The timing doesn't quite work out unless several months are going to pass. Since the time jump is 20 years and most girls are 18-years-old at the start of the game (and the ones that are 19+ have accounted for fathers), we'd need a minimum of 3 months to pass before any of the past LIs become pregnant (since, for example, 18 years and 11 months old plus 9 months pregnancy is still less than 20-year time jump).
Certainly a possibility I've considered though.
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