Dear Prudence,
I have a wonderful boyfriend of over a year, and I’m convinced he’s the one. However, we’ve had an on-and-off issue where he gets uncomfortable whenever I go out without him. This isn’t a frequent problem, but once or twice a month I’ll go out to a bar for happy hour or a girls’ night out. I know that he trusts me, but he always texts while I’m out asking if there are lots of guys wherever I am and if they’re hitting on me. The other day, my friend was running late to an after-work happy hour and he insisted on meeting me there to “keep me company” until she arrived, but I know his motive was to make sure no one hit on me as a single woman at the bar. I know where this is coming from, as he was blindsided when his ex cheated on him years ago, subsequently ending the relationship. He went to therapy afterward, but clearly this issue still manifests itself in his insecurity when I go out alone. This isn’t a deal-breaker for me, but is there anything I can do to try to lessen these “protective” measures?