Winnie has been on a contest kick of late, entering anything no matter what the contest and no matter what the prize. This preoccupation is despite the Gillis family never having won anything before. Winnie is as determined to win something as Herbert is sure that she won't, that they make a bet that if Winnie wins anything, Herbert will allow her to invite her mother and her sister Gladys to come for a six month visit. Technically, their bet is a draw as one of her contest entries does win, but it was contest submitted under Dobie's name, with the prize being a date with famed movie star, Merilee Maribou. The entry was an essay on why he wanted a date with Merilee. Herbert wants Dobie to keep the date so that he can officially win the bet with Winnie, as she can't claim to have written the essay if he does. Dobie, however, has mixed emotions. On the one hand, it is a date with the beautiful and famous Merilee Maribou, who could open doors for him in the entertainment business. On the other hand, going on the somewhat meaningless date could threaten his burgeoning relationship with Jessica Tichborn.
—Huggo