Movies Like The Proposal: My 2026 Rom-Com Watchlist

Hey, fellow rom-com lover! I rewatched The Proposal again last night — yes, in 2026, and yes, I still laughed at the office banter, the Alaska chaos, and the fake engagement that turns into something real. The 2009 movie stars Sandra Bullock as Margaret Tate, a high-powered book editor who pretends to be engaged to her assistant, Andrew Paxton (Ryan Reynolds), to avoid deportation to Canada. Their trip to Alaska to meet his family is packed with awkward dinners, family secrets, and a slow-burn romance that makes the enemies-to-lovers trope feel fresh. If you love that mix of witty dialogue, workplace tension, and fake-dating magic, you are in the right place. I have gathered the best movies like The Proposal for your next cozy marathon. 🍿❤️

Why The Proposal Still Works for Me

• Enemies-to-lovers done right: Margaret and Andrew start as boss and assistant, not soulmates. Their insults are sharp, but their growing respect feels earned.

• Fake dating chaos: The immigration interview, the family reunion, the naked collision — every set piece uses the fake relationship for comedy.

• Workplace romance: The power dynamic is messy, but the movie leans into the complications instead of ignoring them.

• A believable change of heart: Andrew wants a promotion; Margaret wants to stay in the country. By the end, they want each other. That transition is the rom-com gold.

• Great supporting cast: Betty White, Mary Steenburgen, and Craig T. Nelson add warmth and laughs.

10 Rom-Coms to Watch After The Proposal

1. 27 Dresses (2008) — This one follows Jane, a perpetual bridesmaid who has secretly loved her boss for years. When her sister gets engaged to him, Jane has to plan the wedding while watching her own love life crumble. Like The Proposal, it mixes wedding chaos, personal sacrifice, and romantic misunderstandings. Katherine Heigl is charming, and the movie understands that putting yourself first can be the hardest romantic choice. 💐

2. The Wedding Planner (2001) — Jennifer Lopez plays Mary, a wedding planner whose life is turned upside down when she falls for a doctor who turns out to be the groom in her biggest wedding yet. The workplace romance, the professional complications, and the unexpected love triangle all echo The Proposal. It is a delightful mix of career ambition and romantic chaos. 💒

3. Just Friends (2005) — Ryan Reynolds stars as Chris, a former overweight teen who returns to his hometown as a successful music executive. He tries to win over his high school crush, Jamie, but old habits and new embarrassments get in the way. The movie uses unrequited love and personal transformation for big laughs, and it has one of Reynolds' best comedic roles. It is slapstick, but it also has real heart. 🎶

4. Sweet Home Alabama (2002) — Reese Witherspoon plays Melanie, a New York fashion designer who has to go back to Alabama to finalize a divorce from her childhood sweetheart before she can marry her wealthy New York fiancé. The film explores identity, belonging, and second chances. If you liked the Alaska family dynamics in The Proposal, you will love the Southern charm and small-town warmth here. 🌾

5. How to Lose a Guy in 10 Days (2003) — Kate Hudson and Matthew McConaughey are perfectly matched in this battle-of-the-sexes rom-com. Andie writes an article about driving a man away; Ben bets he can make a woman fall in love with him. Neither knows the other's game. Like The Proposal, it runs on deceit, chemistry, and the moment when pretend feelings become real. 💘

6. The Ugly Truth (2009) — Abby is a romantically challenged morning show producer, and Mike is her chauvinistic correspondent. They clash over love, sex, and relationships, but their professional partnership starts to blur into something more. The enemies-to-lovers energy is strong, and the humor is edgier than most 2000s rom-coms. It is a great pick if you want sharp banter with your romance. 🎤

7. Leap Year (2010) — Anna travels to Ireland to propose to her boyfriend on Leap Day, but bad weather and a grumpy innkeeper named Declan derail her plan. The two bicker across the Irish countryside until they inevitably fall for each other. The picturesque journey and playful chemistry make this one of the most heartwarming The Proposal alternatives. 🍀

8. Two Weeks Notice (2002) — Sandra Bullock returns to rom-com territory as Lucy, an idealistic lawyer who works for George, a charming but selfish billionaire played by Hugh Grant. When she quits, both realize their feelings too late. The workplace romance, witty banter, and antagonism-to-affection arc make it a natural follow-up to The Proposal. ⚖️

9. Just Go With It (2011) — Adam Sandler plays Danny, a plastic surgeon who asks his office manager, Katherine (Jennifer Aniston), to pose as his soon-to-be-divorced wife. The lie snowballs into a Hawaiian vacation full of comedy and unexpected romance. The fake-relationship trope is used for maximum laughs, but the Aniston-Sandler chemistry gives it genuine sweetness. 🏝️

10. You've Got Mail (1998) — Tom Hanks and Meg Ryan play rival bookstore owners who despise each other in real life but fall in love online. This classic rom-com uses the enemies-to-lovers formula with wit and charm. It is older than The Proposal, but it shares the same belief: two people who seem wrong for each other can become exactly right. 💌

Quick 2026 Rom-Com Cheat Sheet

So there you have it — my personal watchlist for anyone who still swoons over The Proposal. In 2026, these movies are easy to find on major streaming platforms, and they pair perfectly with a blanket, snacks, and a phone on silent. Whether you want the wedding chaos of 27 Dresses, the Irish adventure of Leap Year, or the online romance of You've Got Mail, there is a fake-engagement, enemies-to-lovers, or workplace-romance story here for you. Tell me: which one are you watching first? 💕