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Chiropractor and single father Alan Harper lives in a beachfront house with divorced Internet billionaire Walden Schmidt, who bought the house following the untimely death of Alan's brother, Charlie. As they acclimate to their living arrangement, the tightly wound Alan finds himself taking on a mentor role with Walden, whose lifelong dependence on being taken care of has left him a bit naive. Despite his unsuccessful romantic history, Alan also tries to help Walden overcome his limited experiences with dating. Berta, a sharp-tongued, unapologetic housekeeper, is also featured in the series.
S5, EP2 "Media Room Slash Dungeon"
Charlie behaves strangely after an evening with his mother; Alan's date (Janeane Garofalo) reacts oddly after making love.
S2, EP19 "A Low, Guttural Tongue-Flapping Noise"
Alan asks one of Charlie's beautiful ex-girlfriends (Jeri Ryan) on a date, but while they are out he is tormented by thoughts of her with Charlie.
S5, EP3 "Dum Diddy Dum Diddy Doo"
Charlie lets Alan set him up with a woman his own age.
S2, EP20 "I Always Wanted a Shaved Monkey"
When Charlie and Alan take their personal frustrations out on each other, Rose tries to help the brothers sort out their feelings.