1. “Wedding Crashers” (2005) – Rated R

Have you dreamed of crashing a wedding? Hopefully not, but this amazing rom-com gives you all the thrill you need and even an unexpected romance. Jeremy Grey (Vince Vaughn, “IF”) and John Beckwith (Owen Wilson, “Cars”) make a living as divorce mediators. When they are not at work, they spend their time crashing wedding receptions. After finding out about a high-profile event, Grey and Beckwith know that it will be the ultimate crash if they are able to pull it off. The only flaw in their plan? Beckwith falls hopelessly in love with bridesmaid Claire (Rachel McAdams, “Mean Girls”). Will Grey get jealous of or mad with Beckwith? Will the duo’s wedding crashing antics cease? Find out by watching “Wedding Crashers” on HBO Max!

2. “How to Lose a Guy in 10 Days” (2003) – Rated PG-13

Interested in some dramatic irony? Look no further than “How to Lose a Guy in 10 Days!” Andie Anderson (Kate Hudson, “Song Sung Blue”) is an advice columnist writing her next big article on how to get a man to leave you in 10 days. Needing a guy to experiment on, she finds Ben Berry (Matthew McConaughey, “Interstellar”) who, unbeknownst to her, is on his own mission: have a woman fall in love with him in only 10 days. If you would like to see where this ends, “How to Lose a Guy in 10 Days” is currently streaming on Peacock and Paramount+.

3. “My Big Fat Greek Wedding” (2002) – Rated PG

Do you sometimes feel unsure of where your life is headed and feel like everyone else has their things in order? Worry not, you are not falling behind; everyone goes at their own pace! And to remind you of that, try watching “My Big Fat Greek Wedding.” Full of hysterical moments, this rom-com follows Toula Portokalos (Nia Vardalos, “My Life in Ruins”), a 30-year-old unmarried woman who still works in her parents’ restaurant. Shortly after she gets a job at her aunt’s travel agency when the restaurant is not enough, Portokalos finds love in Ian Miller (John Corbett, “To All the Boys I’ve Loved Before”), a teacher who is not Greek. With a sequel just as charming, this film is definitely worth the watch. You can find this rom-com on HBO Max.

4. “The Princess Bride” (1987) – Rated PG

While it is debated on whether “The Princess Bride” is a rom-com, elements of the genre are sprinkled throughout, making it a worthy contender. The fantasy and family themes only add to the storybook love of Buttercup (Robin Wright, “Forrest Gump”) and Westley (Cary Elwes, “Robin Hood: Men in Tights”). The plot, characters and comedy make this a notable cult classic. “The Princess Bride” can be found on Disney+.

5. “When Harry Met Sally…” (1989) – Rated R

If you have seen “When Harry Met Sally…” then it might be no surprise why it is on this list. Besides the unmatched on-screen chemistry between Meg Ryan (“Sleepless in Seattle”) and Billy Crystal (“Monsters, Inc.”), the film features many iconic scenes, a very memorable monologue and a realness that does not come through in all rom-coms. Even though “When Harry Met Sally…” is great on the first watch, you should absolutely run it a second time to get everything you missed originally. Side note, tissues are recommended. You can watch for free with ads on YouTube or Hulu.