SHERRY: Well, it’s a work-in-progress. It was so bachelor pad before: rock posters, modular furniture, magazines everywhere.
When Sherry leads Lorelai and Rory into the apartment she shares with Christopher, we can see it is the same one they lived in at Christmas 2001, even though Christopher told Emily and Richard he and Sherry were looking to buy a new place of their own. The buying a new place story was another of Christopher’s untruths, because Sherry says nothing about them hoping to buy another home, and talks of this one as a work-in-progress, as if she hopes they will continue improving the one they already have.
The odd thing is that Sherry talks about the apartment as if it was one Christopher lived in alone before he got with Sherry, calling it his “bachelor pad”. That doesn’t fit in with the story we heard from Christopher, which is that he lived in Berkeley until he met Sherry, after which he relocated to Boston to be with her – and would have presumably moved in with her, or they would have moved into a place together.
From what Sherry says, Christopher was already living in Boston by himself, and Sherry moved into his apartment (where did she live before that he didn’t move in with her, when she apparently makes more money than he does? With her parents?). Did Christopher meet Sherry in California, and then move across the country and get an apartment in hopes of being with her? Which is weird and stalkerish, and seems like way more effort than Christopher would put in? Or did he move to Boston independently, and meet Sherry there?
It seems as if Christopher cannot tell people one simple thing which is verified by someone else. It’s as if everything about him is a lie. Christopher as a character barely exists.