It's not dumb... it's a very legitimate question I have to answer.
The truth is...I have no estimated date for the next update. My initial estimate was May 15th but I'm nowhere close to finish what I have planned for the update, even worse I'm at the middle of the content. The planned content is: 1 first day mission, 3 optional missions, 2 optional dates with dalton, 5 daily jobs (with a first day/repeat versions) 3 story missions and 3 romance missions (these are the missions that progress the romance meter with dalton) and the endings, and so far I have the first day mission, the 3 optional missions, 2 dates with dalton and 2 daily missions (I'm testing the 2nd one today) so I'm nowhere close to finish them by next week.
It would be a lie if I gave a date... my estimates are really bad. My new one is June 15th but I don't want to set it on stone. That's why I decided to do a weekly report, to keep everyone informed what I did on the week.