A hammock and soothing nature sounds is all a man needs, right? Wrong. The time has come for Jack to finally settle in, yet he has been avoiding getting his stuff from storage.
He is forced to seek help for the tedious task of sorting out his past life, so he recruits his co-workers, who are surprisingly eager to dive into the world that is Jack. He is not one to use social media to share every aspect of his life, this boggles the Millennials minds since they are connected to everyone and everything 24/7.
Jack comes back with pizza, and his life has become a real life “Facebook”. They sorted out his lives into a “timeline”. Old photos, 90’s memorabilia, and memories Jack wished would’ve stayed buried. An old tape player is discovered, the voice of his lost love strikes a chord, a bad one. While Jack is dealing with the painful memories (gasp! He actually has a heart?), Mason and Clark decide it would be a good idea to put together a 90’s themed party.
The story of Jack’s big ex is finally revealed. Jesse and Jack had been together for two years, and when he went on his first assignment she packed up and disappeared out of his life forever. It struck a chord with Emma, who stayed up all night tracking down every piece of information she could find on Jesse. She convinced Jack that he deserved answers and to find closure. She planned a “chance” meeting at Jesse’s favourite coffee shop.
This couldn’t possibly go wrong, now could it? Just like Emma had predicted, Jesse showed up and Jack got to see her for the first time in years. She seemed to be living a picture perfect life. Married with children, happy and successful. Oh, and the reason why she left Jack? She was cheating on him, and Eddie convinced her to leave him. It may not be the closure he thought he would get, but it was something.
Rightly so, Jack was upset. Eddie had kept the truth from him for all these years. And as Jack cools down from confronting his best friend, an unexpected enlightened moment comes from Clark (who has decided to dress as Jack from the 90’s for the party). If Jack settled down, he would’ve missed out on all the adventures and experiences, and hot hook ups. So in a way, Eddie did him a favour.
Hugs are had. Forgiveness is given. And the 90’s are alive and well. It makes for another entertaining episode.