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Hard to Say is This Recording’s weekly advice column. It will appear every Wednesday until the Earth perishes in a fiery blaze, or until North West turns 40. Get no-nonsense answers to all of your most pressing questions by writing to justhardtosay@gmail.com.

Hi,

My daughter has been dating a guy for over six months. He is 24, and unable to hold a steady job of any kind. He never graduated from college, and comes from a troubled family. I have no idea whether he uses drugs or not, but he looks like the kind of person who has at least sampled a few.

My daughter is bright, highly educated and on a great career path in health care. I feel like this guy is a waste of her time and I have told her how I felt. She has informed me that I have misjudged her boyfriend and wants me to get to know the guy. I feel like drawing him any deeper into our family is saying the relationship is acceptable. It's not.

How can I end this thing before it gets more serious?

Kelly K.

Dear Kelly,

Level of education and outward physical appearance is probably not the best way to judge someone, unless that person is Kid Rock. There are plenty of monsters who look like apple pie, and plenty of wonderful people who look like Rob Kardashian. I don't know any, but basic faith in humanity suggests they probably exist.

With that disclaimer out of the way, people do not come to Hard to Say for vague pronouncements about having faith in humanity. I am not your priest.

Sometimes questionable goals require questionable means. Shit-talking your daughter's boyfriend isn't really going to do anything but push her away. If they eventually break up, perhaps she will forgive you in time and subtly incorporate your judgment into her further pursuit of romantic partners. Or the complete opposite could happen and she could begin hiding her relationships from you.

A simple expression of disapproval can work over time, but the problem is that this is not a very intricate dichotomy and you have lost control. If you keep restating your feelings, you become an awful person, which I presume you do not desire. You want to be a good person who is loved by your daughter, and still accomplish your goals.

You need to broaden the complexity of this situation. If you never get to know your daughter's boyfriend well, it is impossible to truly criticize him in the way this situation eventually requires. Your daughter can just suggest you don't have all the information, and she will be right.

The first thing to do is weave praise into criticism. This approach comes across as more realistic, because the world is not a chorus of black and white.

Next, you'll want to establish your own personal relationship with the boyfriend. All of a sudden, your daughter sees that he now has this relationship with another woman, you. Jealousy cannot help but come into play. When a woman sees a man seeking the approval of two women, she subconsciously wonders how many more he is willing to please.

The boyfriend can make so many more mistakes if you get to know him. If he is really not a great match for your daughter, you will be giving yourself ample ammunition, and him ample chance to hang himself.

Then there is also the outside possibility that you will grow to love your new son-in-law. It can happen. I mean it never has for me, but I'm sure it can, I saw it on Lifetime once.

Illustrations by Mia Nguyen.