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So it's 1998, and Regina is by herself, desperate for her kids to come visit. Luckily, her friend comes by just in time to see the sink explode, so she calls a handyman.
In 1960, Eli and Penny are getting ready for Christmas. Eli is very stressed because his dad is staying with them, and he's less than thrilled, though he freaking looks great. Eli is the author of a bestselling book, but his dad is not impressed. Eli's son just wants him to help finish the time capsule.
Then in 2015, Jessie is helping her sister plan her big Christmas wedding. Beth is getting nervous, though, and it keeps getting worse. Her fiancé calls and says the business that was handling everything just went out of business. But Jessie is confident: "We can definitely do this!" Then the bad news keeps coming. Jessie's ex-boyfriend Tim is the officiant, and the wedding is going to take place in her backyard.
So Regina's whole thing is that the handyman shows up and just kind of sticks around. It's Nelson, her future husband, but for now he's just the handyman who is sticking around. However, he doesn't know anything about pipes, which is a problem.
Eli and his son are working on the time capsule, but Eli's dad is very grumpy about it.
And Jessie and Tim just kind of have to keep being around each other.
Ultimately, everything works out. Eli and his dad have a heart-to-heart, and they finish the capsule and bury it in a titanium box. 
That box is what led to the tree root hitting the pipe that burst in 1998. They end up finding the box and open it up and yay for them. 
And Jessie and Tim had their one and only date locked in the school gym in 1998. In 2015, they finally make up, and the wedding is great. They end up kissing, and everyone has a happy ending.