arloGet the appMovies like The 40-Year-Old Virgin
2005 · Movie · R · your starting pointIf The 40-Year-Old Virgin is the itch, these scratch it — some louder, some quieter. Free ones first.
Movies like The 40-Year-Old Virgin, ranked
1. Failure to Launch (2006)
Matthew McConaughey and Steve Carell both stumble through romantic comedies where well-meaning schemes to fix their protagonists' personal lives backfire when authentic connection interrupts the plan.
2. Girl Clock (2009)
Christine's journey toward unexpected life milestones unfolds with the same blend of cringe-comedy and genuine heart that makes watching well-meaning friends meddle in matters of the heart both hilarious and oddly touching.
3. 30 Nights of Sex (2018)
The same awkward-comedy sensibility about real intimacy shines through as misguided well-intentioned schemes spiral into genuine moments of connection and self-discovery.
4. Don Jon (2013)
Joseph Gordon-Levitt directs and stars in this portrait of male sexual confusion, where a protagonist's skewed intimacy expectations finally crack open when genuine connection arrives.
5. No Hard Feelings (2023)
Jennifer Lawrence's deadpan charm navigates the same tender collision between crude humor and genuine emotional growth that made the original so disarming.
6. The Idea of You (2024)
A romantic lead discovering genuine connection despite social pressure and mismatched expectations finds emotional depth in unexpected places, anchored by warm chemistry that transforms initial awkwardness into something genuine.
7. Sex and the Single Girl (1964)
Judd Apatow's protégé directs this 1964 romantic comedy that mines genuine awkwardness from a protagonist's deception, building to heartfelt moments about connection beneath the surface humor and misguided schemes.
Tell me what kind of night it is — I'll pick the one for you.