Dear Married but Bored

I started dating someone I like a lot. I’m sure the whole “past relationships” talk is going to come up. I hadn’t dated for a year and a half, and before that I had an emotional relationship with a married man. The physical never went beyond kissing. It’s something I’ve grown from quite a bit ,and I see the error of my ways.

I feel like I should tell him because I grew from it and at one time it was a big part of my life.

However, I don’t want to “brand” myself negatively in any way to him early on. Can you give me guidance on this?

We say

We could argue it’s not anyone’s business. However, there’s a lot to be said for being open about the things that shaped you. Not only does it allow the person you’re seeing to get an honest look at you — frailties and what we do about them are the Rosetta Stones for who we are — but it also gives you a chance to see how he handles your frailties.

You don’t want to go the distance with someone only to find he holds people to exacting standards, or dwells on the negative to the point where he can’t trust anyone who has ever swerved into the breakdown lane, or sees one admission of wrongdoing as a mandate to dig into everything you’ve ever done to see what else you’ve messed up. You want someone who takes mistakes seriously but also in a human and humane context.

So, when do you start exploring all this? My answer over the years for uncomfortable admissions has been that you make them as soon as you start to feel that withholding them is a lie. But I’m going to update that with a nod to self-preservation: Take your time, and pay careful attention to the way a date responds to bad news. If you notice a punitive streak, or if you suspect for any other reason that he’s not a safe place for your secrets, then think carefully; the best course might be to keep the secret and lose the guy.