Synopsis for
The 40 Year Old Virgin (2005) Plus avec IMDbPro »

40-year old Andy Stitzer (Steve Carell) has gone his entire life without being with a woman in bed. His friends at the electronics store where he works as an inventory clerk want to correct that situation. They make it their mission to find Andy a woman. They believe it will happen when Andy meets Trish (Catherine Keener), a 40-year old single mother of three, who runs a business across the street from his job. Unfortunately, Andy and Trish begin their relationship with a no-physical contact agreement until after they have had 20 dates. Douglas Young (the-movie-guy)

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.......the title gives you quite a good hint.