When my boys were little, I had one on one time with them all day long. I chose to be a “stay at home” mom and our days were packed with play and parks, and classes, and snacks and naps and more play. It was non-stop crazy and super tiring, but the best of days as well. And then they went off to school.

Now I see them for a bustling hour or two in the morning and from 4-8ish o’ clock each evening. Those 4 hours are packed with homework, activities, dinner, more homework, and bedtime stuff.
Not the most “quality” of time with each other to say the least.

There’s barely time now to look each other square in the eyes let alone have those deep, soulful, “tell me everything you’re thinking” (and I’ll actually listen), kinda moments.

It’s for this reason I started up an annual tradition with my first-born boy Maxwell whose now 15. Back when he was a round-faced second grader I decided we needed a yearly overnight adventure…just us. A sleepover in the city (we’re a 25 minute train ride from Chicago), including a fun show of some sort, a “fancy” dinner, and a stay at a fun downtown hotel.

That first year I took him to see The Nutcracker because I knew that ballet would at some point become a tough sell.

We packed our bags, got all dressed up, and took on the city together. He loved the show, the very grown-up dinner, jumping on the fancy hotel beds, ordering room service, and wearing the way-to-big fluffy white robes. And I loved having my little dude all to myself, looking him deeply in the eyes, and listening to everything he was thinking.

That one little overnight was so blissful and fun that we’ve replicated it every year since.
Together we’ve experienced Wicked, A Christmas Carol, American Idiot, and this year, Les Miserables. Every time Maxwell agrees to hang out with “just me” for a night, I demurely smirk on the outside and do a full-blown hammer dance on the inside.

This year, with Max being a big ol’ freshman, I held my breath when asking if he was still “into” our little holiday tradition. His enthusiastic “Are you kidding? I wouldn’t miss it” reply was better than any gift I’ll get under that illuminated tree in the corner of my living room.

Establishing the tradition of a one on one get-away with each kid once a year before they become tweens and teens was one of the better parenting decisions I’ve ever made. It doesn’t have to be a fancy holiday-fueled deal, or set at an expensive hotel. It just needs to be thoughtfully planned and impervious to busy schedules. You’ll thank me later.

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