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?
The couple bids farewell to New York while preparing to move to a new Chicago home; Donnie and Jenny search for a delicate way to tell Macky that he will not be moving in with them.
Donnie, Jenny and Evan spend some quality time together in Los Angeles; the family heads to Donnie's Simi Valley house to help pack up for the move to Chicago; Jenny and Jojo search for a gift for Donnie.
Donnie tries to hide his disappointment when Jenny has to travel back to Chicago for an important doctor's appointment and miss the opening night of the New Kids on the Block tour in Los Angeles.
Jenny battles indecisiveness while decorating the new family home in Chicago. She also ends up locking horns with her sister Lynette. On the road with the New Kids on the Block, Donnie is reminded what it means to be a pop star.
After losing another family pet, Macky brings an unwelcome gift of chickens to lift Evan's spirits. Jenny is at her wits end and sends Macky out on tour with Donnie. While Jenny has her hands full teaching Evan about responsibility with the chicks, Donnie gets in over his head as Macky hits on all the fans.
Jenny and Donnie focus on blending their families this week at events that take them all over the country. Jenny and Elijah join Donnie in NYC for a concert at Madison Square Garden, before attending an Autism Gala for Evan. Later that week, Elijah and Evan bond at a local fair in Chicago while Donnie and the other New Kids On The Block revisit their old school where they first performed.
Season Finale - Donnie reconnects with a friend in New Orleans during the NKOTB tour. Back home, plans for Evan's birthday party are derailed when he suffers an unexpected injury.
Donnie has his heart set on buying a new motorcycle to help him keep his edge now that they are settling into suburban life. As he struggles to pass his motorcycle test, Jenny has her own business to take care of at the DMV.
As Jenny and Donnie settle into their new home, they celebrate Donnie's first birthday in St. Charles. Meanwhile, Evan is diving head first into adolescence and Jenny fears her affectionate baby boy is gone forever.
As Donnie and Jenny have settled in to their St. Charles home, they've noticed an increased number of fans coming onto their property. Donnie and Jenny must come up with a creative idea to get some privacy and follow the rules at the same time.
Jenny has her hands full planning an anniversary gift for Donnie and working on the charity auction for Generation Rescue. With a little help from Donnie, the event turns out to be the biggest fundraiser in Generation Rescue's history.
Donnie is being honored at Chicago's South Shore High School, which happens to be only a few miles away from Jenny's childhood home. Joined by Jenny's family, the couple takes a trip down memory lane exploring all the places that shaped Jenny into who she is today.
Donnie and Jenny head to Dallas where Jenny is giving the keynote speech at an autism conference. Once they return home to St. Charles, Jenny wants to show Donnie what a huge impact he's had on her and Evan's life.
Elijah is coming to visit St. Charles and Donnie wants to build a fort for him in the woods behind their house. Unfortunately, Jenny is at home sick, so Donnie has to juggle taking care of Jenny while overseeing construction with Johnny.
When Jenny and her family head to Florida to pitch a show for the Home Shopping Network, Donnie and Macky stay behind to plan a surprise for when she gets back. After spending quality time together, Donnie has a proposition for Macky.
With Halloween just around the corner, Jenny must also face an even scarier event: her 42nd birthday the day after! Donnie has a couple tricks up his sleeve to take her mind off getting older.
