅 23%★ 6.1comedy · romanceNetflix

The same preoccupation in both: romcom

Ally Darling is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96 percent of women who've been with 20 or more lovers are unlikely to find a husband. Determined to turn her life around and prove the article wrong, Ally embarks on a mission to find the perfect mate from among her numerous ex-boyfriends.

How to Be Single poster
How to Be Single
2016 · dir. Christian Ditter
🍅 45%★ 6.1comedy · romance

Playful comedy in both cases

New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.

Valentine's Day poster
Valentine's Day
2010 · dir. Garry Marshall
🍅 18%★ 5.8comedy · romance

Romantic romance, and it commits to that

Intertwining couples and singles in Los Angeles break-up and make-up based on the pressures and expectations of Valentine's Day.

I Now Pronounce You Chuck & Larry poster
I Now Pronounce You Chuck & Larry
2007 · dir. Dennis Dugan
🍅 15%★ 5.9comedy · romanceStarz

Both lean on wit more than on comedy

Firefighters Chuck Ford and Larry Valentine are guy's guys, loyal to the core—which is why when widower Larry asks Chuck to pose as his lover so that he can get domestic partner benefits for his kids, his buddy agrees. However, things get dicey when a bureaucrat comes calling, and the boys are forced to present a picture of domestic bliss.

What Happens in Vegas poster
What Happens in Vegas
2008 · dir. Tom Vaughan
🍅 25%★ 6.1comedy · romance

Playful romance, and it commits to that

During a wild vacation in Las Vegas, career woman Joy McNally and playboy Jack Fuller come to the sober realization that they have married each other after a night of drunken abandon. They are then compelled, for legal reasons, to live life as a couple for a limited period of time. At stake is a large amount of money.

27 Dresses poster
27 Dresses
2008 · dir. Anne Fletcher
🍅 41%★ 6.2comedy · romanceDisney+Starz

Both work the same romance

Altruistic Jane finds herself facing her worst nightmare as her younger sister announces her engagement to the man Jane secretly adores.

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The best-reviewed films that share Confessions of a Shopaholic’s defining feeling.