Mona and Dee Dee agree to get each other dates as a birthday present. Dee Dee does some thorough research and finds Mona a seemingly perfect guy, James, and the two get along well enough to set up a second date. Mona waits until the last minute to begin her search and is forced to turn to a less-than-helpful Spencer and Adam as she tries desperately to track down someone for her sister. Meanwhile, Dee Dee convinces a reluctant Big Dee Dee to let Mona and Phyllis join them for a mother/daughter portrait sitting. Big Dee Dee and Phyllis see the photograph as another opportunity to outdo each other and go all out to find the flashiest outfits possible.

Mona and Dee Dee attend Neil's wedding, where their conversation with the already-nervous bride in the bathroom leads her to call off the wedding. Mona believes they should stay out of the situation to avoid causing further harm; but Dee Dee insists on taking in the devastated Neil when he shows up on her doorstep. Spencer regrets giving an overly generous tip to the stripper at Neil's bachelor party, and tries to get the woman to return it. Meanwhile, Big Dee Dee fears that she and Phyllis may actually have things in common after they run into each other at a funeral and discover that they both dated the deceased.