I'm guessing you have a column with all of your customers (several entries of the same customer) with a column of dates next to it, but there's only one date present for each customer leaving blank spaces next to the duplicate customer numbers for dates. If that's the case, highlight the date column, go to Find & Select -> Go to Special -> Blanks, and enter the following:
Where A1 is the first date entry that you have (first date, customer #1). This will essentially keep adding a random number between 1 and 100 (you can change these numbers if you like) to the above date until it gets to another manually entered date, at which point the cycle starts over. I think this gets at your question?
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