As Donnie and Jenny's wedding day gets closer and their schedules crazier, Jenny goes ahead to Chicago for final prep while Donnie is stuck with the unusual task of getting her dress there in one piece. Also,Donnie nervously awaits the tour bus arrival of his mom Alma, who doesn't fly, and preps a special wedding surprise just for her. And while Donnie and Jenny get ready for their big moment, Jenny's son Evan, Donnie's NKOTB bandmates and the rest of their soon to be blended families help them realize just how lucky they are to have a second chance at happily ever after.

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".

Jenny pushes Donnie to take better care of his health after Macky gets a medical scare.

As the newlyweds continue to figure out co-parenting, Donnie urges a reluctant Jenny that the time has come for 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 could 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.

Jenny and Donnie decide to wade through the many boxes in their garage filled with keepsakes and mementos from their pasts. Together they unearth some forgotten (and slightly embarrassing) items from yesteryear that trigger hilarious and emotional memories. By rummaging through old NKOTB memorabilia and prized family home videos, they might just find a way to take their next steps together as a blended modern family.

Donnie and Jenny both have kids from their previous marriages, but being newlyweds opens up a question--should they have a baby together? Or should they enjoy this third chapter of their lives as parents of fast growing kids? As they weigh the pros and cons, Donnie's friends and Jenny's sister, JoJo, aren't convinced that the couple can still handle a newborn with their busy schedules. So, to test their theory, the gang forces Donnie and Jenny to put up or shut up.

A stressed out Jenny is an unhappy Jenny so Donnie whisks her off on a romantic getaway for a much needed break. When these two get together things never seem to go as planned. What the lovebirds hope to be a relaxing night at a swanky hotel turns out to be anything but, especially when sneaky butlers and midnight kitchen raids come into the mix.

When Donnie and Jenny's busy schedules finally sync up, Donnie plans a McCarthy family trip back to where it all started--the Hotel Baker. While Donnie is anticipating a simple McCarthy family reunion in Chicago, the time home makes Jenny consider a more permanent move to put down roots. Will Donnie really leave the East Coast for the Windy City?