I don't even have the date option appearing. As soon as i reach the correct time (midnight) it tells me I missed the meeting because I wasnt in the office at that time. I've even tried to stay in the office and advance the time to midnight but it wont let me do that past 8pm.
I assume its a small script error. In the game code, could it be that you (Andrealphus or whoever coded the game) forgot to add a special condition letting us stay in the office if we have the Cassidy meeting active?