Progress the story until you have rubbed oil on Jessie’s back at the Beach, to do that you need:how to get to rub back on jessie and jogging with her
-> You need to have completed the Rave event.
-> Then, you need to have gone jogging with her more than 4 times (weekdays mornings).
-> After that, you need to have offered her to rub some oil on her back at least once. (weekends noon)
Once this is done, go to the Beach any weekday morning at 7:00 am and talk to Jessie.