01 The gold standard for a proper cry, still working two decades later.
11 Movies to Watch With Your Boyfriend (That He’ll Actually Enjoy Too)
By Vlad Zakh · July 19, 2026
United States Romance falling in love date night
My partner used to groan the second he heard “romance movie” was on the agenda. So over the last couple of years I started paying attention to which ones he’d actually rewatch, not the “chick flick in disguise” picks, but films with a real love story built into a genre he already liked going in.
These are the 11 that made the cut, and why. I’ve organized them by the actual situation you’re in tonight, an early date, a guy who swears he hates rom-coms, a night you both just want to cry, because “what should we watch” almost always really means “what fits the mood we’re in right now.”
A few I’d skip for this specific occasion, from experience: anything off an ex’s favorites list (start your own shared list instead), long subtitled arthouse dramas on a weeknight, and any theatrical cut over three hours when one of you is already watching the clock.
01 
02 Genre chaos plus one of the best portraits of a long marriage ever put on screen.
03 An animated family film with an ability to wreck two grown adults in the same exact moment.
04 Slow, visually gorgeous, and built for conversation afterward rather than during.
05 Restrained, adult, and quietly devastating without ever tipping into melodrama, built for a quiet night in.
06 Storm-chasing and real stakes with a slow-build romance that never stops the action to explain itself.
07 A genuine sci-fi epic where the Paul and Chani relationship is central to the story, not decoration.
08 Tense, competitive, and messier than most rom-coms would dare, with a love triangle built around real tennis stakes.
09 An action movie first, wrapped around a real romance, so it never feels like a bait and switch.
10 A 90s classic that never stops working, short, sharp, and funny even if he's never seen it before.
11 A modern rom-com with real chemistry between the leads, funny and fast-paced enough that there's no dead air on a first or second date.
Frequently asked questions
What's the safest first movie to watch with a new boyfriend?
Anyone But You or 10 Things I Hate About You. Both are funny, fast, low-commitment, and don't require either of you to be emotionally vulnerable on a first or second date.
What if he genuinely hates romance movies?
Pick a film where romance is embedded in a genre he already likes instead of standing alone. The Fall Guy, Challengers, Dune: Part Two, and Twisters all do this well, none of them read as a "romance movie" on the surface.
What's a good movie to make him cry?
The Notebook is still the most reliable choice after 20 years. Coco is the sneakier option if he'd never admit to crying at a romance movie but will absolutely cry at an animated film about family.
Should we pick something we've both already seen or something new?
Depends on your energy that night. New movies are better when you both have the focus to actually watch, not scroll. A rewatch works best on a low-energy night when the comfort of already knowing the story is the point.