Winter Watchlist: Feel-Good Romantic Movies on Prime Video
By Shannon Kate Murray, Founder & Editor of High Flying DesignQ4’s here. The leaves are crisp, the lattes are spiced, and my cure for founder fatigue? A good Hallmark-style romance.
Because sometimes the best way to reset isn’t another strategy session - it’s curling up with a cosy film that reminds you why believing in magic still matters. Yes, the acting’s a bit questionable (we’ve all seen worse in amateur dramatics), but these stories do more than entertain. They soothe your nervous system, spark hope, and remind you that slowing down doesn’t mean falling behind.
If you look closely, they’re basically self-growth disguised as rom-coms: the big-city woman re-evaluates her life, rediscovers her roots, and builds success on her own terms. Sound familiar?
Here are four feel-good films on Amazon Prime Video that’ll warm your heart and recharge your motivation this winter.
Sweet Autumn (2020)
A Masterclass in Slowing Down and Trusting the Process
When big-city entrepreneur Maggie inherits half of her aunt’s candy shop (the other half belonging to local maple-farmer Dex), she’s forced to pause, collaborate, and listen - literally through Aunt Dee’s handwritten letters. It’s a gentle reminder that growth doesn’t always mean “go faster.” Sometimes, the sweetest success comes when you stop to taste what you’ve already built.
Available to stream on Amazon Prime Video.
Christmas Pen Pals (2018)
The Power of Stepping Back to See the Bigger Picture
After a breakup and burnout, a tech founder heads home and joins an anonymous pen-pal program. Through simple letters, she reconnects with curiosity, creativity, and what truly matters. A perfect watch if you’ve been glued to your laptop too long - and need proof that reflection can spark more innovation than overthinking ever will.
Available to stream on Amazon Prime Video.
Novel Christmas (2024)
Why Coming Home Can Be the Boldest Move of All
A city-based writer returns to her hometown for the holidays and rediscovers her voice - and her vision - amid small-town simplicity. Sometimes the most “rom-com” thing you can do for your business or your confidence is to reconnect with your roots: what lit you up before the world told you how success should look.
Available to rent or buy on Amazon Prime Video.
Serendipity (2001)
Trust the Unseen Thread
When Sara and Jonathan meet by chance one snowy New York evening, they decide to let fate take over: he writes his number on a $5 bill, she hides hers in a book, and they vow to let serendipity decide. Years later, they’re still haunted by the feeling that something more was meant. A timeless reminder that the best things - in business and in love - often find you when you stop chasing and start trusting.
Available to rent on Amazon Prime Video.
Takeaway Time: Turn Your Watchlist into a Mindset Reset
Curl up, press play, and reflect with these quick-fire prompts:
If your future self could write you a letter, what would it say?
What creative project feels like “coming home” to you?
If your life had a seasonal aesthetic - autumn leaves, fairy lights, handwritten notes - what story would it tell?
Because sometimes the best business plan is a blanket, a rom-com, and a reminder that rest is a growth strategy.
