Rushed it before posting,
Even with rewind time the fastest I could get to date 2 was the first Thursday.
Now I'll focus on Sam and personally see how the revenge path is concluded.
Interesting stuff. Obviously, in a regular playthrough one won't be able to get all the required stats / love / Kink points in time (let alone fire off the events), but does give non-cheating players some ideas on what is possible. In an old version for instance (20.11 if memory serves) I was able to get Sasha up to 80 LP, and quite a bit of kink (60+) in about 17 game days (on normal difficulty). That is without starting with the guitar skill and with training for martial arts! - add in no car to start with), which obviously delays things quite a bit (since I did want to join the band), or using any of the cheats to make things easier.
The game is gloriously complex with so many things dependent on each other, add in some constraints (skills, attributes, seasons), that it is good to see how quickly events for characters can be fired off successively. And which characters 'cluster' together, since there is only so many women you can chase in a day.
And one might also accidentally running into constraints one had forgotten about (like not being able to get a notification for the work party on Wednesdays; needing a beach meet up with Ayesha just after summer ended). Which can then seriously derail one's run.