Dear Prudence,
When I was in high school and college, the main way I dealt with my anxiety was to tell lies. It got really bad, I had to confront myself about it, and thankfully, I cleaned up my act. I’d been very good for a while, but I slipped up in a minor, stupid way.
A couple of months ago, I took a vacation and told all my coworkers I went to a different place that I actually went (something like saying I went to Chicago when I went to New York instead). I have now started dating one of those (now ex) co-workers, and it’s likely that she will at some point be faced with hard evidence that I straight up fabricated a vacation.
I’d like to get out in front of that and tell her—it’s for the best she knows about this (mostly) past problem. But I’m really at a loss with how to approach this conversation. I don’t want her thinking I’m a deceptive, manipulative jerk, but I know it will be hard to convince her that this stupid thing is the only lie I’ve told in years.
— Trying to Be Truthful