The Forty Year Old Virgin (2005)

In the middle of Steve Carrell's starring debut, I turned to my wife, sniffled and said "our little Stevie's all grown up."  We'd watched Carrell on the Daily Show for years, (love that show), and to see someone we'd spotted early as a Comer make his big move, and make it successfully in this R-rated raunchy but surprisingly warm-hearted and honest sex comedy was a validation.  No, it's not perfect.  the movie lasts about five minutes too long.  And some of the jokes fall flat.  But he basic predicament, that of a man-boy who finds himself in middle age without ever having carnal knowledge of a woman, and his rather immature friends' attempts to rid him of his burden of virginity, is often a howl.  Carrell is sweet, confused, intelligent, clueless, and entirely fine in a role which might have CKatherine Keener as Trish, the woman he falls in love with. the choice of Keener, (three years older than Carrell) to play a sexy grandmother (dare I say a GILF?) is inspired.  Such a better option than some 25-year old popsy!  I hate to say it, but Andy (Carrell) is damaged goods by my book, virtually a sexual anorexic.  Trish, beginning to believe that she may have run out of good men, feeling she may have passed her sell-by date, is clearly a woman with clear enough eyes to know there is work ahead--and one who could plausibly consider him to be worth the work.  'Cause in general, girls and boys? If someone is a virgin past thirty, your antinnae should tingle like hell.  At any rate, as they say in Hollywood: you'll laugh, you'll cry, you'll kiss eight bucks goodbye.  I give it a B+, and look forward to Carrell's next with happy anticipation.
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SPOILER TIME...
The Hero's journey applied to "Virgin"...

1) Character Confronted with a challenge.  Andy needs to to become a sexual being.
2)  Reject challenge.  He is scared, feels that that aspect of life may have passed him by.
3) Accept Challenge.  Motivated by his friends and a growing sense of frustration, Andy decides to accept a crash campaign to get him laid.
4) Road of trials: a series of dates and dating situations that reveal the flaws in his friends more than those in Andy.  Meeting Trish, and learning how to relate to her and her family.
5) Allies and powers.  His friends, and Trish, and Trish's daughter.  Andy is smart, sweet, and basically a good man with some considerable psychological problems.
6) Confront Evil-defeat.  His 20th-date sexual rendevouz with Trish goes sour as he is overwhelmed with fear.
7) Dark Night.  Not much of one, actually--he almost "settles" for a steamy date with a blonde sexpot, needing to "get over the hump" (so to speak.)  Clearly, he could have taken this option, bu the filmmakers were taking the position that Andy needs his "first time" to be not just a special, but a spiritual experience.  An attitude I'd approve of--if he were nineteen.  At Forty?  Just get it over with, dude.  This is why I cannot write comedy.
8)  Leap of Faith.  He finally tells Trish the truth.
9) Confront Evil--victorious.  Trish and Andy marry.
10) Student becomes the teacher.  Jeeze--did you see the expression on Trish's face on their wedding night? Wow!  They damned near made their case.  Fading out playing "let the sunshine in" from Hair is a bit "on the nose" and weak, but is still funny, and in an odd way, extremely apt and honest.
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And he should have nailed the blonde.