Devon Fremont transfers to a prestigious prep school, Northwood Academy, for her sophomore year of high school. She hangs out with her best friend, Emma, and three others: Cassidy, Abby and Bryn. Devon quickly becomes bored with the school and the lack of attention from boys. Devon suggests the five girls create a secret club called the Dating Games (DG), where they all find each other dates for the homecoming dance.
Bryn is openly excited, while Abby cautiously joins. The only girl who hesitates is Cassidy, who made a pledge the previous year not to date. Devon manages to talk her into joining, but Cassidy has reservations. The five friends create a set of rules for the DC club. They want the dates to be casual and fun and agree to help each other find good guys with the right intentions. With this in mind, they mention abstaining from sex on their dates. They also make a point to put their friendship before these guys, and not to go after each other's dates.
The girls talk about their crushes. Devon talks Emma into a makeover, and she reluctantly lets Devon's aunt give her a shorter haircut. Although Emma feels glamorous with her hair, makeup and eyebrows done, she increasingly notices that she and Devon have little in common, aside from having both lost their fathers to divorce a few years earlier. Devon can be brash and bossy, and sometimes abuses her freedoms. Emma, on the other hand, is unassuming and gentle, and attends church regularly with her mom. The girls decide to go over to Bryn's house to pick out new clothes for Emma. Meanwhile, Abby is driving home from a wedding with her parents when she tries to convince them to let her go to homecoming. Her parents are excited, but her dad is a bit skeptical since he hasn't met her date. The other problem is Abby's crush, Kent. He doesn't know he's taking her to the dance yet.
The DG club begins to fall apart when Devon sees Bryn giggling with her crush, Harris, the guy that Devon decided she wanted to go to homecoming with. Little does she know that Bryn has also liked Harris for a long time. She forgets her anger when the girls come up with goofy nicknames for each other and the guys they are going after. They single out Cassidy for the next makeover, and plan to go dress shopping that weekend. Cassidy insists that it is bad to focus too much on appearances, but Abby, Bryn and her older sister, Tara, coax Cassidy into letting them cut her hair and give her a facial. Emma also finds out that Cassidy's crush, Lane, has liked her all along. Later that evening, Abby apologizes to her mom for going dress shopping without her and gets a message from Kent asking about homecoming, but not asking her to homecoming.
The next day, Devon comes across an opportunity to talk to Jason, the most popular guy in school, for Bryn. The only problem is, instead of talking about Bryn, Jason keeps flirting with Devon. This leads to confusion, and Devon wonders if she should go to the dance with Jason, and Bryn could go to the dance with Harris, instead. Meanwhile, Cassidy is thrilled because Lane finally asked her to the dance. Later on, Emma's crush, Isaac, asks her, too.
Despite all of the good news, Cassidy is concerned that she might be ignoring God in choosing to take a date to the dance. She calls her youth leader from church and asks her for some advice. Her mentor doesn't give her an answer but reminds her that sometimes people try to get ahead of God and make up their own rules to impress Him. She reminds Cassidy to spend time with God, and to have a relationship with Him, not just a set of rules. After praying over it, Cassidy decides to go with Lane to the dance, but to focus on treating her friends in a way that would be uplifting to God.
At the end of the week, Bryn realizes she is running out of time to get a date, and decides to take matters into her own hands. Strutting like a celebrity, Bryn flirts with Harris, hoping to make Jason jealous so he will finally ask her to homecoming. Instead, Harris asks her out, and Bryn decides that she would really like to go with him anyway. Devon is slightly unsettled with the change of plans, but likes the idea of going to the dance with Jason. Abby is still waiting on Kent, so Bryn asks Harris to convince him to take her to the dance. In the bathroom, she overhears two girls gossiping about Jason and Devon. One of them is Jason's ex, Amanda, who says that she broke up with him because he treated girls like objects. Bryn wonders whether she should tell Devon about the conversation.
After the girls receive a text from Devon saying she's going to cancel their homecoming plans because she doesn't have a date, the girls meet at the coffee shop to talk it over. Bryn tells Devon what she overheard about Jason, and offers for Devon to take her friend Darrell to the dance instead. Devon is displeased and storms away before she can hear Cassidy's offer to host a nice dinner at her house before the dance.
When Emma returns home, her mom tells her that her grandfather died of a heart attack. Emma is upset and considers skipping the dance. When Emma talks to Devon about it, she blows her off and is completely wrapped up in her plans to get a date with Jason. Cassidy, however, is kind to Emma and offers her a ride home when Devon forgets to pick her up. The next day, Emma explains to Isaac that she might not go to the dance with him. To her surprise, he is very understanding and explains that his mom died of cancer a few years ago. He assures her that she will see her grandfather again in heaven and that it is fine if she doesn't want to go to the dance.
At lunch, Devon brags that she finally got Jason to take her to the dance and that he is taking her to a restaurant for dinner instead of going to Cassidy's house. The night of the dance, the girls get ready for dinner, and Bryn fixes Abby's dress since her parents don't like the one-strap design. While the four girls and their dates have an elegant dinner, Devon and Jason go to a cheap restaurant, and Devon begins to realize what she is missing. After the dance, the girls plan on meeting at Bryn's house for a sleepover. Devon tells them she'll catch them later and not to wait for her.
While the girls go over how well their dates went, Emma gets a call from Devon asking if she could pick her up. They find her sobbing out by Henson Reservoir, looking disheveled. Devon explains that they were just going to see the moon on the lake when Jason starting acting pushy. Devon kicked him where it hurts, and he drove off, leaving her alone by the lake. The girls take Devon back to Bryn's house, grateful that she is OK.
The next day, the girls meet at the coffee shop and decide to keep the DG club together. They decide to pick blind dates for the next dance, a masquerade ball for Halloween.