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. Caitlin Conway says...

    I burst into tears reading this this morning. At the exact moment the ugly crying hit, my 17 month old son started singing “mamamama” from his crib, reminding me that he is still so little and I still have time to sniff his scalp without the guise of shoe laces.

    How are we supposed to survive this?

  2. tiokwanoron says...

    what a bunch of romantic pap. I need advice on a 13 year old who doesn’t care that i hid his new xmas gifted hover board and ping pong paddles because he wont apologize for telling me to shut up, that i took away his computer rights at home for disrespecting his teacher, that his mom does not gives him chores and wont allow me to do so, that he took a fit because one of his male “competitors “in grade 8 got 100% in a math test while he got a measly 97%, that he thinks he has Netflix priority over me who pays for it. Advice on the hard stuff – pleeease.

    • Allison says...

      That’s what I’m looking for too, my son’s a jerk. He’s entitled and lazy, he back chats and pushes the boundaries often. We argue more than anything else. If his siblings get new shoes he wants them too even though he got new clothes the week earlier. If I say he can have three items he wants 5. I ask him to put dishes away he complains and says but I did the washing, not realising his siblings also vacuumed or cleaned the bathroom. I’m at a loss…

  3. Nancy says...

    If you have something difficult to discuss with them, don’t require or expect to meet eyes, or even faces. In fact, if you can talk while both facing forward – say, in a car – that’s best. Otherwise they may feel confronted and shut down.

    • Marcia Beth Roberts says...

      Good advice and true-car rides rock!!=mom of 5 boys

  4. B says...

    Oh my gosh, this made me cry! I feel so sad about my boys growing up, it’s the strangest feeling- like grief in a way. I couldn’t be any happier or prouder in raising boys.

    • Miss M says...

      It is a strange feeling, and it is like grief in a way. I took my younger son shopping for some clothes last night, and in between stores, we sat in the car as he snacked on some chips and drank an iced coffee beverage. I looked at my grown up sized son, my baby I held so snugly, and my heart ached. I have no idea how the years from 12 to 16 happened so damn fast. All I do know is, my sons are nearly adults and I can’t put myself between them and the world anymore.

  5. Jennifer millar says...

    tell them often that you love them, and that nothing they can and will do will stop you from loving them. encourage them to find out who they are, away from parental expectations and peer pressure. I put a ‘positives book’, just a simple writing pad, in the bathroom, toilet, and when they clean their teeth or go to the toilet, spend some time contemplating what was good about today. worked a treat, to make them focus on good stuff that happened, not all the bad stuff. touch them lovingly often, get them used to affection , they won’t (especially girls) look for it on the streets in bad influences if they are loved and cherished at home.

  6. Anne says...

    A wonderfully wise read. I raised two sons and the best advice I can offer is 1) don’t chat at them till they have been fed; 2) always give them a hug at bedtime before you debate when the light should go off, 3) laugh with them, 4) never hug them in public during their teen years but dish up plenty of cuddles at home – the best bridge between adolescence and tormented parents!

  7. Natalie says...

    Thanks so much for that. I have 3 boys the oldest one almost 17. They grow up so fast but they’ll always be my babies.
    Such a lovely read and good to know I’m on the right path.
    Enjoy all the new stories your son will share with you on the next and very exciting chapter of his adventure xx

  8. 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.

    • Oh Beth, this really got me. My boys are 8 and 10, so we have some time, but I’m noticing fewer sticks coming home and my car isn’t as sandy as it used to be. ❤️

    • B says...

      Oh gosh this got me. I hope you can find sunshine today with your sons.

    • Yaz says...

      I have had a similar thought- when was the last reciprocated cuddle? When?? They’re 20 and 16 now… I remember someone saying that sons go to bed one night and wake up someone completely different- it was unimaginable to me. Alas- time proved this to be true with both of them. These young men seem so foreign to me, but when I think of them they’re little and sweet and in my face. My baby boys forever! I mostly respect this new type of reservation in our relationship except when it’s time to say goodbye- then they let me hold them and cover their faces with kisses!

  9. 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.

  10. 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!

    • Marcia Beth Roberts says...

      Am doing. I agree-I love all of it, the friends, the noise, the smelly socks and huge piles of really large shoes in my hallway. My heart does still thrill when my youngest (my boys are now 27, 23, 21, 19, and 14) plops on the bed next to me and the dogs. I love it when he watches his shows on my TV-I am happy to know, to see what interests him. It is ALL good, and going by way too fast ❤

  11. 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.

  12. 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.

  13. 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.

  14. 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.

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

  16. 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!)

  17. 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.

  18. 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.

  19. 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!

  20. Sandy says...

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

  21. anne says...

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

  22. 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!

  23. Jen says...

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

  24. 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.

  25. 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.