Jimbo as Dear Prudence: My wife thinks she's great at socializing. Yikes.

This special edition is part of our Guest Prudie series, where we ask smart, thoughtful people to step in as Prudie for the day and give you advice. We asked Jimbo to weigh in on terrible conversationalists, a New Year’s Eve kiss, and contentious band members: Dear Prudence, Three years ago, my wife and I moved away from the town we lived in for 20 years. Get Even More Advice From the Dear Prudence Podcast Dear Prudence, I hung out twice with a guy I met at a friend’s New Year’s Eve party. Honesty is sexy and since you said “you didn’t like him,” I would have maybe been a bit more direct about your personal connection…or lack thereof at the time. But the fact that my boyfriend could develop a close relationship with someone who put me down so much feels awful like he doesn’t think it’s a big deal.