The only lizard dude in a cell I'm aware of is Cicero, and AFAIK your choices of what to do with Bradley and Rylan don't affect your ability to release Cicero at all. (Also, you can "side" either with or against Bradley and Rylan completely independently, so you're not really taking sides.) You just have to go back to the pirate base after leaving.
I don't think there is a dating route selection. You can choose to date people or not (if they have dates available; most haven't been implemented yet), and choosing to date someone doesn't seem to affect your ability to date others.