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Kat from 10 Things I Hate About You playing the guitar

Choose 10 Of Your Favorite Throwback Songs And We'll Tell You Which '90s Rom-Com You Should Watch Tonight

Pick '90s Songs Get '90s Rom-Com To Watch Quiz

Choose 10 Throwback Songs And We'll Give You An Iconic '90s Rom-Com To Watch

First, pick a song from 1990

1991

1992

1993

1994

1995

1996

1997

1998

And finally, choose a 1999 song

_10 Things I Hate About You_ is a modern-day adaptation of Shakespeare's _The Taming of the Shrew_. The story follows the Stratford sisters, Kat and Bianca, as they navigate high school and romance. Bianca is not allowed to date until her older sister, the feisty Kat, does. A scheming classmate pays another student, Patrick, to court Kat, leading to unexpected feelings and a journey of self-discovery for all involved. This teen romantic comedy explores themes of love, identity, and finding the courage to be true to oneself.

Patrick and Kat from 10 Things I Hate About You leaning in to kiss

"10 Things I Hate About You" (1999)

_Notting Hill_ is a romantic comedy about the unlikely love story between a humble bookshop owner named William and a famous Hollywood actor named Anna. Their paths cross when Anna enters William's small bookstore on Portobello Road in London. Despite their different lifestyles, they embark on a whirlwind romance, facing the challenges of media scrutiny, societal differences, and personal insecurities. This heartwarming film explores the power of love, the pursuit of dreams, and the importance of taking chances on unexpected connections.

Julia Roberts standing in a bookstore while wearing a beret and sunglasses as Anna in Notting Hill

"Notting Hill" (1999)

_You've Got Mail_ is a romantic comedy about two individuals, Kathleen and Joe, who unknowingly become online pen pals while also being rivals in real life. Kathleen is the owner of a small independent bookstore struggling to survive, while Joe is the wealthy owner of a large bookstore chain that threatens Kathleen's business. As they exchange emails and develop a deep connection online, they remain oblivious to each other's true identities. When they eventually discover their offline rivalry, they must grapple with their growing affection for one another and the realization that love can be found in unexpected places.

Tom Hanks leaning in to talk to Meg Ryan as Joe and Kathleen in You've Got Mail

"You've Got Mail" (1998)

_My Best Friend's Wedding_ is a romantic comedy about Julianne, a woman who realizes she's in love with her best friend Michael when he announces his upcoming wedding to someone else. Determined to win him back, she enlists the help of her friend to sabotage the wedding plans. However, as Julianne spends more time with Michael's fiancée and her charming younger brother, she begins to question her motives and the consequences of her actions. This film navigates the complexities of friendship, love, and self-discovery, ultimately teaching Julianne valuable lessons about matters of the heart.

Dermot Mulroney and Julia Roberts smiling at each other as they rub nose's as Michael and Julianne in My Best Friend's Wedding

"My Best Friend's Wedding" (1997)

_The Wedding Singer_ is a romantic comedy set in the 1980s that follows the story of Robbie, a talented singer who entertains guests at weddings. Despite being left at the altar, Robbie still believes in true love. When he meets Julia, a sweet and engaged woman, he becomes smitten. As they spend more time together, Robbie and Julia begin to question their own relationships and realize they may have found true love in each other. Filled with catchy music, hilarious moments, and heartwarming romance, the film explores the power of following one's heart and finding love in unexpected places.

Adam Sandler singing into a microphone as Robbie in The Wedding Singer

"The Wedding Singer" (1998)

_Pretty Woman_ is a beloved romantic comedy that follows the story of Vivian, a charismatic sex worker, who crosses paths with Edward, a wealthy businessman. When Edward hires Vivian to accompany him for a week of social events, they embark on a transformative journey, discovering love and personal growth along the way. This heartwarming film explores themes of overcoming social barriers, relationships based on authenticity, and the power of love to change lives.

Julia Roberts looking at a jewelry box Richard Gere holds open as Vivian and Edward in Pretty Woman

"Pretty Woman" (1990)

This quiz was updated and enhanced using AI-powered creativity tools by one of our editors. Join our community if you want to make a quiz like this!

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Choose 10 Of Your Favorite Throwback Songs And We'll Tell You Which '90s Rom-Com You Should Watch Tonight

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