Valentine’s Day is around the corner. Everyone’s thinking about romance and candy that tastes like chalk. As you find something to snack on you’ll probably want a movie to watch too. Here’s my list of 27 films to watch during this lovely time.

1. Love & Basketball (2000)

A classic hoops and hearts movie for any age. Monica and Quincy go from childhood sweethearts to adults with an on again, off again, relationship. The audience is left hoping that home court points will be scored before it’s too late.

2. About a Boy (2002)

This film is perfect for anyone who loves British stories. Will is a mentor to a kid named Marcus, and Marcus helps Will connect with a single mother.

3. Little Manhattan (2005)

Two kids go to elementary school together in Manhattan, allowing the audience to remember a simpler time. Back when relationships were based on karate kicks and exploring local parks.

4. The Photograph (2019)

Two millennials start a relationship as the woman, Mae looks into her mother’s past. The guy, Michael find himself interested too, as he covers a story for work that intertwines with Mae’s world. Will the past repeat itself? Or will the next generation keep a good thing going? This film moves well between NYC and New Orleans, the present, and the past. It’s a beautiful film for a calm night.

5. Crazy Rich Asians (2018)

Rachel’s life is flipped upside down when she finds out her boyfriend Nick is actually from a rich family in Singapore. There’s trouble in paradise though, as she now has to win over his mother.

6. Nick & Norah’s Infinite Playlist (2008)

If you were an alternative kid in high school this one’s for you.

7. She’s All That (1999)

One superficial bet changes two teenagers lives forever. Well, at least until the end of high school. This film screams late 90’s, and inspired most of the plot of Not Another Teen Movie (2001), so it’s a must watch.

8. Poetic Justice (1993)

Your postal clerk isn’t Tupac, but you wish he was. This film features a small road trip via postal van. So this movie is definitely for anyone who likes quirky moments that are part of a serious love story.

9. Spiderman (2002)

We all know about the kiss by this point, and we will never get tired of it. The rest of the story is good too.

10. Ghost (1990)

If you want to do ceramics after this movie just say dido.

11. Clueless (1995)

You’re totally buggin’ if you don’t want to follow the lives of some kids in Beverly Hills.

12. American Pie (1999).….and the many sequels and spin offs.

I would recommend serving cake during this showing. Just to keep things a little classy.

13. Say Anything (1989)

Size matters. A boom box is much better than a phone or an iPod.

14. Lucas (1986)

One teens quest to win over the girl, and just about everyone else as well. It’s the 80’s so spoiler warning, that epic slow clap.

15. Fever Pitch (2005)

Ben needs to hit a homerun with his new girlfriend Lindsey, but he’s more focused on Red Sox games. I’m a Yankees fan myself, but this movie is great regardless of who you root for.

16. The Love Birds (2020)

We follow the main characters Jibran and Leilani through an extremely quirky love story. This film is a funny adventure with well delivered over the top moments.

17. Love, Guaranteed (2020)

While this film is a little dry at times the plot is extremely modern. Nick is dissatisfied with a dating site so he wants to sue them. This is how he meets Susan, and while feelings are there, everyone’s avoiding the elephant in the room. In an era where human interaction is less common it’s nice to remember how important a physical presence is. As I write this list we are still in a pandemic, so please don’t misunderstand me. Once the pandemic is over we can all go out more. For now stay safe and wear a mask.

18. Juwanna Mann (2002)

In this love triangle, or possibly a love quartet, we see Jamal fall for Michelle. The problem is that Michelle only knows Jamal as Juwanna. This movie is a hilarious mix of basketball, second chances, and love.

19. Career Opportunities (1991)

Who knew Target could be so romantic?

20. Aaron Loves Angela (1975)

Two teenagers fall in love in New York City. The kids have to deal with prejudice, parents, and some dangerous characters.

21. Always Be My Maybe (2019)

Sasha and Marcus were childhood friends, but now that they’re adults they might want something more. This film is an adorable boy next door, girl next door story.

22. East Side Sushi (2014)

Juana starts a new job at a sushi restaurant where she meets Aki. Juana deals with being an outsider in the sushi world, and the feelings she and Aki are developing for each other.

23. What Dreams May Come (1998)

The main character Chris really goes through fire and back for his wife Annie.

24. When Harry Met Sally (1989)

It’s a classic, and almost everyone has seen it at least once, but it never gets old.

25. Continental Divide (1981)

A journalist falls in love. It’s much better than how I just described it.

26. Grease (1978)

A high school love story with great musical numbers.

27. Sleepless in Seattle (1993)

Another classic everyone has seen, but can always watch again.

I’ll end my list here, even though I could definitely keep going. Let me know if you watch any of these during the Valentine’s Day season. Which movies would you add to the list?