Andrew and Zelda have breakfast together and watch Stu as he eats his cereal in an unusual way.
At work, Zelda tries to work with an unusual co-worker, Jennifer, but she believes that her and Stu are a perfect match. Andrew does not believe it is the best idea. Zelda chooses to set Stu and Jennifer up anyway and things go very well. The new couple become very close, very fast. While on a double date, Stephie sees them and is upset that Zelda set Stu up on a date and not her. Stephie begins to feel left out of the new group. Zelda feels guilty about causing Stephie to feel left out and promises to find her a perfect match.
Meanwhile, an ad client for Wallflower, Joseph, visits and Andrew has an idea to set up a profile for him on their site. Lydia wants everything to go perfect with his visit, so she asks Andrew to show him around and finds an opportunity to introduce him to Stephie, who is a match on Wallflower.
At the bar, Andrew and Zelda admire their matchmaking skills for Stu and Stephie. But, across the bar, Stu shows how happy he is for Stephie and Jennifer gets jealous, which causes the end of their relationship. Stu goes into a deep depression after the breakup.
The next morning, Stephie returns from the night out with Joseph where it seems she had a nice time. In actuality, Joseph thought she was a hooker and left money in the room before he left while she was asleep.
Stu is still taking the breakup badly. After a bad day at work, Stephie and Stu disappear and Andrew and Zelda go looking for them. Joseph shows up at Wallflower and Andrew accuses him of paying for sex, but he tells Andrew that he had only left to get breakfast for him and Stephie.
Zelda tries to talk Jennifer into forgiving Stu. Stu and Stephie try to comfort each other over the heartbreaks and end up almost hooking up, until Zelda shows up with Jennifer. The police come to arrest Stephie for stealing money, but the charges are dropped because Joseph explained the confusion. Jennifer breaks up Stu for good. After, Andrew and Zelda feel horrible for their bad match making, but Zelda still promises to set Stephie up until Joseph shows up for another chance and Zelda realizes that Wallflower works.