with the above table being in A1:C6 (with row being headers) something like the below *might* work:
where E2 holds Name of interest (e.g. Jess), and F1 the Month of interest - e.g. Nov-19
obviously if you add more names in Col E, and months in row 1 (G1 etc) you can copy across to generate more results.
I say *might* as there appear to be some duplicates in your dates and unclear to me, given lack of expected results, as to whether or not these need to be ignored
as-is the above, for Jess, would generate 1 day in Oct-19, 2 days in Nov-19 & Dec-19.
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