Cup of Jo

21 Completely Subjective Rules for Raising Teenage Boys

Hannah Mas

Catherine Newman has two children, Ben and Birdy. This fall, Ben left the nest for college, so we thought it was the perfect time to hit her up for advice. Sometimes I worry about losing the connection with my funny, vulnerable little boys as they get older, and, when I mentioned this to Catherine, she replied: “It will be just the way it is now, only they’ll be sweet-hearted young men, and you will feel very short.” Here, she shares 21 completely subjective rules for raising teenage boys…


I hadn’t realized that raising a teenaged boy would involve all the tenderness of a violin spilling out a persistent heartbreaking melody in the background — and also, of course, all the crash-banging of a drum set. But it’s both things all the time. And, come to think of it, that’s true of raising a teenage girl, too, a scenario to which most of these rules also apply. The main rule, which you already know, is to love these big kids fiercely and excessively.

1. Teach them to respect women. Not in the pretty-object-on-a-pedestal way of things and art; in the way of real, human equals with a right to their self-determination, intelligence and space on the subway.

2. Enjoy the same funny conversations you’ve always had, especially while walking in the woods or cuddled on the couch. “If it were for charity, how many pieces of buttered rye toast do you think you could eat?” he might ask, and then look aghast when you say ten. “What? Twenty at least.”

3. Love them for sleeping late. The only other option is to not love them for sleeping late, since the sleeping late is itself a given. They’re creating many inches of new human flesh a day, and it’s exhausting! (Remember pregnancy?) When they stagger out at 2 p.m. with their man-sized arms and legs and their sleep-creased baby faces, you can just say, “Did you have a good sleep, my love?” instead of “Good AFTERNOON,” like all of our own passive-aggressive parents did. And you might be treated to a languid smile, a comfortable stretch, and the simple pleasure of the words, “I did.”

4. Be kind to your child, even if it seems like he doesn’t notice or care. He does. Treat him to donuts, to barbecue, to a big smile, a cup of tea, the benefit of the doubt. When he lies down in your bed to be near you and the cats, you can go ahead and keep reading your book — the cats are purring enough for all of you — but it’s okay to brim with joy.

5. Prepare for cranky questions to emanate from the open fridge: “Is the ham all gone?” “Wasn’t there leftover steak?” Answer with your sunny good nature. “It is!” “You ate it!” Remind your son that he is welcome to restock the fridge.

6. Familiarize yourself with the expression “second dinner,” and buy lots of Trader Joe’s frozen entrees for hungry nighttime foragers.

7. Enjoy the beautiful, gentle, funny boy who says deadpan things like, “Same,” to make you laugh after you muse aloud that perimenopause is killing you.

8. Be trustworthy. Be respectful. If they turn to you with something bad or hard, the first message should be, “I’m so glad you told me.” The second message should be, “How can I help?”

9. Whether they’re dating boys or girls or nobody, talk to them about consent — watch the British PSA video “Tea and Consent” together as a jumping-off point — and then, if they’re having sex, give them space and room for it. Because, despite whatever fun you may have had behind the bleachers or in somebody’s parked car, hurried sex tends to be bad and potentially unsafe sex.

10. Assuming you actually want your son to join you, whatever it is you’re doing, the answer to the question, “Is it okay if my friends come with us?” is always yes. Also, because you will remember when he was too shy to invite people over.

11. Relatedly, keep around plenty of games and musical instruments (Catan, Kan Jam, a couple of ukuleles) to give the kids lots of fun things to fill their time with besides the kinds of fun things that you might be less excited about.

12. Preserve your teenager’s dignity. If products like acne wash or deodorant seem called for, these things can be unobtrusively purchased and encouragingly left out. Relatedly, the things you used to do with the bathroom door open? Shaving your leg with a foot in the sink, yanking up your tights, tweezing your beard hairs? Go ahead and close the door. Or prepare to witness comedic horror-movie type horror when your son passes by on his way to the cold cuts.

13. For everybody’s sake, knock before entering. In fact, maybe even, like, bang a gong outside the door before you get near enough to knock.

14. Take a picture of the heap of gigantic shoes by your front door because one day they will not be there and you will want to tearfully reminisce.

15. Teach them the important life skills: How to send a thank-you note. How to listen and ask questions. How to walk into a kitchen and say, “Put me to work.” How to call their representatives about an important issue. How to clean a bathroom, do a load of laundry, scramble an egg. How to sit patiently on the sofa between their two grandparents with their two new iPhones, nodding slowly and saying, “Here, let me show you,” when the grandparents are convinced the Google has gone missing.

16. Substance wise, consider moderation over prohibition. That said, if you make one rule, let it be this: “Don’t ever try meth, crack cocaine, or heroin. Ever, ever, ever.” Explain the way these drugs permanently mess up your dopamine receptors (if you need to learn about that first yourself, do).

17. Pick your battles. Personal style is a pretty low-stakes form of self-actualization; if the way they wear their hair or jeans (hello, bum crack!) is not your very favorite, complain about it to a friend.

18. One night it will be late and they will be out with the car and you will hear the far-off sirens of emergency vehicles. Be still your beating heart.

19. Pretend you’re just tying your shoe so they won’t notice you leaning in to sniff the still-intoxicating smell of their scalp.

20. Lying in bed at night, scanning around to check for various dangers and unhappinesses, you will mentally find your son safe in his bed, in his room, in your house. And you will remember to be so, so grateful. Because one day you will buy him a memory foam mattress topper and a set of twin XL sheets and, poof, he will leave behind a heartbreaking boy-shaped hole.

21. Wherever they go, physically or emotionally, understand that they’ll come back to you. And when they do, go ahead and fling your mama arms — your mama heart! — wide open. Wide, wide open.

What would you add?


Catherine Newman is the author of, most recently, Catastrophic Happiness and One Mixed-up Night, a YA novel. You can find her at Ben and Birdy.

P.S. Five ways to teach kids about consent, and 21 completely subjective rules for raising teenage girls.

(Photo by Hannah Henderson.)