Jenny flies to Chicago to make final wedding preparations while Donnie is tasked with transporting her wedding dress; Donnie plans a surprise for Alma, who is traveling to the happy occasion by tour bus.

Jenny and her twelve-year-old son, Evan, have always been a team, so when Donnie offers to handle all things Evan for the day, Jenny is weary of handing over the reins. Donnie tries to juggle his busy TV schedule with his new responsibilities as a stepdad and Jenny tries to trust her new husband with their blended family--but sharing the load might be much more difficult than she imagined.

When Jenny's single dad, Macky, lands his first date in a long time, Donnie and Jenny decide they're going to get him ready for the big occasion. As the big day approaches, it becomes clear that Donnie and Jenny have very different ways of preparing for a date--and Jenny may have a more personal reason for putting her father through so many "improvements.

When Macky gets a scare at his annual prostate exam, Jenny becomes obsessed with convincing Donnie to get checked as well. Easier said than done for a Wahlberg! As Donnie stubbornly procrastinates, Jenny pushes him to take his health more seriously. Wise words from Macky and NKOTB bandmate Danny Wood persuade Donnie to rethink his position and ultimately give the newlyweds understanding that marriage is all about taking care of each other.

As the newlyweds continue to navigate co-parenting, Donnie urges a reluctant Jenny that the time has come to have the dreaded "talk" with Evan. While a notoriously open person in her public life, when it comes to her own child the normally unreserved Jenny is at a loss for words. Thankfully she has the two men in her life, Donnie and Macky, to help her figure out the best way to have this awkward conversation with her growing son. It's just the birds and the bees. What's the worst that can happen?

Jenny heads out of town with her sister Jojo and dad Macky for her Dirty Sexy Funny comedy tour. Meanwhile, a lonely Donnie arranges a road trip to Boston for a weekend of bro-time with his friend, Johnny, and NKOTB band mate, Danny Wood. As the weekend progresses, and the phone calls rack up, it becomes clear that Donnie and Jenny might not survive the time apart--especially with their friends' incessant teasing.