Dear Amy: My 24-year-old gorgeous, loving and generous daughter dresses (quite honestly) like a messy frump!

This wouldn’t be that big of an issue, but she does not have a boyfriend and is extremely lonely.

So far, she has had nothing beyond first or second dates.

Fortunately, we run a trade school and have about 50 eligible men coming through our school each year, but she refuses to keep her hair brushed or wear stylish clothes (even though I’ve taken her shopping for numerous professional outfits).

It’s not that she’s depressed or doesn’t know any better. Amy, she thinks she looks “just fine” and I’m a “very judgmental mom.”

Her dad and I want someone to love her just the way she is, but first impressions matter, and she makes a poor one.

I have tried to be tactful, matter-of-fact, and even rude.

I have given her clothes, brushes, and hair straighteners. We are almost positive that the reason she has not met the potential “one” yet is because she comes across as a frump.

I assume that you will tell me to stay out of it, but it’s hard to do that when I know that if she just tried to jazz up her initial impression a wee bit it would make all the difference in the world.

— Mom of fantastic frump

Dear Mom: Wow, mom. Your question reads like something pulled from the wayback machine when mothers encouraged, coached or bullied their daughters on how to catch a man. (In the movie version of this, Joan Crawford might play you.)

Your daughter might be lonely, but maybe she doesn’t want to date men. Or she might want to date men but perhaps NOT the ones who pass through your trade school. At 24, with full access to options and information, she should be free to make her own choices about how she wants to look and dress.

You’ve already deployed the nuclear option by being flat-out rude about her looks. I wish you would imagine the impact of this on her. Of course, the pressure you are exerting is not helping her. In fact, it is hurting her. Your description of her comportment and dress is of someone who is trying to be invisible.

If you can’t love your own daughter as she is, then how will she gain the confidence to find someone else who loves her as she is?

Ideally, home and family should be a safe harbor from the slings and arrows of the rest of the world. Or, as my mother used to say, “If you can’t say something nice, don’t say anything at all.” (Yes, her silence sometimes spoke volumes.)

Your daughter should seek gainful and fulfilling employment, concentrate on her professional and personal development, work on her peer-friendships, and move away from your orbit. These are the only life skills you should be passing along.

Dear Amy: I have a close cousin. We practically grew up together. We’ve always gotten along very well.

For the last several years, we have said that we wanted to go on a vacation together. Well, we finally did it! Amy, it was kind of a nightmare.

“Clara” was overbearing, bossy, wanted to sleep late and party later. She decided to basically chain smoke (I didn’t know she smoked), was rude to staff, and very messy.

I was hoping to go on walks together, do some bird-watching, and just basically enjoy each other’s company. Instead, I felt trapped with this mini-monster.

She is making noises about wanting to do this again. What should I say?

— Recovering

Dear Recovering: Some people who are otherwise compatible just shouldn’t travel together. “Clara” sounds like someone who basically goes feral the minute she crosses the county line. I know people like this, and I have been through these feral stages, myself.

When you saw the direction things were headed with her, you should have carried on with your own plans hiking, bird-watching, and basically having some of the experiences you wanted to have.

You should be honest with her: “I love spending time with you, but we travel really differently. I’m going to pass on another vacation.”

Dear Amy: “Suspicious Daughter” was upset because her older dad was in a relationship with a much younger woman. Thank you for basically telling her to mind her own business!

— Older and Wiser

Dear Wiser: It can be very hard for family members to let go. An abundance of concern can turn into an abundance of control.


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Contact Amy Dickinson at: askamy@amydickinson.com.