Are the dudes OK?

Sort of...But things are getting weird

My grandfather was a guy by the name of James (Jimmy) Price. Jimmy was married 4 times, with 2 long term girlfriends. I have a riddle for you: why was this the situation?

• He made money

• Did not cheat

• Didn’t hit

• He gambled, but, and I mean this as a kid who had gotten solid at Gin rummy who played him straight up for a couple hours who never won a single hand…