Movies Like 'How to Lose a Guy in 10 Days'

Updated on October 16, 2019
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Rahul is a movie addict who can never get enough of good films. His all time favorites are Inception, 12 Angry Men, and Scarface.

What Movies Are Like How To Lose A Guy in 10 Days?

Ah, romantic comedies! They're often called cliched, sappy, and idealistic in portraying the concept of love. Love them or hate them, they're here to stay. As the idea of romance gets complicated, these movies act as a warm throwback to simpler times. Out of tons of films in this genre, How To Lose A Guy in 10 Days prominently stands out.

Featuring Kate Hudson as Andie and Matthew McConaughey as Ben, this film is a rom-com lover's paradise. Both Andie and Ben start seeing each other with a hidden agenda of their own. Hilarity ensues as they try their best to outmaneuver each other. The other one just won't let them!

With such a promising set up, it's hard not to be drawn towards this film. If you loved this directorial work by Donald Petrie and are looking for similar films like How to Lose A Guy in 10 Days, I have got you covered. Take a look at some of the best romcoms Hollywood has to offer.

Movies Similar to How to Lose A Guy in 10 Days

  1. Sex And The City
  2. The Wedding Planner
  3. Sweet Home Alabama
  4. Monster-In-Law
  5. Just Like Heaven
  6. Fool's Gold
  7. 27 Dresses
  8. The Proposal
  9. He's Just Not That Into You
  10. Never Been Kissed

1. Sex And The City

Following the lives of four New Yorkers—Carrie, Miranda, Samantha, and Charlotte— this 2008 movie adaptation of the famous HBO sitcom is admired by many. Set a few years after the series, the main plot revolves around Carrie and her new boyfriend, Big. In order to get a better apartment in NYC, Big proposes to marry Carrie, to which she readily agrees. However, chaos in the love lives of her three friends ruins her wedding and she's left stranded right at the altar.

With four powerhouse actresses carrying the film, you'll get sucked into their messy lives right away. One of the major takeaways the film is the power of friendship. Each one has individual struggles, but with love and support from each other, they weather these storms with ease.

In spite of being a romantic comedy on the surface, Sex And The City is an empowering movie - a transfixing story encouraging women to be independent and not rush into things they aren't ready for.

2. The Wedding Planner

Starring Jennifer Lopez and Matthew McConaughey, The Wedding Planner is your run-of-the-mill drama, with some funny situations thrown in between. Lopez plays a wedding planner who meets Ben, played by Matthew, by accident. The two go on an impromptu date and hit it off, but soon part ways due to other commitments. In order to really make a mark in her career, Mary (Lopez) decides to plan her boss' wedding.

Things, however, don't go as smooth. Little does she know that she's about to get the shock of her life. Things get murkier for our protagonist as she's torn between her career and finding love. What will she choose?

Both the lead actors have done a fabulous job, carrying the whole affair with grace. Since Matthew had established himself as the chocolate boy back in the late 90s, this role probably was a cakewalk for him.

The ridiculous situations they find themselves in will leave you conflicted. While a part of you will find it partially relatable, another part will find this Adam Shankman directional outlandish.

3. Sweet Home Alabama

Sweet Home Alabama portrays unconditional love and the pain of loss with unflinching poignance. However, it's not a grim affair.

Reese Witherspoon plays Melanie, a simple small town girl from Alabama, who makes it big in New York as a fashion designer. After getting engaged to one of the most promising bachelors in town, she's forced to confront her troubled past. It turns out that Melanie has a husband back in Alabama who won't divorce her.

In order to get hitched to the big city hotshot, she goes back to her town to convince her husband to let her go. However, as she finds herself in familiar surroundings, she realizes that life in the idyllic small town wasn't so bad after all.

Reese Witherspoon is a phenomenal actress and she proves her mettle yet again with Sweet Home Alabama. Ever since its release in 2002, the film has gained a lot of recognition over the years, with many considering it to be a rom-com staple.

If you're looking for some movies like How To Lose a Guy in 10 Days, Sweet Home Alabama will not disappoint you.

4. Monster-In-Law

They say marriages not only brings two people together but it conjoins their families as well. After watching a romp like Monster-In-Law, above line makes more sense, in an ironic way.

This comic caper follows the lives of Charlotte and Dr. Kevin Fields. After the two hit it off really well, Kevin pops the big question. Charlotte accepts and is really excited about their big wedding. Little does she know that her life is about to be turned upside down as she comes face to face with Kevin's mother Viola, aka monster-in-law, played by Jane Fonda.

After losing her job as a news anchor, Viola is in a vulnerable position. She is protective of her son. As you can imagine, the jealous mother gives Charlotte a really hard time as she tries her best to break off the nuptials. Even as you feel bad for Charlotte, you can't help but chuckle at their hilarious catfights.

Jane Fonda is the star of the show, pulling off a difficult role like this with panache. While she gets most of the camera time, rest of the cast has done an incredible job as well.

5. Just Like Heaven

If you're looking for a rom-com with some spook factor, this should fit your bill. Featuring Mark Ruffalo and Reese Witherspoon, Just Like Heaven is a sweet love story, with a supernatural twist.

