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Two And A Half Men Season 5 Episode 18 - If My Hole Could Talk
Charlie seeks relationship advice and finds himself attracted to an older self-help author (Susan Blakely); Alan’s insistence that Jake complete his The Taming of the Shrew book report is hampered by Jake’s continually losing the book.
Title quotation from: Charlie, to Angie, after she says he may have a “hole” in him.
Air Date: 12 May 2008