Motherhood

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.)

  1. Beth says...

    Love going to the playground. One days I realized it had been years since I stood in the playground, pushing swings, finding shoes under sand in the sand box, or catching them at the bottom of a slide. Try as I might, I couldn’t recall the last time, where was it, how long had it been? I was so sad; no one asked me to take them to a playground anymore, and I so wished I had known the last time was real last time.

  2. Celeste Casello says...

    When my son was 6, I was watching him play and blurtered out, “Sometimes I wish I could keep you little forever.” He responded, “Sometimes I wish so too mom. But I want to be big like you….just without the boobs!”
    He is now 9 and is so funny, sentimental, kind and loving. He hugs and kisses me in front of people still and asks for cuddly wuddlies at night and will trade foot massages. I never expected such warmth and love from a boy. I’m glad to hear some of those sweet traits may remain when he’s a teenager. For now, I still watch him sleep while I have the chance and giggle inside that he still leaves the door open when using the bathroom, so he can talk to me. I knew I’d enjoy having a son but it’s so much sweeter than I expected and has softened my heart.

  3. Kelly says...

    My only son is about to turn 32. There are so many times that I think about his teen years- him still living at home, his friends coming over, going to his school events, him making me laugh so hard every day… Those were the best years of my life. Hold on to your sons and appreciate every second you have with them!

  4. Gwen says...

    Beautiful. Mom to three boys, 12, 10 and 22 months.
    One of the most important thing I instill in my boys is to nurture and love each other unconditionally, even when new friendships and partners can strain this connection.
    My sons know I trust them to the core and they know, “I got you” no matter what.

  5. Kirl says...

    It will drive you batty, but let your new teen pick you up. (Imagine a bear hug, at least a few times a week, sometimes less, sometimes more.) He’s testing his strength. It’s exciting to him that he’s turning into a man.
    This will hopefully happen years before he’s calling you, Shorty,
    every. single. day.

  6. Tracey says...

    As I’m reading this my 10.5yo walks past & asks what im reading (probably noting my welling eyes), i answer ‘all the fun things to look forward to having a teenage boy’. Que big hug declaring himself as always my boy.

  7. Erin says...

    I’m currently 20 weeks pregnant with our first, a boy. He’s not even born yet and this is making me simultaneously in love with and already nostalgic for everything that is to come.

  8. My sons are 4 and 4 months and are driving us absolutely bananas and I teared up anyway reading this.

  9. Deni G says...

    These are the very best!
    (Which is really saying something because currently 5 of the 6 tabs open on my internet are cupofjo articles that I love and don’t yet want to close–What do you love about summer, What are your simple pleasures, Does the universe end, What has inspired you lately, and 21 completely subjective rules for raising teenage boys. You guys have the best writers, and also truly the best commenters! This is one of the very few places that I can read the comments without my soul/faith in humanity being destroyed in the process. In fact, I look forward to reading comments here–they’re often as good as the article itself!)

  10. Oh, this might be my favorite post ever! My sons are 7, 3, and 6 months old (and they have 8 and 5 year old sisters!). Right now the days with my kids are sooo long, but I know the years will be short. These little rules are so wonderful and make me look forward to having teens while holding my little ones closer.

  11. My 8 year old son is sitting nearby playing with his sister and I am trying to keep it together after reading #20. Lord, please keep them little for as long as possible because, my heart.

  12. Victoria Foord says...

    Oh dear. I’m not crying, you’re crying! Loved reading this. All true and all helpful. Raising a now 16 year old – whaaattt!!!! How did he turn 16 last week. Its all going so fast now When I say ‘Can you stop calling out Mum for just five minutes’ my husband says “It won’t be long until he won’t be here calling out Mum.” Sob Sob!

  13. Sandy says...

    I have tears in my eyes!! Written so poignantly well!!!

  14. anne says...

    reading this from Paris France
    So true
    Especially N°4 :))

  15. Emilie says...

    Sharing this with my local mom group, makes me weep as I snuggle my 12 week baby boy. Can’t imagine what he and his big brother will be like as teenagers!

  16. Jen says...

    I am also not a mother, but I have a brother and a husband and this is so sweet.

  17. Kait says...

    I am not a mother, but I did just recently move in with my boyfriend. While he has a difficult relationship with his parents (they were not nearly as kind to him as this author was to her sons), I see the way his mother looks at him when we leave a family dinner to go home or she drops us off at our apartment after running errands. I now understand how she feels seeing my boyfriend leave… After reading this article I now have more compassion for her and a checklist of things to keep in mind when I raise my own children one day. Thank you so much.

  18. Graes says...

    Oh! My heart. My sons are 14 and 13 and I know that it will just be a flash before they’re packing up for college. Thank you for the list. I am trying hard not to cry as they are just saying goodnight and my husband is nearby. Reading this while pre-menopausing is not helping with the tears either.