10 Comfort Rom-Coms We Can Rewatch Forever

When Harry Met Sally (1989)

This beloved classic offers a charming take on how friendship can slowly turn into love. Harry and Sally first meet after graduating from the same university and share a ride to New York, where they debate whether men and women can truly remain just friends. Over the years, they keep crossing paths while navigating relationships, heartbreak, and adulthood. As they grow closer, their friendship becomes increasingly complicated by feelings they can no longer ignore.

Crazy Rich Asians (2018)

An evergreen rom-com that never loses its charm. The story follows Nick Young and his Chinese-American girlfriend, Rachel Chu, as they travel to Singapore for a wedding and for Rachel to meet Nick’s family. She soon discovers that Nick belongs to one of the wealthiest families in the country. Their relationship faces tension when Nick’s mother, Eleanor, disapproves of Rachel and considers her unsuitable for Nick.

How To Lose a Guy in 10 Days (2003)

This classic rom-com stars Kate Hudson as Andie Anderson, a magazine writer working on an article about how to drive a man away in ten days. At the same time, Matthew McConaughey’s Benjamin Barry makes a bet that he can make any woman fall in love with him within the same period. When Andie and Ben start dating, both secretly use the relationship to achieve their own goals. However, things become complicated when genuine feelings begin to develop between them.

Crazy Stupid Love (2011)

This heartfelt rom-com follows Cal, a middle-aged man going through a midlife crisis after his wife, Emily, asks for a divorce following an affair. At a bar, he meets Jacob, a smooth bachelor who helps him reinvent himself and regain confidence. While Cal struggles to embrace Jacob’s carefree lifestyle, Jacob unexpectedly falls hard for Hannah, a woman who changes his perspective on love and relationships. The film beautifully weaves together multiple love stories filled with humour, heartbreak, and second chances.

To All The Boys I’ve Loved Before (2018)

This charming teen rom-com became an instant internet favourite after its release. Based on Jenny Han’s bestselling novel, the story follows Lara Jean, whose secret love letters accidentally get mailed to all her past crushes. To avoid embarrassment and make his ex-girlfriend jealous, Peter Kavinsky agrees to fake date her. What starts as a pretend relationship slowly turns into something much more genuine as their chemistry deepens.

Palm Springs (2020)

This quirky rom-com adds a fun sci-fi twist to the genre through a time-loop storyline. Nyles is stuck reliving the same wedding day over and over when he meets Sarah, another guest who gets pulled into the loop alongside him. As the two embrace the chaos and freedom of repeating the same day endlessly, their bond grows stronger. Beneath the humour and absurdity, the film delivers a surprisingly heartfelt love story about growth, connection, and choosing happiness.

Always Be My Maybe (2019)

This heartfelt rom-com follows childhood best friends Sasha and Marcus, whose teenage romance ends after a painful fight drives them apart. Sixteen years later, they reconnect when Sasha returns to San Francisco as a successful celebrity chef, while Marcus continues living a quieter life close to home. As they spend more time together, old feelings begin to resurface along with unresolved misunderstandings from the past.

27 Dresses (2008)

A comforting rom-com built around weddings, bridesmaids, and second chances. Jane Nichols has been a bridesmaid 27 times and has always dedicated herself to helping others find their happy ending. However, her own love life becomes messy when her younger sister, Tess, falls for Jane’s longtime crush and boss, George. As Jane struggles with heartbreak and betrayal, she meets Kevin, a cynical writer who sees beyond her people-pleasing nature and encourages her to finally put herself first.

What’s Your Number (2011)

Can your dating history really determine your chances of finding love? Ally Darling, a 30-year-old woman living in Boston, begins to panic after reading an article claiming that women with too many past relationships are less likely to find a husband. Determined not to increase her number, she reconnects with her exes to see if one of them could be “the one.” Along the way, her charming neighbour Colin helps her with the search, and their unexpected connection slowly turns romantic.

Set It Up (2018)

This wholesome rom-com follows two overworked assistants, Harper and Charlie, who are desperate to reclaim their personal lives from their demanding bosses. Hoping to make their jobs easier, they come up with a plan to set their bosses up romantically. Surprisingly, their matchmaking scheme works, but as Harper and Charlie spend more time together planning elaborate meet-cutes, they begin to question their own relationships and discover feelings for each other.