The mothers throw their daughters a double-birthday soiree, but the teens think it's lame and demand a "Mad Men" theme for the bash. At the party, Sophie is mortified when Annie's ensemble gets too much attention from the teenage male guests. Meanwhile, Matt seeks Jack's help after forgetting to buy his daughter a birthday present.
Principal Diego and her husband separate, so Annie and Nikki try to befriend her in hopes of getting the vulnerable administrator to write letters of recommendation to a college-prep summer program for their daughters. Meanwhile, Matt asks Jack's assistant out on a date, despite Jack being against the idea.
Annie is upset over Sophie's lack of concern about her school grades, so she decides to set an example by returning to school at a local community college. Nikki decides to join her and enrolls in the same Spanish class, where she proves most proficient in the language because of her fondness for watching telenovelas. Meanwhile, the fathers are put in charge of seeing that the daughters complete an important school project on time.
A reluctant Annie allows Sophie to date an older teen and is pleasantly surprised by the impact he has on her daughter. Meanwhile, Jack helps Mackenzie on a school report about the legal system, so she and Nikki thank him with a fashion makeover.
Annie and Jack suspect that irresponsible Matt will be a no-show for Sophie's father-daughter dance, so Jack readies himself as a fill-in. Meanwhile, Mackenzie worries that Nikki's appearance at the event will prove embarrassing.
Annie reinstates Family Night in an attempt to bond with the girls. Problems arise when the teens try to escape, Nikki learns Gary is dating and Jack shocks Annie by showing up with a hot date of his own.
Two single moms (Jaime Pressly, Katie Finneran) who are best friends struggle to raise their spoiled, mean-girl teen daughters, who are also best friends. In the comedy's opener, the teens lock a student in a school bathroom and their moms won't let them go to a dance as punishment.
Sophie and Mackenzie try out for the cheerleading squad at school but only Sophie lands a spot, leading to friction between their mothers. Meanwhile, Matt and Gary need to cut the worst player on their basketball team, Jack.