According to Jim Recap: An According to Jiminy Christmas

Maggie, mother of Cheryl, Dana and Andy, is coming to visit for Christmas. This isn't a good thing for any number of reasons. For starters, Jim isn't ready to give up his bed. That means he'll need to sleep in one of the girls' beds, and be uncomfortable all night (I guess it's okay if his mother-in law is uncomfortable). But perhaps more importantly, it means that Cheryl will be hiding her feelings the whole time since she won't tell her mom how she really feels.

Ever since Cheryl's dad "left" (which really means that he died - even though this happened a couple of years ago), things just haven't been the same. Cheryl hasn't been able to tell Maggie how she feels. This year, though, things will be different. Cheryl is expecting to receive her grandmother's pearl necklace. But then Maggie gives them to Dana and it's on. Except Cheryl doesn't say anything, despite some prodding from Jim. What is going on?

Jim tries to figure things out, and even tries to suggest that maybe Maggie would be more comfortable in a hotel - which really means that he would be more comfortable with her in a hotel because he could sleep in his own bed - but that doesn't help things at all. In the end, Maggie just gets up and leaves to go visit family before she heads home. So Jim has to grab Cheryl and try to catch her at the airport before things really get bad. At least there, Cheryl and her mom get to talk.

It turns out that she gave the pearls to Dana because Dana doesn't have someone (like Jim) to give her things. Of course, Jim probably doesn't give Cheryl nice things, but that's not the point - just saying something like that means plenty, because it's like saying that Dana has problems, and that's okay. Maybe it will be different next year.

And presumably it was, because by Season 5, in The Gift of the Maggie, Maggie was happily sleeping at Jim and Cheryl's (in Kyle's race car bed, no less) and they were struggling to keep her there. So something had to work out.

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