Weekend At Bernie Madoff's

I had a nice first-date dinner with a guy I met on a dating app. Afterward, he said he had something to show me, pulled up his pant leg, and revealed an ankle monitor! He said he hadn't wanted to put it on his dating profile, and "It was just white-collar." (I Googled. Embezzling money. He's on "supervised release" -- apparently with some range beyond house arrest.) This situation bothered me, but I accepted his invitation for a second date, given our chemistry.

--Shocked

Ideally, if a man wears "statement jewelry," the statement it's making isn't: "I'm in constant communication with my parole officer." A guy who embezzles money -- assuming there's no "my brain tumor made me do it!" -- is likely low on the personality trait of conscientiousness. Someone high in conscientiousness is disciplined, dependable, organized, and shows concern for others' needs and feelings. In contrast, those short on conscientiousness are unreliable, careless, impulsive, and poor at delaying gratification. (They probably see little reason to do it, as they also have an "eh, whatevs!" attitude about their effect on others.) Personality traits tend to be pretty stable over time and in various situations -- though research by psychologists Nathan Hudson and R. Chris Fraley suggests people can work to change their personality by repeatedly changing their typical behavior. For example, a usually inconsiderate guy could act like a person high in conscientiousness, starting in small ways, like making the bed every morning instead of leaving it for the girlfriend-slash-housekeeper to do. That said, lasting change might not be possible without strong motivation to mend one's ways -- like feeling deep remorse at all the people one hurt. (Remorse at getting caught doesn't count!) This guy's "it was just white collar!" is not exactly dripping with contrition. You could get him on the phone before your date to probe further into what he did and his current perspective on it. Is he passionate about turning over a new leaf, driven to be honest -- or just to seem honest? As for your "chemistry!" argument for seeing him again, consider that you get the whole dude, not just the hot parts. Wanting to see the best in somebody doesn't make the worst in them disappear. It just might be a while before you arrive home early and spot it -- in bed with your best friend, your sister, and the UPS lady. ... For pages and pages of "science-help" from me, buy my latest book, "Unf*ckology: A Field Guide to Living with Guts and Confidence." It lays out the PROCESS of transforming to live w/confidence.