>>33265501He's thought about it, it all depends on if he actually gets to settle down. He's a career criminal trying to make as much money as he can without too much risk, but his methods vary. He's a Solomani working in the Spinward Marches. He's the pilot for the party, they do a lot of the hardcore crime while he collects a share and does some smuggling. His plan is to retire, but it's not as if his job comes without risk no matter how much combat he avoids.
As for a family, maybe. He's a bit severe and highly individualistic personality wise and also, there's the fact that he's a criminal. So far he's avoided making enemies, though his associates have plenty and his continued partnership with them could mean they might come after him as well. He also doesn't like kids, too much of a responsibility and he's pretty sure that he'd be an awful dad.
So tl;dr, he wouldn't be opposed to getting into a serious relationship if the woman was understanding or he might just lie about his past after getting out, but he knows that's a dick move. Definitely no kids though.
