Meadow and Chris? Never

Interesting theory, but...

DC often uses GF references in the show. Not because he's running out of his own original material, but as a "nod" - as a tribute to GF. A prime example is the scene at the funeral parlor when Livia dies. And that's just one of many we've seen, and many that are likely to come.

As for Meadow and Chris: Chris is not like Tony. Tony is, on some level, searching for that beautiful, loving, intelligent, Italian woman: Like Melfi, like Gloria, like Annalisa. He even thought about Ade, in terms of starting a new family. Tony sees this possibility as something completely separate and distinct from the numerous affairs that he still plans to have (or expects to have) down the road. Interestingly, if Tony were not Meadow's father, and Meadow were, say, 10 years older (college graduate, professional, etc.), she'd be the kind of woman that Tony might be interested in.

Chris, on the other hand, is all about his goals of moving up in the organization, writing a screenplay, and having a son to carry the Moltisanti name. He cannot relate to Meadow at all, and she would not want to be with another guy who would think that "oblique" is a Spanish word.

So, even if they were complete strangers who met at some club, Chris and Meadow would find too much at fault with the other to ever hook up. Now, add to this the fact that they are cousins, and the possibility is about as much of a longshot as you can get.

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