The 10 best movies like ‘How to Lose a Guy in 10 Days’

Nostalgia is in and in a big way, especially when it comes to romantic comedies of yesteryear like How to Lose a Guy in 10 Days. While it feels like we’re on the precipice of a rom-com renaissance with a recent surge of films like Do Revenge and Choose Love trying to capture that feeling for a new generation of viewers, it’s hard to top the rom-coms of the ‘90s and 2000s.

Something about “chick flicks” — and I’m using that here as a term of endearment — of the era just hits differently. Give us a stylish protagonist who’s working in publishing (seriously, why is every rom-com heroine a journalist?) and a love interest she just can’t seem to get out of her head and we’re golden. Here’s 10 movies like How to Lose a Guy in 10 Days to watch next time you’re craving a classic rom-com.

13 Going on 30 (2004)

This rom-com also serves as a cautionary tale; who knew getting everything you wanted when you were a teenager could result in really having nothing at all? The comedy comes from newly 13-year-old Jenna waking up in her 30-year-old body after a birthday wish gone awry while the romance comes from Jenna realizing her best friend may have been the one for her all along.

The Proposal (2009)

In reality, this film would be a workplace harassment lawsuit waiting to happen but as a film, it’s a sweet movie about Ryan Reynolds falling in love with his uptight Canadian boss Sandra Bullock as they plan to commit marriage fraud. Not ideal in reality, but fun in fiction!

10 Things I Hate About You (1999)

If you like Shakespeare (or even if you don’t), this movie is for you! Similar to How to Lose a Guy in 10 Days, this film follows a romance formed out of a bet and like that film, is a classic rom-com albeit one set in high school. Shakespeare wishes.

Legally Blonde (2001)

If you love seeing ambitious women succeed in their career and their love life, look no further than Legally Blonde. Watch Elle Woods achieve her law school dreams and look great in pink the whole time. “What, like it’s hard?”

The Holiday (2006)

One of my personal favorite comfort films, The Holiday follows two women (Kate Winslet and Cameron Diaz) who decide to swap homes during the holiday season to get a break from their respective exes. They not only get a nice vacation out of the deal; they also find love with Jack Black and Jude Law along the way. Watch this if you like a good cozy rom-com.

Bridget Jones Diary (2004)

Many a good romantic comedy reinterprets a literary classic for the modern age and Bridget Jones Diary is one such film. An adaptation of Jane Austen’s Pride and Prejudice, Bridget Jones Diary follows the titular heroine as she starts keeping her eponymous diary and writes of the life she wants to live. Funnily enough, most viewers will want her life after watching Colin Firth and Hugh Grant fight over her in the snow. That’s cinema, baby.

Princess Diaries 2 (2004)

Hear me out: I love the first film as much as anyone does but Chris Pine is in this. Can you blame me?? I love Chris Pine, I love Anne Hathaway, and I also love a great enemies-to-lovers plot; I would also love a third film starring the two but alas, I can’t have everything.

Crazy, Stupid, Love. (2011)

Is this film perfect? No. Does it have to be? No. Is Ryan Gosling in it? Yes. Honestly, that would be enough to get me to watch it but Crazy, Stupid, Love. also has an excellent ensemble cast and a lot of silly but cute moments which makes it one great watch.

When Harry Met Sally (1989)

When Harry Met Sally is a quintessential romantic comedy about two college acquaintances who keep turning up in each other’s lives years after graduation. Their relationship is mostly a “will they, won’t they” situation for most of the film, but the resulting romance is worth the wait. Bonus points for all the cozy sweaters in this film; they really don’t make ’em like that anymore.

The Devil Wears Prada (2006)

This isn’t really a romantic film (we hate Nate in this household), but The Devil Wears Prada is 100% chick flick through and through. I watch this film when I want to experience a great story with some great fashion and have a few laughs along the way. What more could you ask for in a film?