Chelsea is a hopeless romantic, those are annoying
How much have they been fukking that he felt he needed a breather from that
Chelsea makes no sense to me.
She says she's a nurturer type -- in my experiences, those types tend to be hard to care for because they are so used to doting/caring for others to where they don't take time for self-care or for someone else to do it for them -- but needs constant 24/7 reassurance of her place in one's life. That math ain't mathing, and Jimmy ain't wired to constantly reassure like that.
Jess is probably the better choice for him solely because her self-esteem is higher but that ship sailed.
I'd be shocked if any of these worked out.