cant seem to go to the doctors office at night (the latest i can get to is 23:38 but i then the option to go to the place isnt available and when im there earlier 18-20 or something nothing happens)
To go on first time: go there at the end of day 2.To return: complete the main quests first, wait for a call on the following day, then you'll be able to go back to her after 18:00 on weekdays.