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25
The Secret Life of Walter Mitty (2013)
7.3/10on IMDb
Released
Ben Stiller's 2013 version turns a habitual daydreamer's threatened job into a reason to step into the world. The landscapes make an easy shared pleasure; the more interesting question is whether a change of scenery can alter how somebody pays attention. Choose it for an expansive adventure fantasy about ordinary work and aspiration, rather than a practical guide to reinvention.
26
Frances Ha (2013)
7.4/10on IMDb
Released
Frances's friendship, money troubles and uncertain ambitions make adulthood feel like a timetable everybody else received. The nimble black-and-white comedy leaves space to compare what counts as progress when a romantic relationship is not the organising goal. At about 86 minutes it is a compact choice, with strong language and frank sexual talk.
27
Enough Said (2013)
7.0/10on IMDb
Released
Gossip starts to alter a divorced woman's promising relationship before she can separate her own experience from somebody else's complaints. Julia Louis-Dreyfus and James Gandolfini make the attraction specific enough for that problem to matter, in a relaxed comedy about how we decide what counts as evidence.
28
The Big Sick (2017)
7.5/10on IMDb
Released
The early comedy of dating across family expectations gives way to a serious medical crisis, bringing a new partner's parents into an unfinished relationship. The shifts create plenty to discuss about duty, honesty and who gets included in a life. Its warmth is substantial, but a coma and parental conflict make it a heavier two-hour date choice.
29
Begin Again (2014)
7.4/10on IMDb
Released
Recording songs around New York gives two disappointed people a shared project before asking what they want from each other. The creative partnership is the attraction: compare whether the film's most satisfying connection needs to become a romance. The music keeps it inviting, while infidelity, drinking and strong language make the grown-up mess part of the evening.
30
Robot Dreams (2023)
7.6/10on IMDb
Released
A dog buys a robot companion, and their wordless New York friendship becomes a remarkably precise account of connection and separation. You can begin by comparing the visual jokes and musical memories, then talk about whether a relationship must last to remain valuable. Choose it with care on a first date: its warmth comes with considerable heartache.
