This seems like it would probably be more of a time series problem. You could check out Time series/ sequential data study group - #902 by oguiza and see if that is helpful. Otherwise I might not be understanding your problem fully. My understanding is that collaborative filtering is usually a good choice for matching two groups together that might be fairly sparse. Things like shopping recommendation systems (Person A bought items 1,3, and 6, Person B bought 1 and 3, and Person C bought 1 and 6. See if Person B or C is interested in item 6 or item 3 respectively).
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