Harriette Cole: My new boyfriend has a weird habit when we eat out

DEAR HARRIETTE: My boyfriend and I have been dating for two months. When we go out to dinner, he usually covers our entrees, and he expects me to pay for dessert.

It’s kind of weird because he always makes sure we pay the exact same amount. For example, if we go to Chipotle and he pays, he’ll suggest going to a coffee shop afterward and intentionally orders a lot to even things out.

I wonder why he’s so focused on everything being equal. To be honest, when talking about fairness, he eats and orders significantly more than I do for both the main course and dessert.

— 50/50 Situation

DEAR 50/50 SITUATION: Talk to your boyfriend directly and ask him why he works so hard to make sure that you pay equal amounts on each date.

Tell him you find it strange and unnecessary. Find out what’s at the root of his thinking on this topic. Wouldn’t it be more fun if you two just enjoyed yourselves and were both mindful not to spend too much money?

Rather than using his odd method to split the cost of dates, just divide the check in half if that’s what the two of you have agreed to do.

DEAR HARRIETTE: I’m at odds with my teenage son, and it’s beginning to strain our relationship.

I’ve firmly stood by the belief that my son should earn and purchase his own vehicle rather than having it handed to him on a silver platter, as seems to be the norm among many of his peers. I view this as a crucial lesson in responsibility and independence, and one that will serve him well into adulthood.

However, my son sees it differently.

He’s expressed feelings of resentment and frustration, even going so far as to label me a “bad mom” because of this decision.

According to my son, all of his friends’ parents have purchased cars for them, and he feels I’m treating him unfairly in comparison. He sees it as a reflection of my lack of care and concern for his happiness and well-being.

As a parent, it’s hard to be perceived in such a negative light; I also understand his perspective and the pressure he must feel when faced with the perceived expectations of his peers.

How can I help him recognize the importance of self-sufficiency and independence without sacrificing the bond we share as mother and son?

— On Our Own

DEAR ON OUR OWN: It is hard to parent a child based on your own rules and values when all of his friends follow different rules. That is part of life. This period may stay rocky for a bit, but I think you are doing the right thing in sticking to your values.

You can continue to explain to your son that you firmly believe that he should work for his car.

Yes, it may take longer than makes him comfortable, but in the end, he will be proud of himself for being focused and disciplined.

One option, if it doesn’t feel like too great of a compromise, is to lend your son money for a down payment with a formal plan for him to pay you back. In this way, he can get his car sooner, but he still has to pay for it. You and he can establish a payment plan that he must follow. Importantly, there must be consequences if he reneges on the deal.

Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions to askharriette@harriettecole.com or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.