
There’s only one way left for Jimmy in Season 4
If we get season 4 and Jimmy and Kara remain friends, then there’s only one real love interest left as an option for Jimmy. He’s currently dating her in the comics and she’s in the show.
Siobhan getting a small character arc and reforming along with Intergang through Jimmy’s help would be a risk but I think could pay off nicely if done well. Jimmy using the failures he went through in season 3 could really be meaningful to not only help someone else be better but also gain him a new love interest because he himself learned to truly be better.
The main problems with this are that Jimmy would have to hop off the ship he has with Kara that was built and dismantled over the course of about 2 seasons, so there would be obvious backlash from fans. There would be the possible jealousy aspect from Kara’s (or even Siobhan’s) side to deal with and then there’s what to do to incorporate Siobhan into the main group if she and Jimmy get together. Siobhan herself is not a very popular character or a main one so she’d have to work from the ground up. It would be an extremely controversial decision if ever made.
I think the main thing I would like to see from this hypothetical scenario is Jimmy teaching Siobhan that it’s better to gain respect through helping others and references Superman and Supergirl and all they do to help people. It would also be nice to see Clark being a sort of role model/big brother figure to Siobhan and Intergang.