The Infidelity Question

A listener needs our help: Should he be honest about being unfaithful two years ago, now that he's considering proposing?

June 1, 2017

He didn't want to be identified, but he sent us this message and simply asked: Do I tell her? 

"I have been dating a woman for nearly three years.

Two years ago, when I had a two week fling / affair / thing with a female that my girlfriend doesn’t know about.  Other than the people involved, the only person who knows about this situation is my sister.

This is the only time I have ever been unfaithful to anyone. Even writing that sentence makes me sick. I hate myself for what I did.

I want to propose to my girlfriend over the summer. My sister thinks it is MANDATORY to tell her about my mistake before popping the question. That when you get married, full disclosure is required.

The only other important detail to share is that there is zero chance I will have any contact with the ‘other woman’ again. She was visiting town for one summer. We aren’t friends on any social media and I don’t have any way to contact her. We don’t work together. It was just a thing between two strangers who are now strangers again.

So: Do I have to make this terrible confession before I propose?"

The team here discussed and we all had plenty to say, including a couple very insightful listeners. And of course, one of Jeff's questionable analogies made it into the conversation as well!