This month, we’re tackling something new and broaching the topic of—wait for it—date night. Woohoo! I don’t know about you, but my perfect date night is at home with my favorite person, in front of the TV, with our favorite snacks and a good movie or two.
If that sounds like you and your partner or love interest, get comfortable and cozy, then curl up with your person for these three acclaimed rom-coms on Amazon Prime Video.
3
Late Night
Originating from the mind of Mindy Kaling and boasting an 80% Rotten Tomatoes score, Late Night is a fabulous comedy and Oscar nominee about a legendary late-night talk show host. It’s a solid choice to relax and unwind for both you and your date.
After almost 30 years, groundbreaking talk show host Katherine Newbury (Emma Thompson) suspects she’s about to lose her coveted seat on late-night TV after her ratings steadily decline. Her only option is to revamp the show if she doesn’t want the axe, so she swings a game-changing transformation and hires her first and only female writer, Molly Patel, played by Kaling. Though intended to smooth over diversity concerns, Katherine’s decision brings about some unexpectedly hilarious consequences as she and Molly, who are from very different cultures and generations, bond over their love of a biting punchline.
This feel-good dramedy balances its laughs with crucial social commentary and witty writing, for which Kaling is known. She and Thompson give brilliant performances in this timely exploration of workplace diversity, sexism, and finding your voice when it matters. It’s funny, heartwarming, thoughtful, and uplifting, making for a perfect date night flick.
2
Tumbledown
Tumbledown is a sweet little rom-com set in Maine about a widow who falls for her late husband’s biographer. In addition to Jason Sudeikis and Rebecca Hall, Dianna Agron, Joe Manganiello, and Blythe Danner also star.
Hannah (Hall) finds herself a grief-stricken, protective widow after her acclaimed folk singer husband, Hunter Miles, dies suddenly after falling into a ravine. Imagined along the lines of late greats like Nick Drake, Elliot Smith, and Jeff Buckley, Hunter’s music continues to influence listeners, drawing them to his final resting place. When pop culture studies professor and music scholar Andrew McDonnell (Sudeikis) shows up wanting to write about Hunter, it sparks the beginning of a turbulent relationship with Hannah, which soon steadies after she reads his sensitive prose.
You’ll love the strong lead performances in this romantic story that’s much deeper than just fluff. It blends quite a bit of witty humor with poignant explorations of grief, healing, and unexpected love without too much lingering in the painful moments. It offers a sweet look at what it means to move on while also examining the beauty brought about by new beginnings and how both function as modes of healing if you let them.
1
The Big Sick
Based on true events, The Big Sick tells the tale of how a medically induced coma translated into a real-life, epic love story for comedian Kumail Nanjiani and writer Emily V. Gordon. Their cross-cultural romance faced the ultimate test when a medical crisis intervened just as they began to fall in love.
After he meets American graduate student Emily at one of his stand-up shows in the mid-2000s, the Pakistani comic falls hard. As their relationship blossoms, he worries about what his Muslim parents will think of her, but all that changes when Emily suddenly falls ill and is left in a coma. As he waits at her bedside, Kumail develops a deep bond with Emily’s parents, played by Holly Hunter and Ray Romano, and after being diagnosed with a rare systemic autoinflammatory disorder that can shut down major organs if left untreated, Emily wakes up. It had only been eight months, but Kumail was ready to marry her, and he did in 2007.
If that doesn’t give you all the feels and put little hearts and happy tears in your eyes, you’ve got problems. I’m kidding. Seriously though, The Big Sick is refreshingly authentic in a deeply heartfelt take on the rom-com genre. The movie successfully blends humor with serious themes in this true story full of genuine drama and several laugh-out-loud moments.
The Judd Apatow-produced flick received numerous award nominations, including an Oscar nod for Best Original Screenplay. It also won 7 awards, including the Critics’ Choice Award for Best Comedy in 2018.
If date nights with rom-coms are your thing, you can’t go wrong with these recommendations, which are worth your time and any happy tears that may be shed. Remember, guys, that it’s not just the girls who’ll get all misty-eyed. In the immortal words of one Jeffrey Lebowski, “Strong men also cry,” so don’t be afraid to show those emotions. That’s what Date Night is all about! Watch one, two, or all three, but before you do, be sure to level up with overlooked Prime Video features for the best viewing experience possible.
Subscription with ads
Yes, via Prime membership or $9/month
Simultaneous streams
3
Live TV
No
Price
Included with Amazon Prime subscription ($15/month or $139/year) or $9/month standalone
Prime Video has a large volume of content to watch. The other Amazon perks are a bonus as well.

