Trying to Move Data From One Sheet to Another If it Meets Criteria

Question and info is attached.

Excellent question. It's a word doc because i thought i could just copy and paste it on to the thread but the images do not show up so i had to attach it instead. My question is how can i move the header of a table in one sheet to the appropriate cell in another sheet that has a calendar on it if it meets the criteria. Criteria being a deadline in a certain month. I'm really quite terrible at explaining it without the help of images :/
This is the just the text from the attached doc: I want to create a formula or macro (whichever is easiest) that will copy ‘Deadline 1’ or ‘Deadline 2’ into the appropriate column in another sheet that looks like: IMAGE OF THE TABLE There are already formulas in the first table that make it so once you enter the name and date the deadlines are automatically updated (say 30 days from the date). I would like the result to look like this: IMAGE OF THE TABLE Is this possible? Or should I just give up and manually move each deadline into the appropriate cells in the other sheet?

Attached is the small sample thank you.