Do I have to tell her about my past

Good morning. I am in Los Angeles visiting family. That's why today's letter was posted at a crazy hour. I'm posting letters before bed this week so I don't have to get up early.

I hear we got some snow at home. I'll be thinking of you in sunny Solvang today as I drink wine and eat Dutch pastries (yes, I'm rubbing it in).

Hi Meredith,

For the past few months, I've been in a wonderful relationship with an equally wonderful girl. It has been the most natural, comfortable relationship I've ever experience. Both of us feel at home with each other and I really couldn't be happier with the way things are going.

But if I didn't have a predicament, I wouldn't be writing to you. I was in a long-term relationship that lasted several years and ended over a year and a half ago. While I was with her, I cheated on her several times. I recognize what a despicable thing this is to do to someone, and to the best of my knowledge, she has no idea about my misdeeds. I really do feel horribly about what I did, and I realize that even wanting to cheat was a sign that I needed to examine or possibly end that relationship.

Now that I'm in a new relationship, am I under any obligation to disclose my past indiscretions to my current girlfriend? I don't want to hide anything from her about who I am and what I've done (and we both certainly know about at least some of each other's less-proud moments), but I'm afraid that for so many people this is an issue that is simply never acceptable. I feel dishonest for not revealing my history, but I don't want to ruin something this great for no reason. What should I do?

– Do I Tell?, Somerville

I'd tell her, DIT, but only when it feels organic. Don't make it a big, nasty confession. A guilty sit-down implies that your bad behavior is going to continue and that cheating is something you do in all relationships. Your disclosure doesn't have to be a warning.

When you do tell her about the cheats, give her some context. Let her ask questions. Tell her what you told us -- that you cheated because you were sabotaging a bad relationship. You learned a lesson.
Many people do awful things at the end of relationships. We know that from Love Letters, right? They check each other's e-mails, they say mean things about each other's family members, and they behave like children, in general. I'm sure this woman has her own list of misdeeds from her past, including some you don't already know about.

Don't alarm her with a big dose of dramatic news unless you feel it's relevant to your relationship.
And if this is really about wanting forgiveness from your ex, let it go. Allow everyone (including yourself) to move on.

Readers? Am I wrong? If you used to be a cheater, do you have to tell your new significant other? And if so, how? Does the letter writer's anxiety mean that he wants to apologize to his ex? Should he? Discuss.

– Meredith