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Dear Amy: My boyfriend of more than five years recently was approached by a woman he has had a working relationship with for about six months to donate sperm for her to have a child.

She has offered him fair financial compensation, and has assured him that he will not have to be a part of this child’s life if he does not want to be.

I know this is a difficult situation for him and I want to be there for him if he does agree, but I feel scared of all of the things that could happen.

My own insecurities may cloud my judgment.

He is going to see a lawyer, so I feel comfortable with the legal issues; but the emotional aspect of this worries me.

We are both in our early 30s. We are not ready to start a family, nor are we even sure if we want to do so.

He has a great heart, and I cannot imagine he would be happy having no relationship with a child.

I would feel totally different if it were an anonymous donation, and not someone he needs to see on a regular basis.

How can I be the supportive girlfriend, while facing my own insecurities about this new chapter of his life that I am not a part of?

— Dreading in Denver

Dear Dreading: There are insecurities, but then there also are very real, very important and very challenging questions raised by this situation, and you should be absolutely honest and forthright.

This plan presents an emotional, legal and ethical minefield.

Even if these two started out with a signed, airtight contract and money exchanged, babies have a way of subverting even the best-laid plans.

For instance, what if your boyfriend felt the mother wasn’t a very good parent? What if the mother wanted your boyfriend and the child to have a relationship and he didn’t want to? Or what if she denied a relationship that he wanted to have? What if the mother wanted to hook up with a motorcycle gang, or enter the toddler in beauty pageants, or have the whole thing filmed for a reality show?

These two know each other professionally. How will your boyfriend feel to see baby pictures on the other person’s desk? Will she be open or discreet about this arrangement? Will he? Will you?

This choice affects you profoundly. Everybody involved in this situation should seek professional legal, ethical and emotional guidance.

Dear Amy: I think you missed a big red flag in the letter written by “Conflicted,” who said her husband disliked her best friend.

This husband sounds controlling, and this situation sounds like the beginning of what could become an abusive marriage, starting with attempts to isolate Conflicted from her support network.

Hacking into her email is a dangerous sign that this husband may think that he should have complete domain over his wife.

Why shouldn’t Conflicted talk to her best friend about her marriage? Sure, maybe she shouldn’t be reporting personal details like the size of her husband’s assets, but it sounds like Conflicted was seeking support from her best friend about how to navigate her new marriage — something she ought to keep right on doing, given the bully it seems she may be married to.

— Concerned About Conflicted

Dear Concerned: Many readers echoed your concerns. Though I did say this husband’s behavior was wrong, in my answer I focused on some of the wife’s choices that I felt contributed to the conflict between these two people in her life.

Thank you for waving this “red flag.”

Dear Amy: Your advice to “Dog Tired” was way off. As this gentleman explained, he is on the verge of moving in with his girlfriend, but he is concerned about the “custody arrangement” of two dogs she shares with her ex-husband.

You suggested he “embrace the canine relationship” when it was crystal clear he doesn’t like dogs.

My advice to him would be to tell her, “It’s me or the dogs” and discover how she really feels about him.

— Also Dog Tired

Dear Dog: When you say, “It’s me or the dogs” to a dog lover, you will find out exactly where you stand.

In the doghouse, most likely.