Steven Wakefield has it bad. He's "in love" with this girl named Jill Hale. Though he took her out on a date, things went so bad that now she barely speaks to him. Janet Howell starts picking on him, even though it wasn't that long ago that she was obsessed with him, and points out that Jill is now dating her older brother Joe. Jessica makes a bet with her that Steven can get over Jill in the next week. If she wins, she and Elizabeth get Janet's tickets to some random show called Staying Up with Bob or something like that, but if Janet wins, she gets Liz's new camera.
Liz is, naturally, unhappy with this agreement but agrees to help her twin win the bet. Since the only girl Steven ever spends time with is his friend Cathy Connors, they decide that she's his perfect match. They make plans to send her a bunch of gifts from a secret admirer, which will then make Steven so jealous that he falls in love with her.
They first decide to send her a dozen roses, but the cost is way out of their budget, so they send her tulips. The lady running the flower shop loves their secret admirer story so much that she even sends her more flowers than they can afford. Caroline Pierce conveniently sees the delivery truck and brings it up in front of Steven. Unfortunately, Steven doesn't really care because he's still obsessed with Jill.
This leads him to make a fool of himself in front of her. He accidentally spills chocolate milk all over her and keeps saying the wrong thing. When she reveals that she likes motorcycles, he lies and says he's about to buy one. She gushes over him a little but still makes it clear that she's all about the Joe.
Steven buys a motorcycle magazine and realizes that owning a bike costs money. Since he only has 30 bucks in savings, he needs to get a part time job. Ned and Alice are less than thrilled because apparently he's too busy with basketball and band, but they agree to let him apply. He runs around town and keeps whining about how he wants a real job before asking Cathy to get him a job at the mall restaurant where he works.
Jessica and Elizabeth need more money to buy Cathy gifts, but their parents won't give them any advances because their grandmother gave them $100 each not too long ago. Steven offers them $1.50 if they do his laundry for him. Jessica ends up finding his savings and rushes off to spend it. Liz catches her, she refuses to say where the money came from, and they have a huge fight. Liz refuses to help her until she tells her where the money came from.
They do get a bunch of heart shaped balloons and leave them outside Cathy's house. Each time they leave her a gift, they leave her a selection of letters too. Steven and Cathy start goofing around at work, they make a huge mess, and Jill shows up. She acts really cold around him, but Cathy convinces him to ask her out. He does, and Jill just laughs it off.
Steven finally goes to Joe and tells him he's in love with his friend's girlfriend. Joe thinks it's funny because he actually doesn't like her that much. It turns out that she only wants what she can't have and that she's one of those girls who does whatever a guy wants. Joe wants a girlfriend who has her own interests. Also, Jill only liked motorcycles because Joe and his dad bought one they plan on fixing up together.
The next time he goes to work, he and Cathy goof around until he realizes that he actually likes her. They wind up kissing just as the twins show up with one last gift. Cathy puts the letters together and realize it spells Steven Wakefield. They kiss again, and the twins snap a picture of them together.
Believe it or not, Steven doesn't mind. He and Cathy both get fired for goofing around on the job, and he tells Ned and Alice the whole story. Every one is fine up until the twins mention the bet. The Wakefields decide that it isn't right for them to take an expensive item from Janet. Steven offers to give them the money to buy the tickets from her.
Elizabeth shows up at a Unicorn Club meeting with a picture of Steven and Cathy kissing. Janet grumbles but agrees they won and hands over the tickets. Jess repeats everything their parents told them about betting getting out of hand and how they shouldn't bet expensive things. Janet agrees to save face and decides to sell them the tickets and change the way club members can bet in the future.
The television show has some stupid tricks segment, and Liz becomes obsessed with somehow getting on the segment. She tries a bunch of stuff like wiggling her ears and balancing a ping pong ball on her nose before stumbling across a stupid trick by accident. Steven tosses a pea at her, which she hits with a knife and sends it right into the middle of his forehead. It turns out that she can do it every time.
She and Jess go on the show and sit at a ping pong table made up like a dinner table. She keeps hitting Jess in the head with peas as the crowd goes wild until she catches the last one in her mouth. People at school go crazy and greet them with flower bouquets. It's kind of a big deal.
*Steven gets insulted when he can't get a job at a computer store and the guy calls him unskilled. Dude, you're a freshman, of course you're unskilled.
*He also applies for a job as a lifeguard and gets pissed off when he can't get a job without passing certification first. Everyone keeps telling him to apply at a fast food place, which ticks him off because those jobs suck.
*Why does no one point out that it's illegal for a 14 year old to work anyway? At one point, the manager of his restaurant actually leaves he and Cathy alone to run the whole place.
*Jill comes back in the end after seeing the picture of him kissing Cathy and asks him out. He just thinks it's hilarious.
*The orange and brown polyester uniforms they wear on the front cover are actually the same uniforms they wear in the book.