I’m a woman, 47, with a successful career. I have an adolescent son who lives with me and spends regular time with his dad.

I've been on my own for years after a too-young first marriage; a nightmare second one, which I fled; and a third which lasted 12 years, produced our son, but ended due to infidelity.

Due to living beyond my means, I pleaded bankruptcy last year.

I’ve been communicating online recently with a man who’s respectful and kind.

I’ve been guarded. We plan to meet soon. There are many things I’m not proud of in my past… but I try to focus on now and the future.

I intend to be honest with him, but should I offer all this information? I sense a real connection there.

To Reveal or Not

The connection you “sense” online is, so far, wishful thinking. It’s still unknown and untested.

Your judgment in the past wasn’t so great, so remember all that you’ve learned by hard experience when you do meet in person. Be honest, but don’t spill everything; it’s too soon and will leave you too vulnerable.

When he asks about your marriages, start with the briefest true response – I was too young, chose badly the next time, but did have a substantial marriage with a man who’s a decent father who unfortunately cheated. Period.

As you date longer, you’ll both have to share more details. What about his relationships, any mistakes?

While still only dating, you’ll have to mention the bankruptcy, because, if it’s a secret that gets exposed, he may wonder if you’re interested in his money.

He’s likely been guarded, too. You’re assuming he’s kind, but you won’t know until you see his behavior with your young son, over time, as well as with you. Proceed slowly.

I'm 27, single mom of a girl, three, seeing a divorced man 47, with an adult son. Our eight-month relationship’s fantastic. Age hasn’t been an issue.

We were coworkers/friends for a year prior to dating. We’ve evolved to being crazy about each other and now he’s hinted about living together.

I’m happy about a possible future together, but eight months’ dating feels too soon, when I have my very young child to consider. We haven’t even said the “L” word yet.

I've gradually allowed him to spend time with us when she’s home (she spends weekends with her father).

They adore each other, but I still worry that it’d be too big a change for her anytime soon. I ended an awful seven years with her father more than 18 months ago.

My boyfriend’s a good father to his son, a good son, brother, and a good friend to his friends. He treats me with respect, is very thoughtful, passionate, funny, intelligent and supportive.
Yet I’ve always had commitment issues.

Now I fear dragging my daughter through any unnecessary pain. Am I unreasonable to think it could be another year or more before I’ll be willing to get that serious?

Your slow process is the right one. You’re absolutely correct and being responsibly cautious to carefully build the relationship between him and your daughter, before seriously discussing living together.

With your weekends free to be with him, you’re not delaying the romance, companionship, or opportunities for intimacy.

You’d have time to learn more about each other, instead of dealing with household and legal issues. Meanwhile, you’re giving your daughter the security that she needs, rather than a fast move to another life, with another man.

FEEDBACK Regarding an inheritance and mistrusting a sibling (Dec. 29):
Reader – “I lived out of town and didn’t see my mother that often. We got along fine, but I’d learned how to draw healthy boundaries for myself.
 “My brother lived across the street from our mother and spent a lot of time with her.

“Her will clearly stated that all was to be divided equally. My brother was executor, took a fee, which is allowed, but he calculated it wrongly, and took extra, saying he’s entitled because he spent more time with Mom.

“It’s strained our relationship. I could use the money as much as he. But I'm especially hurt that he did this though I acknowledge all that he's done for our mother.

“Is the sibling who does more for a parent entitled to more?”

Ellie – The will states what’s legal; fees should be calculated by a legal formula.