My boyfriend and I have a fantastic relationship and recently went ring sizing. He has a sexual past, but I do not.

Recently, a young woman I used to see only occasionally became my best friend's sister-in-law.

My boyfriend told me she was one of his past “flings.”

Normally this wouldn't bother me, but he’s quite a bit older than her, which creeps me out. I keep picturing them together.

He then told me the name of every woman he's been with, a list of 30-35 people.

It seems a little extensive, since we're only in our mid-20s.

We run into these people constantly through our work and friendship circles.

How should I react?

Long List

React with self-confidence – he’s ring sizing with you, not any of them. But also respond with a statement of firm boundaries.

He never lied about having a sexual history. But the appearance of this other person (and your obvious discomfort) led him to disclose all.

That’s a strong sign of his concern for your feelings.

Still, the truth comes with new limits in order for you to have total trust.

Most important, he cannot have private friendships, nor meet alone, with any of those women.

If there’s ever a reason he has contact with any of them, he must tell you about it.

This isn’t control. He opened the door to a situation that could otherwise cause insecurity in you. Don’t let that happen.

Stop picturing him with anyone else; he’s your partner and planning the future with you.

My daughter, 50, has two children from a failed marriage. They’re early-20s.

Her partner of 15 years is kind, sweet, and the father of five children. He's never divorced their mother.
He's in his late-50's, smokes heavily and drinks coffee continuously, so his health’s not very good.

If something dire happens to him, my daughter wouldn’t be entitled to his government pension, any retirement packages, or any equity.

She’s stayed home to care for him and her two children. They live in a rental townhouse and haven’t any equity beyond furniture.
She’s overweight and I’m very worried about her health. If something happens to her, he’d expect me or her children to care for her.

Her children are working and going to college. They’re faced with large student debts.
She’s implored him to get a divorce, but he never does.
I think he feels guilty for not having been there for his own children, and wants to leave them whatever meagre inheritance he might have.
Should I speak to him privately or just let them resolve it on their own? She’s threatened to leave him, or that if he gets sick, she won't take care of him..... and he laughs. He knows she’ll be there for him.  But he isn’t there for her.

Worried Mother

Do NOT raise this matter with him. It’s the worst kind of in-law intrusion into a grown man’s private matter.

The person you can talk to is your daughter.

But tread lightly. So far, neither has asked you to care for her and there’s no “dire” situation presently. You’re worrying into the future, but you may turn her off.

Instead, suggest that she take charge of her future and get informed as to whether there are any common-law considerations for her, financially. Or, whether he can leave something for her in his will, despite his being married.

What she learns may strengthen her resolve to insist he make some arrangements to provide for her later.

FEEDBACK Regarding suggestions for women who’ve lived with abusive partners (May 20):

Reader – “I’m a male who experienced a similar situation. I didn't suffer physical harm (I'm 6'2" and 210 lbs.) but I endured years of psychological and physical abuse, and complete sexual neglect.

“My ex suddenly left, secretly. She and her family cleaned out the house, including every picture of our children, without any discussion or consent. While dealing with this shock, I didn't realize what had been taken.

“Based on this experience, I recommend that any woman planning to leave the abuser at some point, somehow take, or have a friend take, digital pictures of the contents of the house and any keepsakes or jewellery.

“Secure the pictures with a trusted friend.

“At the very least, this will enable quantifying the cost of what was taken, and, more importantly, provide it's existence for insurance, divorce negotiation purposes and, if it necessary, theft charges.”