In an effort to reconnect with the girls, Annie reinstates an old tradition of "Family Night," even though the adults are all now divorced. Of course, nothing goes right: the girls try to escape; Nikki becomes outraged after learning that Gary is dating someone new; and Annie is thrown for a loop when Jack shows up with a hot date.

There is a father-daughter dance coming up, but Matt is unable to attend so Jack volunteers to be Sophie's date.

Annie reluctantly agrees to let Sophie start dating a sixteen-year-old boy and is pleasantly surprised when she sees the positive influence he has over her, until he reveals a little surprise of his own. Meanwhile, Jack agrees to help Mackenzie on a school report about the court system and, in return, gets makeover advice from both Nikki and Mackenzie when they decide he needs a little "flash" and "pop" in order to win a court case he's worried about.

When Sophie tells Annie that she does not care about getting good grades, Annie decides to set an example by taking night classes at the local community college. Nikki joins her in a Spanish class and is surprisingly fluent as she frequently watches telenovelas. Meanwhile, the dads are in charge of getting the girls to finish an important school project.

Annie steps outside of her comfort zone when she accepts a dinner date with her former Spanish instructor, Alex. Meanwhile, an envious Jack runs a background check on Alex and discovers that he is hiding a secret that Jack and Nikki decide Annie needs to know about.

It's Spring Break and Annie decides to take the entire gang on a road trip in Matt's tour bus. Annie and Nikki think the road trip will be a great opportunity to spend quality time with the girls. But togetherness starts to wear thin as the girls are anything but thrilled to be trapped with their parents in an RV headed for the Ozarks.

When Principal Diego breaks up with her husband, Annie and Nikki befriend their now-vulnerable nemesis to get her to write letters of recommendation for Sophie and Mackenzie, who are applying for a competitive college prep summer program. Meanwhile Matt asks Jack's assistant out on a date despite his objection.

The mothers throw Sophie and Mackenzie a double birthday bash, but trouble abounds when the girls want a Mad Men party.

Sophie and Mackenzie try out for the cheer squad, but when Sophie gets picked and Mackenzie doesn't, this causes friction between the friends and mothers. Meanwhile Matt and Gary need to cut the worst player from their basketball team, Jack.

Mackenzie and Sophie are invited to a seniors party but Annie has her concerns.

Sophie is desperate to go on a school ski trip but financial issues get in the way.

Sophie sneaks out to a concert and Annie is less than impressed.