46 Things No One Tells You About Parenting a Teenage Boy

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If you think life with an almost-teenage boy is full of surprises, I’m here to tell you the biggest, baddest, and bestest is yet to come. More than big appetites and even bigger messes, parenting a teenage boy is magic and madness — and that’s what makes it so damn good. Bridging those years between boyhood […]

In Defense of the Simple School Dance Ask

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His name was Brian and he was a junior. He had red hair, an ambitious goatee, and he liked me. I suppose I should have been flattered. As a shy freshman, I didn’t get the attention of boys — or upperclassmen — very often. One day after class, Brian approached me and said hello. I muttered […]

The Great Retainer Debate

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Dear Son: These Are the 5 Best Decisions You’ll Ever Make

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My Dear Son, Lately you’ve been hearing a lot about how the decisions you make today affect all your tomorrows. I see you taking it all in. Worrying. Wondering. You mentioned there didn’t seem to be room for mistakes anymore. I tried to assure you mistakes were yours for the making — a rite of […]

13 Things I Learned from My First Week of High School

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Hi everyone, it’s Ryan*. This week I started high school as a freshman. The bad news is that the week was terribly long. The good news is that I learned some things that might come in handy for kids starting high school soon. Take a look:

8 Things Every Parent Should Know Before Their Child Starts Middle School

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In four short days everything will change. My son will walk through the student entrance of his new high school a gawky freshman and emerge a graduating senior in only four short years. I don’t know how we got here so fast. I didn’t intend to speed through this parenting road trip. It feels as […]

62 Thoughts Parents Have at 8th Grade Graduation

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Today I watched my son cross the stage in his 8th grade promotion ceremony. Dressed sharp in a charcoal vest and tie, he took to the field of his new high school seven inches taller and immeasurably wiser than the once-timid kid nearly swallowed whole by 7th grade. Junior high wasn’t easy on any of […]

The Hardest Part of Parenting a Teen Is All the Not Knowing

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Driving home from freshman orientation, my teenage son says nothing. Sprawled out in the passenger seat, bangs covering his eyes, he fidgets with the automatic window. “So, high school … it seems pretty cool, right?” I insist. “I guess,” he shrugs, as he stares out the open window. “High school’s going to be a lot […]

16 Things My Teenage Son Needs to Know About Girls

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If you ask my teenage son what he’s most looking forward to about entering high school next year, he’ll tell you: GIRLS. With a new braces-free smile, fresh undercut, and contact lenses on order, he’s working the accidental heartthrob vibe and loving every minute of it. But before my boy struts his perceived hot stuff […]

85 Completely Rational Thoughts I Had When My Son Traveled Across the Country Without Me

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Coaxing my homebody teen from his comfy boy cave often requires a hard sell. There’s usually some kind of edible bribery involved, and when there isn’t, he’s pretty much clock-watching until we get home. So when my son expressed interest in joining his class trip to the east coast, my husband and I did everything […]