Category: Courting Disaster

Courting Disaster, my weekly comic about sex, love, and relationships updates every Friday. You’ll laugh your pants off.

This week’s question…

A reader writes… Q: I’m a 39-year-old guy, happily divorced. This summer I re-met a very special woman whom I knew growing up. We get along very well and are having a great time together. While I was divorced, I had an affair with this woman’s friend (who does not live nearby.) To be fair, I spoke to the woman with whom I had the affair about seeing her friend. While it felt strange, she wanted the best for me and her friend and encouraged me to pursue her friend. Also, I had been hyperactively dating on match.com for quite some time (which I heartily recommend) and have slowed down to focus on my new relationship. I’ve discontinued my match.com membership, have been cleaning house of lingering relationships, deleting mobile numbers and e-mail address and the like. Meanwhile, I’ve been honest to these women about why I’m doing this and trying to part as friends. I am doing my best to minimize temptation. Disclosure is my question. I want to be honest with this special woman yet, I don’t want to shoot myself in the foot. In the spirit of honesty, should I ‘fess up to this short affair with her friend, which happened in the past year? Should I ‘fess up to the magnitude of my hyperactive match.com dating? Or might I be best off let sleeping dogs lie?

Don’t answer here… go on over to the CD site and offer some advice.