S5, E22: After some prodding from (and striking deals with) her Mom, Darlene agrees to go to the prom with David, where she has a surprise deal of her own for her boyfriend. Roger attempts to strike a deal with Dan, using the temptation of being able to make him a ton of money, but is met with a mixed reaction from the Conners. Roseanne attempts a surprise fix-up between Jackie and Roger for a couples' night out, but to Roseanne's surprise, Roger shows up with a date. His choice of date is a jaw-dropping, shock to everyone.