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As Jamie is a character youcan romance you can't do any of that, she grow sthe same pace as you.

The option to load is only on the opening screen of the game so you need to close and reopen it

As you can do these in any order the three ways are:

-Curios shop's item

-the fairy

-Tiffany (green haired mad scientist)

For jamie (the boss) I don't know (her boobs progress as the same time as you). For the dark bitch you need to give her a hot dog voucher that you obtain each time you win a hot dog contest. And if you succeded you can even give her a vial.

I just finished the game and I enjoyed it a lot. The gameplay loop is solid and the sense of progression is well done. 

I just found that trying to give an item to a specific coworker (voucher, sandwich) can be tricky if you are unlucky (it took me 5min of non stop day skipping), so I would suggest to add the possibility to visit them like with Lilly.

Also the fortune teller has limited use for now, I don't know what is planned for her but using her to give hints toward the ingredients of the perfect sandwhich would be a nice addition.