3x18 "The One with the Hypnosis Tape"

A desperate Monica agrees to a date with one of her restaurant customers, who turns out to be very well off (Pete, played by Jon Favreau). Phoebe freaks when she finds out that her 18-year-old brother is planning to wed a woman more than twice his age (Debra Jo Rupp). Chandler uses a hypnosis tape to quit smoking, but it is meant for women, which causes Chandler to act feminine.