The 40-Year-Old Virgin

The longer you wait, the harder it gets
The longer you wait, the harder it gets
D: Judd Apatow
Universal (Judd Apatow, Clayton Townsend & Shauna Robertson)
USA 🇺🇸 2005
116 mins (uncut version: 127 mins)
W: Judd Apatow & Steve Carell
DP: Jack Green
Ed: Brent White
Mus: Lyle Workman
Steve Carell (Andy Stitzer), Catherine Keener (Trish Piedmont), Paul Rudd (David), Seth Rogen (Cal), Romany Malco (Jay), Elizabeth Banks (Beth), Leslie Mann (Nicky), Jane Lynch (Paula)
Nowhere near as crass as the title makes it sound, featuring a breakthrough performance from Steve Carell as Andy, a single bachelor with a monotonous stockroom job and an apartment full of comic book collectables, games consoles & tacky 1980's rock posters.
At a work poker night he becomes the butt of his colleague's jokes when they discover he's yet to have slept with a woman at the wrong side of 40.
Together, they take Andy under their wings in a quest to get him laid, offering him advice (some good, some simply awful) to help him get over his fears, but what he really wants more than cheap, tacky sex is a relationship he can connect with.
Like all Judd Apatow's films, the comedy comes mostly from ad-libbed one liners with some funnier than others, but it works especially well here mostly due to the chemistry between the characters. 
Much better than the title might suggest.

Steve Carell in The 40 Year Old Virgin
Steve Carell in The 40 Year Old Virgin