Alan prepares Walden for a date with Bridget, while Jake decides to emulate Walden and drop out of school.
Guest star JUDY GREER is introduced as Bridget, Walden's ex-wife in the second part of the ninth season premiere.
All is revealed in the ninth season premiere when ASHTON KUTCHER joins the cast as Walden Schmidt, an Internet billionaire with a broken heart.
The multi-talented Ashton Kutcher, whose success spans film, television and social media, joins the cast of the Emmy (R) Award-nominated TWO AND A HALF MEN as Internet billionaire Walden Schmidt in the hit comedy series about men, women, sex, dating, divorce, mothers, single parenthood, surrogate families, money and, most importantly, love.
Rose uncovers Alan's Ponzi scheme and Alan, in turn, meets "Manny," Rose's mannequin "husband." Meanwhile, Charlie is eager to get some alone time with Rose.
In an attempt to grow his business, Alan inadvertently starts a Ponzi scheme using his friends and family as investors. Charlie's love for Rose only deepens as they continue their torrid "affair."
Charlie's obsession with the newly "married" Rose leads him to stalk her. Meanwhile, Alan grows concerned when Jake and Eldridge start videotaping stupid and extremely dangerous stunts.
When Charlie and Lyndsey start becoming friendly, Alan's paranoia gets the best of him.
When Charlie and Courtney break up, Charlie falls into a depression and goes to see his psychiatrist, Dr. Freeman (guest star JANE LYNCH).
Alan is ashamed that he can't afford to buy Lyndsey a birthday present, so he gets creative. JENNY McCARTHY returns as Charlie's girlfriend.
Charlie goes on a spending spree for his old fling, Courtney (guest star JENNY McCARTHY), who shows up after three years in prison for conning him out of money. Guest star CARL REINER returns as Marty, Evelyn's old fling.
When Berta takes a couple of days off, Charlie falls for her replacement (guest star TONITA CASTRO). Meanwhile, Alan believes he's being stalked by Lyndsey's ex-husband. Courtney Thorne-Smith returns as Alan's former girlfriend, Lyndsey and Judd Nelson returns as her ex-husband.
Charlie and Alan try to set up their mother with Russell, the pharmacist (returning guest star MARTIN MULL).
Charlie's past comes back to bite him when his girlfriend (Liz Vassey) decides that his longtime stalker, Rose (guest star MELANIE LYNSKEY), is just too much to handle.
Charlie has trouble adjusting to dating a slightly older woman (guest star LIZ VASSEY - CSI: Crime Scene Investigation).
Alan goes out on the town pretending to be Charlie while Charlie sneaks off for some cosmetic surgery.