First time playing this game so I am following the walkthrough for my preferred path.
Found a mistake in the code for 2.scene_movein.rpy. There is no call-out for $ dar_upset1 which means the coffee date with Jen cannot go down the non-cuck chat route.
Not being a coder myself, I am not sure if it is as simple as writing that line in 2.scene_movein.rpy after the jel+1 and ang+1 lines or not.
Edit: I just edited the script for that scene and it now works correctly, but this brought up another issue. At the end of the coffee date with Jen, if you are on the "Don't talk about Darrel" side, you are not supposed to see the car scene (according to the walkthrough). Not sure if it is a script or walkthrough issue this time. Just FYI.