15 Romantic Comedies to Binge on a Winter Day
It’s the season of chilly winds and snugly blankets, a perfect time to unwind with a glass of your favorite wine. And what’s a better way to complement the rich flavors of a Sterling Vineyards selection than with a heartwarming romantic comedy? Whether you're wooing someone special or relishing some 'me-time', this curated list of rom-coms is bound to enhance your winter evening and tickle your taste buds.

Winter is the perfect time to cuddle up on the couch with a blanket and watch a movie. While classic films know no season, winter seems particularly evocative of the romantic comedy. These films are often set against the backdrop of snowfall, twinkling lights, and the coziness that this season is known for. So, pour yourself a glass of Sterling Vineyards' finest, and let's dive into the feel-good world of romantic comedies. Here are 15 movies that will not only make you laugh, cry, and believe in love but will also perfectly pair with the notes of your chosen wine.
1. "The Notebook"
No wine-list is complete without a shoutout to "The Notebook," and for good reason. This tale of enduring passion deserves a wine that's equally timeless and rich. Our oaky Reserve Chardonnay would be an excellent choice.
2. "You’ve Got Mail"
Sip on the smooth and delightful Reserve Mount Veeder Cabernet Sauvignon while watching this quintessential email-era love story set in New York City. The wine’s sophisticated taste profile parallels the journey of the film's characters.
3. "The Holiday"
When two women swap homes for the holidays and find love, it's an enchanting tale that goes perfectly with a glass of Reserve Red Wine Blend— a wine as balanced as the film's narrative.
4. "When Harry Met Sally"
A classic exploration of friendship and love, this film navigates the complexities of the heart with humor and candor. Sally's feisty personality and Harry's world-weary wisdom pair well with a robust red, such as our Reserve Calistoga Cabernet Sauvignon, complementing the film's deep conversations and bold characters.
5. "Pretty Woman"
A modern-day fairy tale set in the heart of bustling Los Angeles, "Pretty Woman" is the perfect mix of romance and charisma. To match the luxurious ambiance of the film, opt for a smooth and sophisticated blend like the Winemaker's Select Red Blend.
6. "Love Actually"
As the name suggests, love in all its varied forms takes center stage in this mosaic of relationships. To mark the film's British setting, you might enjoy sipping a glass of Unoaked Chardonnay, capturing the essence of a London winter day.
7. "How to Lose a Guy in 10 Days"
The cat-and-mouse game of love in this film needs a wine that's equally calculated and winning. A glass of bubbly California Brut will keep the mood light and fresh, much like the story itself.
8. "Hitch"
This urban rom-com calls for a wine that's as suave and confident as its matchmaker protagonist. A powerful and structured Reserve Yountville Cabernet Sauvignon will be your perfect wingman for the evening.
9. "The Proposal"
This trans-continental romp features the tumultuous love story of a strict boss and her assistant. The film's mix of humor and heart pairs wonderfully with a lighter, more refreshing white wine, such as our Winemaker's Select White Blend.
10. "Crazy, Stupid, Love"
The film’s duality between crazy and sensible relationships is a perfect match for a complex but balanced Pinot Noir. When sipping on our Reserve Russian River Pinot Noir, you'll find it deepens the narrative of love's twists and turns.
11. "Bridget Jones’s Diary"
Embark on Bridget's journey of self-discovery with a glass of Rosé of Syrah, capturing her charmingly clumsy misadventures and quests for love. Its light-hearted notes echo the film's comedic and hopeful tone.
12. "Notting Hill"
Romance blooms amidst the curious backdrop of suburban London life. The film's blend of idyllic and everyday charm is encapsulated by the rich Iridium Cabernet Sauvignon— the perfect choice to elevate your viewing experience.
13. "10 Things I Hate About You"
A modern retelling of Shakespearean romance set in high school, this film's mix of drama and humor calls for a wine that's young, fresh, and spirited like the characters. A glass of Malvasia Bianca-Muscat Canelli is right on cue.
14. "Sleepless in Seattle"
This poignant narrative of love found across the vastness of the U.S. beckons for a wine that's both inherently American and deeply satisfying. Choose our Platinum Cabernet Sauvignon for its robust yet approachable taste.
15. "27 Dresses"
Finally, the story of a woman who's been a bridesmaid 27 times offers a multitude of wedding pairings. But given its light-hearted tone and comedic notes, the Oak Knoll Pinot Gris would be a delightful companion to this film's palette.