Probably not the first one... most likely not the first several either.
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I don't remember how it was described in the books... but in the movie at the end, in addition to Harry and Ginny sending their kids off to Hogwarts, we also see Draco and Pansy. Harry and Draco lock eyes for a moment and give each other a quick curt nod. A gesture that speaks volumes, comming from the two of them.
But teddy was a baby in the ending of the first book (and in the last scene looking to the future he was already grown up) and he is a baby in this pic (i'd say younger than 2 years for sure) so, it kind of HAS to be one of the first christmas after the battle of hogwarts
IT'S NOT PANSY IT'S ASTORIA GREENGRASS, ANOTHER PUREBLOOD PRESUMED SLYTHERIN. Sorry. I'm just very passionate about this. JK Rowling said that you know how the readers didn't like Pansy? Secretly Draco didn't either.
UPDATE: 'Simply Irresistible', the fanfic that the guest mentioned, is not the one I remember reading that perfectly displayed this scenario, BUT it's an absolutely flipping fantastic fanfic that I've almost read all of. It's a beautiful piece of work.
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I don't remember how it was described in the books... but in the movie at the end, in addition to Harry and Ginny sending their kids off to Hogwarts, we also see Draco and Pansy. Harry and Draco lock eyes for a moment and give each other a quick curt nod. A gesture that speaks volumes, comming from the two of them.