Wow, that’s pretty rare, usually people have trouble getting to Grace!
The easiest way to see which path to take is to go into the settings and turn on the romance hints, they will tell you which decisions are important and which romance path they lead to.
For Jessie, you have to choose to go into the bar at the start of the game, and then say that you like the music. To continue to pursue her after this you’ll have to go to the bar when the opportunity presents itself and not help Marion with her groceries when you are at the market.
For Marion, you have to help Marion at the market and go back to her house and open up to her, and then go help on their farm when the option comes up.
