How do I ask my best friend to be my sperm donor?

Q. Several years ago, my doctor said I was infertile due to a medical condition. I was focused on my career then.

My best friend (male) since college provided support and encouragement.

My next long-term relationship was with a man who stated that he didn’t want kids and was fine with either fostering or adoption if he changed his mind.

He later broke up with me because he wanted biological children.

I was heartbroken and for years after, whenever I disclosed my medical condition, men lost interest in having a relationship with me.

Now, following an unrelated surgery, it was discovered that I’d been misdiagnosed. The surgery remedied what had caused infertility.

I’m 35, own my own home, am financially stable, have a great job with flexible hours, am ready to have a child, but still single.

My specialist has advised IVF (in vitro fertilization) as the best way for me to conceive, but requiring donor sperm.

I’d prefer to use a donation from someone I already know.

I wanted to ask my same best friend to be the sperm donor, but I’m unsure how to approach it.

He’s single and states that he doesn’t want kids. I realize he may change his mind and I don’t want to block any of his future relationships.

I highly respect him, but I want to be clear that I don’t want him to be a “father.”

How do I handle this?

A. Set your priorities:

Do you most importantly want a baby conceived with someone whose background, personality and genetic history are all in your comfort zone?

Or, do you mostly want to raise a child on your own and have full control as the only known parent?

Before that decision, learn all that IVF entails — that it can take time, involving several cycles of tries (and possible disappointments) plus emotional and some physical effects from hormonal changes during the process.

When couples experience this together, the partner’s support is crucial.

However, if your friend agrees to donate his sperm but not be involved as a father, it may be unfair to expect or ask anything more of him.

So be clear not only about what you want, but about what he can or cannot handle in the donor role.

Q. My close friend is 29, male, single and wanting a partner.

He’s good looking, attracts women easily, but things don’t last or progress due to his numerous issues.

Despite being good-hearted and affectionate with close friends, he’s a self- entitled person who takes far more than he gives.

He’s emotionally immature, often swinging from insecure to arrogant.

He’ll periodically blow up with close friends.

Though he doesn’t follow news and is uninformed, he gets defensive and angry when his opinion’s dismissed.

Some of us have encouraged therapy, to no avail.

Recently, he met a single, female acquaintance of mine. She asked for his number, which I gave.

Have I any moral responsibility to warn her?

I know that, one way or another, this won’t end well.

A. Romantic relationships develop in sensitive waters, not on concrete surfaces, so tread delicately.

If they’ve already started something, you could lose two friends by speaking up too directly.

Since his issues do surface, she’ll see for herself where they lead.

To be fair, however, you could occasionally ask how they’re getting along, with some mildly leading questions:

Example: Do you feel comfortable with him? Does he treat you as you wish?