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You could do the following
Segmentation with two Segments: Clicked X in Past; Field in Database
Then in your email, you would Segement by for that block.
Two emails that go to each group. Might be easier to do this if you don't plan to use those Segments often.
i actaully poked around for a bit and created a smart campaign to change the data field to the link they clicked based off a part of the link. Then based off that used segemnts and within those segments used tokens to populate the correct content.