Should I tell my boyfriend that I was engaged to a jerk before I met him?

Awkward Confession

Yes. He’ll be delighted that you’ve now chosen him because he’s a far better man.

If you’re worried that he’ll question your judgment, explain how happy you are to have learned enough from that bad experience to recognize and appreciate a truly great guy.

Withholding this past detail instead, could backfire on you. He’ll find out anyways – through a friend of yours who slips up, gossip, etc. You’d have to lie to cover up for anything that could reveal your past.

His discovery will make it a secret with far greater importance. He’ll wonder if you still have feelings for the guy, or if there’s more you haven’t told him.

Confide now.

I’m mid-20s, dating a wonderful man for six months. He's artistic, funny, geeky like me, makes me feel good about myself, kind and considerate, and handsome to boot!

While I feel comfortable telling him most things about me, I've kept something to myself.

I was previously engaged. Over five years he isolated me from my friends, prevented me from participating in my hobbies, talked down to me, insulted my taste in music/movies/books/clothes, and criticized my appearance.

When I was diagnosed with a life-threatening condition, I didn't even get a get-well card when he learned I was in the hospital.

He lowered my confidence and self-esteem to the point where I felt like I couldn't leave him, even though I was unhappy.
Yet he really only started acting like that (although he was always a bit condescending) after we got engaged.

At the time, I was finishing my first year of college and had only dated a few people, so I ignored my discomfort when he proposed after only six months. I was still in love with him and didn't want him to leave me if I said no.
Four years later, he left me after I finally started insisting he let me see my friends, participate in hobbies, and stop being so mean to me.

Since then, I haven't been in contact with any of his family or friends and, because he met my friends only a couple times, they don't bring him up in conversation either.

Being dumped finally allowed me to realize that the entire relationship had been unhealthy.

My boyfriend knows I was in a relationship with someone for a few years and that it ended with me being dumped, but he doesn't know how unhealthy the relationship was or how "serious" it’d been.

I've worked through some of the issues left over from my ex so I'm not sure he has any reason to suspect what happened before I knew him.

Do I owe him the truth? How much should I tell him? Or should I just keep this to myself and not subject him to hearing about my past?

Better Left Unsaid?

Please see my answer to the first question, which is coincidentally similar.

For the sake of trust, it’s important that no serious surprises occur that shows you withheld a relationship of four years, which affected you greatly.

And it’s important that he keep “getting you” to know that you learned through this experience to stand up for yourself, regain your self-esteem, and feel that you deserve a decent guy who treats you well, as he does.

Confidences bring closeness, which is what intimacy is about beyond sex.

Reader’s Comment - A sincere thank-you for publishing the letter about the grandmother who regularly verbally attacked her grandchildren and their parents.
The letter's situation seems to have started discussions between a few grandparents and parents!
One grandparent has actually started to act differently in dealings with everyone. It seems like a conscious effort and it has already brought positive results among the family and friends.

Maybe seeing your response has made an impact and given the parents and grandparents food for thought. Maybe there’s hope for these families.

Ellie - Too often, I get letters about older relatives who seek attention and power through criticism and judgments. I published this thank you in hopes that many readers, when they recognize troubling situations for others, will pass on any responses they feel may be helpful.

Or, that discussion about a letter moves some people who can relate to the problem described, to think about solutions.