Ruffalo plays David, who moves into a new apartment in San Francisco. This is no ordinary apartment, as it's haunted by a woman's ghost named Elizabeth, played by Witherspoon. A terrified David initially tries to get rid of this unwelcome guest, but Elizabeth is convinced she isn't dead and refuses to leave.

The desperate man tries everything, including hiring a medium to communicate with her, but to no avail. Strangely, over time, he warms up to the spirit and falls for her. I know it's super weird and cheesy, but you'll love this refreshing and welcome spin on the rom-com genre.

6. Fool's Gold

Ben, a treasure hunter, is a workaholic. His marriage with wife, Tess, as a result, is falling apart. Money, however, will heal all the scars, at least that's what Ben believes

When Ben uncovers the whereabouts of a legendary treasure called Queen's Dowry, he immediately ropes in his wife and her boss, billionaire businessman Nigel Honeycutt, in this quest. However, things are not so cut and dry. There's fierce competition for Ben and his little team in form of Moe Fitch, former mentor turned rival.

Rest of the tale is about these two groups fighting with one another to win the gold for themselves. Fool's Gold dabbles more with adventurous themes than most rom-coms. There's some action involved with the leads finding themselves in precarious situations.

At times, it feels as if its romance and comedy aspects are mutually exclusive from each other. One thing is certain; by the end of the film, you will be cheering and rooting for Ben to not just find the treasure but to fix his marriage as well.

Fool's Gold is a perfect admixture of romance and action - an anomaly in a market crammed with brain-dead movies. If you're looking for a film like How to Lose A Guy in 10 Days, this Andy Tennant directed feature should be right up your alley.

7. 27 Dresses

27 Dresses may seem like an innocent, sweet, comedy on the surface, but it does ask some tough questions about the idea of putting everyone else before yourself.

This Anne Fletcher directional stars Katherine Heigl as Jane, a peculiar woman who's addicted to weddings. Thanks to her perpetual excitement to attend weddings, she often finds herself playing bridesmaid to random people.

However, her whole world turns upside when her younger sister decides to get hitched. Jane is secretly in love with the groom. Will she confess her feelings towards him? Will she come clean to her sister about her suppressed feelings?

Since it's a comedy, you can rest assured that she won't learn her lessons before making some bad decisions. This fun ride delivers a profound message - one that'll make you think.

8. The Proposal

Faking a wedding to avoid deportation is not the best of ideas. Not that I have ever contemplated it, but if any of you have ever pondered pulling something preposterous like that, let this capricious flick change your mind.

The Proposal stars Sandra Bullock and Ryan Gosling as Margaret and Andrew respectively. Andrew is Margaret's assistant. Since Margaret's Canadian, she encounters a major problem with her work visa and faces deportation. This is where all the trouble begins.

In order to avoid being deported, she coerces Andrew to marry her, with the promise that he'll be made editor if he follows through. He reluctantly agrees and as they spend time with Andrew's family in Alaska, a genuine romance sparks between them. Not without a fair share of drama, of course.

Sandra and Ryan have both played their parts extremely well. Sandra's manipulative character will definitely get a rise out of you, especially in the beginning. One can't help but feel bad for Andrew, the assistant. Other than the two leads, supporting characters have done an amazing job as well.

As ridiculous as the film's plot may be, it manages to keep audiences hooked.

9. He's Just Not That Into You

Directed by Ken Kwapis, this film is an amalgamation of several stories. The plot follows the lives of five women and four men as they venture into the uncharted territories of the dating world. Will they figure it out?

Some tales here have a happy ending while others do not. Featuring a stellar cast with some of the biggest actresses in Hollywood, the film can be called an anthology. Well, not exactly, as the lives of each of these women are somehow connected, if only by a single thread.

The critics complained that in spite of a great cast, no story was given enough screen time. Hence, the characters were reduced to stereotypes. While the critics gave this rom-com the cold shoulder, the box office figures told a completely different story. This Ken Kwapis directional was a stellar hit among the masses. If you're not very nitpicky, this flick is for you.

10. Never Been Kissed

High school drama and teenage angst are perfect ingredients for rom-coms. Starring Drew Barrymore, Never Been Kissed caters to all the stereotypes one can associate with high schools. You've got the jocks, the popular kids, and of course, the nerds.

Drew plays a reporter for a magazine - a teenager dealing with low self-esteem, thanks to her hellish years in high school. Her past comes back to haunt her when her editor sends her undercover as a high school student. Mortified and dejected, she reluctantly braces herself to face her inner demons. Although challenging, she learns a lot about herself through this ordeal and also finds love - something she desperately craved in her life.

Drew is not afraid to make a fool of herself in front of the camera. Some of it is painful to watch, but it'll also leave you howling with laughter. It's hard not to relate and sympathize with her character.

Did I miss out on any other good movies like How to Lose A Guy in 10 Days? Let me know in the comments section. I'll be happy to update the list if your suggestions tick all the boxes.

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