2 questions.

1) My ultimate goal is to be able to obtain a list of dates within a column.  Is there any way to select multiple dates in a field or do I have to have multiple date fields?  One possibility is to use the multi-select field but I don't know how to automate the dates to be selected.  Is there a way to do that?  keep in mind my ultimate goal and if there is another way to achieve that, I would be open to hearing it.

2) If I have a date, how do I send a reminder email 2-3 days before the date occurs?  

Thank you for your help!