Melissa's Extra Objective is finicky/buggy. First run I do Melissa's first, talk to everyone inside then do her tasks, hug her afterward, Extra Objective. Second run I do Melissa's after Phoebe/Quinn/Teely, speedrun the tasks, quickly change screens to trigger the opportunity for the hug, but no conversation, so I talk to everyone inside then try again, still no conversation, no Extra Objective. Third run is a repeat of the first, Extra Objective. Fourth run is in progress I'm going to speedrun again but do it first. (Attached below is the save from the second run before I accidentally save over it.)
UPDATE: Fourth run yielded Extra Objective.
UPDATE2: Yeah something I did in that second run screwed it up, whether not doing it first or doing it (right) after Teely or after the other two messed something up.
UPDATE3: I remembered something that might be relevant, I triggered Quinn masturbating in the library after Phoebe's, I did not in any other run.