My son, age 24, has engaged in an online conversation for the past four months with a 29-year-old woman who has two children, ages 12 and eight months. She lives in a small town in the United States, two hours from a major city.

My son recently flew there for a week’s stay, to meet her in person.  My son has no permanent job but does have an e-commerce business selling collectible cards.  The woman is a personal support worker.

I am very worried because they have fallen in love and I do not think that my son is ready to make such a commitment.

I think he should get his life together and look for a full -time job and get a career going.

He lives in my condo for free and I pay all the bills.  He has a car and a couple of thousand dollars in the bank.

I think he should get his life together before entertaining this relationship.

What do you think?

Worried Mother

I think that you’re starting to move forward on the wrong foot, regarding the couple’s potential but not yet firm relationship. Best tread lightly.

I say this because nothing affects a young adult’s self-worth, male or female, to feel like a lost soul who thinks they’ve found a better place to land, than still living with their mom and not yet on their own or in a relationship.

I do understand your concern, because so far, your son seems very vulnerable to the idea of starting a new life through this untested relationship, in a different locale, with an older woman with young children and a responsible job (plus an income) who wants a partner... and already feels she loves him after spending just one week together in person.

However, the fact that you keep repeating “I think” this, and “I think” that, is the surest way to have your son fully committed to staying with this woman and only caring about what she thinks.

That approach will push him even further from you, because, if they end up happy together, he’ll resent your ongoing attitude of thinking he should still be following your advice.

Moreover, if their relationship fails, he’ll be back living with you for free, with you again paying all his bills, and he too depressed at how things turned out to “get a career going.” Worse, he’ll openly resent/blame you.

Sorry that this is a grim scenario, but it doesn’t have to happen. You just have to become the wise mother instead of the takeover mother, to create a different conclusion.

Surprise him. Approach the situation differently. Wish him well during this initial “falling in love” period. Be warm and interested in his girlfriend, and chat with her, without making judgements or interrogating her.

She may be a fine woman who genuinely cares for him.

If your son decides to live there, don’t panic. Stay in touch with both of them. Ask about the youngsters.

You’ll learn through these conversations whether meeting her has actually helped him become more responsible about trying to get a job and earn a better living.

After all, he was raised by a very responsible mother. He now just needs to learn how to be responsible for himself, and become a full partner in his new relationship.

My niece, 22, is too pretty for her own good. She grew up pampered by everyone, and always had a boyfriend since age 14.

She’s relied on them buying her expensive gifts, and never worked at a job for more than a month.

Now, her latest boyfriend is fed up, and she’s couch-surfing, crying that she “did everything for him.”

She’s too ashamed to tell her parents she’s been dumped. But I’m not interested in supporting her. What should I tell her?

Self-Centered Niece

How interesting: Two entirely unrelated but very similar problems from readers on one day!

You can provide a one-time chance at increasing her self-worth: Help her enlist in a proven job-seeking course through career counselling. It’s a gift that can keep on giving self-respect, too.

It only requires you to take a real interest in the course and in her as a person, finding that she can achieve growing independence.