Corrected entry: When Jack and Just Judy go out for a drink it is Christmas Eve. They share an awkward kiss and he goes home. Yet shortly afterwards they are both arriving at the School Concert together - this is also Christmas Eve. The scenes are either back to front or the first date was not Christmas Eve and the title saying it was came up at the wrong time.
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Correction: I had to see this movie a few times to kinda understand it, but the movie doesn't go from start to finish in one straight line. When Jack and Just Judy are kissing, it IS Christmas Eve, and they kiss, and that is the end of their night, but the Christmas concert is earlier in the evening, and they go to the concert, and then they are standing on Just Judy's doorstep afterwards. I still don't understand why they would be going to an elementary school's Christmas concert in the first place, but whatever, not for me to judge.
John's brother is going to the pageant, and invited John, who invited Judy.