Jack had regrets. Of course he had regrets. Admittedly, he kind of anticipated that Bob would screw things up. He even thought of finding Bob and telling him specifically what to say. Their entire history up until that point had led Jack to believe that Bob would, in some way, screw things up.
So why did he go ahead and tell Bob to cause a stir anyway? It was simple. Jack… thought it might actually be kind of fun. Looking back, every time Bob caused a scene, it was absolute chaos and sometimes even nearly killed them. But looking back, it was also a lot of fun.
What was a little challenge here and there? What was the point of life if all he focused on was working and not having fun? After all, he'd decided to do all the serious stuff as Lex, while living slightly more carefree as Jack.
After all, unlike Lex, Jack had no pressure weighing down on him, such as the threat of his Inn being discovered as an unguarded treasure trove. At most he had that pesky karma weighing him down.
