Setting date picker date and having 2 columns to each date for excel calendar

Hi, Its hard to give a good description of what the problem in the short title, so im going to explain it here. This file is a leave tracker for staff and users will either forecast their leave in advance or fill it up when they come back from say medical leave.
First problem: On the userform, textbox1 and textbox2 when clicked, shows a date picker. It currently shows today's date when it pops up, which is fine. What i want to achieve is when a user selects a date that is maybe 1 month ago, for example 7 Nov 2017, i want the date picker from textbox2 to show 7 Nov 2017 rather than today's date again.

Second problem: I have received feedback that users would like to split the date into AM / PM to facilitate multiple entries on the same day. For example, a staff may want to take half day annual leave in the morning and half day child care leave in the afternoon. Current file format does not support more than 1 entry in the cell other than putting the second leave type into a comment box.

Have attached the file and print screen of the outcome for problem 2. Any help is appreciated.