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I have a feeling that Chandler has always sort of had this crush on Monica ever since that one Thanksgiving, he just didn’t act on it afterwards. I mean, there are so many subtle hints from S1 on (him offering to be the father of her children etc). In my head, Monica was always his “the one”, so no other date would ever come close to her.
And probably the most obvious headcanon is that Mondler ended up having at least one biological child together after the show ended. The creators left it fairly open by saying that it’s just unlikely, but not impossible for them to conceive.
Thanks for the question! :)