Valentine’s Day is a time to celebrate connection, companionship, and the joy of a good love story. Whether you’re watching with a partner, a friend, or enjoying a quiet evening at home, a romantic comedy can be a comforting and uplifting way to mark the occasion.

At Flagship Health, we believe shared stories can spark memories, conversation, and moments of connection. Below is a curated list of romantic comedies for seniors to enjoy. These films focus on charm, humor, and heartfelt storytelling, making them easy, enjoyable watches any time of year.

1. Roman Holiday (1953)

Audrey Hepburn stars as a young princess who escapes her royal duties for a day of adventure in Rome, accompanied by an American journalist played by Gregory Peck.

Why it’s a good pick: The film blends romance, humor, and beautiful scenery with a gentle tone that feels elegant and heartfelt.

2. Pillow Talk (1959)

This playful romantic comedy centers on two single professionals who share a telephone party line, unaware they’ve already met in real life.

Why it’s a good pick: Doris Day and Rock Hudson bring warmth and charm, and the movie’s light humor and colorful style make it an easy, feel-good classic.

3. Breakfast at Tiffany’s (1961)

Set in New York City, this beloved romantic comedy-drama follows Holly Golightly, a stylish young woman searching for love and meaning, and the writer who becomes drawn into her world.

Why it’s a good pick: Audrey Hepburn’s iconic performance brings elegance and grace, while the film’s gentle romance, memorable music, and classic setting make it a longtime favorite.

4. Move Over, Darling (1963)

After being declared lost at sea, a woman returns home to find her husband remarried, leading to a series of comedic misunderstandings.

Why it’s a good pick: Doris Day shines in this lively romantic comedy, bringing warmth and energy to a lighthearted story that’s easy to enjoy and fun to rewatch.

5. Barefoot in the Park (1967)

A newlywed couple navigates the ups and downs of married life in a tiny New York apartment, learning how to balance love, independence, and compromise.

Why it’s a good pick: Jane Fonda and Robert Redford bring humor and heart to a relatable story about marriage that feels comforting and familiar.

6. The Goodbye Girl (1977)

A struggling actress and a quirky writer find themselves sharing an apartment—and slowly forming a meaningful connection.

Why it’s a good pick: Richard Dreyfuss’s warm, humorous performance anchors a feel-good story about companionship and second chances.

7. Moonstruck (1987)

Set in an Italian-American neighborhood in Brooklyn, this romantic comedy follows a woman who unexpectedly falls in love while planning her wedding.

Why it’s a good pick: Cher’s Oscar-winning performance and the film’s emphasis on family, tradition, and passion make it funny with plenty of personality.

8. When Harry Met Sally (1989)

This well-loved romantic comedy explores friendship, timing, and love as two people cross paths over several years.

Why it’s a good pick: With plenty of humor and honest moments about love and friendship, the story is an easy and familiar watch.

9. You’ve Got Mail (1998)

Two business rivals unknowingly build a close friendship (and romance) through anonymous emails.

Why it’s a good pick: Tom Hanks and Meg Ryan give this cozy movie a relaxed, comforting feel that makes it enjoyable to settle in and watch.

10. Something’s Gotta Give (2003)

A successful playwright finds herself unexpectedly caught in a love triangle that challenges assumptions about age, romance, and new beginnings.

Why it’s a good pick: Diane Keaton and Jack Nicholson bring authenticity and humor to a story that highlights finding love later in life

A Valentine’s Day Worth Enjoying

The films on this list offer warmth, laughter, and familiar storytelling that make them perfect for a relaxing Valentine’s Day or any cozy evening at home.

At Flagship Health, we believe well-being is supported not only through quality care, but also through moments of joy, comfort, and connection. Taking time to enjoy a favorite movie is a simple way to celebrate relationships and make everyday moments feel special.