Valentine’s Day Fun (and Dramatic) Movie Recommendations for True Romance Fans

Cheery (and Touching) Romance Movies for Valentine’s Day

Valentine’s Day is typically a very romantic time of the year, and people try hard to find the perfect film to capture the essence of the day. The following films all fit the bill as romantically appealing movies that serve to help define what the holiday is about.

Say Anything

This teen romance film was directed by Cameron Crowe and showcased John Cusack and Ione Skye in memorable performances as high schoolers, Lloyd Dobler and Diane Court, who are almost ready to move on to the real world as the film begins. They find comfort in one another’s company as they slowly get to know one another. John Mahoney portrays Diane’s dad who holds a secret that will make Diane’s life that much harder as she goes off to college. She will need Lloyd more than ever now even though she doesn’t initially realize it.

This is the famous 1989 movie where Cusack’s Lloyd held up the infamous boom box to try to win back Skye’s character’s affections after a break in their relationship. The song, “In Your Eyes,” plays as Diane is in bed pondering her true feelings and dealing with her difficult dilemmas. The beauty of Crowe’s film is that it never sugarcoats the romance and makes it ultra-realistic which makes almost every scene in it ring true. It’s the perfect drama for Valentine’s Day as it is so memorable and touching with Cusack and Skye earning the audience’s appreciation with their delicate and sensitive on-screen work.

13 Going on 30

Jennifer Garner never had more fun on-screen than she did playing Jenna Rink in the 2004 comedy, 13 Going on 30. This movie is a story where a young teenager wakes up to be a 30-year-old woman (Garner) working in publishing. She tries to find her sweetheart from her school days, Matty (played by Mark Ruffalo as an adult), and when she locates him, she does everything possible to try to make their connection a romantic one even though he is potentially going to be partnered with another woman in his adult life. Garner dances to Michael Jackson’s “Thriller” with an entourage in the most humorous scene in the picture and Ruffalo’s Matty is right by her side. This is a beautifully fun and entertaining movie that has the bright and colorful Valentine’s Day spirit embedded in it. It’s the female version of Big.

The MatchMaker

Janeane Garofalo plays Marcy Tizard in the little Irish gem from director Mark Joffe that was released in 1997, The MatchMaker. Marcy arrives in a village where a matchmaking festival is going on in order to find her boss (a Senator)’s distant relatives. Marcy meets a nice guy with a big heart, Sean (David O’Hara), and starts to learn that she may be vulnerable to falling in love, herself, despite her skeptical personality. This movie is super entertaining and beautiful to watch with its extravagantly pleasing Ireland locations, and it is emotionally uplifting with the aging local matchmaker (Milo O’Shea) adding some sensitivity and humanity to the mix. With its sweet music and touching ending, The MatchMaker is quite likely to appeal to fans of the romance genre many times over.

The Bridges of Madison County

Clint Eastwood’s The Bridges of Madison County may be one of the most moving dramatic love stories ever made. Robert Kincaid (Eastwood) is the National Geographic photographer who arrives in a small town and meets Francesca Johnson (Meryl Streep), a married housewife whose life will never be the same as she gets to know the earnest Kincaid. Eastwood is in top form with a performance that is emotionally vulnerable. This film features a sequence where Kincaid is standing in the rain as Francesca is alone in her husband’s car waiting for the husband’s return. Kincaid knows he will love Francesca forever and the moving film keeps the intensity of the romance intact as important choices are made that will break hearts forever. This film’s ending has the power to make an audience cry and is quite affecting. Ashes are spread at the conclusion as characters leave this Earth, but love has never seemed more alive than in this movie.

Laggies

Keira Knightley plays Megan in the 2014 charmer from the late, great director Lynn Shelton, Laggies. Chloë Grace Moretz portrays a young teenage girl, Annika, who asks the older Megan to help her out and, surprisingly, the two form an unlikely bond as Megan escapes her demanding friends and her fiancée in order to live away from everybody in Moretz’s character’s dad’s house. There, Megan meets Annika’s father, Craig (Sam Rockwell, always terrific) who is a good parent to Annika. Craig asks a lot of questions such as why the 20-something Megan is associating with his teenage daughter. Soon, the separated Craig and Megan are drinking together and having a good time getting to know one another. Could Megan leave her engagement to stay with the new family she is forming with Craig and Annika? Laggies is a blast that keeps the entertainment light and sweet and is the perfect subtle Valentine’s Day gift for comedy fans. Rockwell and Knightley create memorable chemistry that will truly win audiences over.

What’s Your Number?

Sometimes, it is important to highlight a movie that seemed to have gotten lost in the shuffle with mediocre box-office results and reviews. What’s Your Number? from 2011 is, quite simply, a blast from beginning to end. It’s a romantic comedy that stars the very likable Anna Faris as Ally Darling who realizes she has slept with nearly 20 men and wonders if one of them wasn’t the “one” who got away. Her personable and good-looking neighbor, Colin (Chris Evans), has the perfect personality to match Ally’s witty nature, but the two won’t know it for most of the movie. One scene has the pair playing a strip basketball game together that is absolutely delightful. While Bridesmaids got all the attention that year this film came out (and is a perfectly great film itself), What’s Your Number? was also a sweet, humorous gem that has just enough funny scenes and its fair share of heart to win over fans of romance, especially this time of year.

There are other fine romance films such as Titanic, Jerry Maguire and La La Land, but those won Oscars and have been widely seen and talked about. I hope one of the movies I’ve mentioned can help someone discover a new favorite romantic gem. These movies have appealed to me greatly over the years and are sure-fire remedies to warm your heart as cupid shoots his arrows today.

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