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I have now learned that the only thing more devastating than a failed sleepover is a successful one. Let me explain.

A few weeks ago, Simon got the idea that a sleepover sounded like great fun. He’s spent the night with grandparents aplenty, especially the first week of winter break when Matt and I both had the flu, but he’s never slept over at a friend’s house or had a friend sleep over here.

Then his friend Rhyse’s dad called. He and Rhyse’s mom had out-of-town plans for New Year’s Eve and day, and Rhyse’s older sisters had friends’ houses to go to. Could we take Rhyse? To be honest, the boys didn’t know each other that well. They played soccer together last spring and fall and both go to Brandeis, but they haven’t spent much time together since the fall season ended, and they are in different kindergarten classes.

Still, Bill needed the favor, and Matt and I live a short mile away. We agreed, then got the boys together to play in advance of the big day. They got on fabulously, and after a few short hours both were excited about the sleepover. Then the phone call came: Rhyse had a fever, a trip to the emergency care center indicated it was strep, and the sleepover was called off. Simon wailed.

But we had just left his friend Caroline’s house, and they live even closer to us. So I called her parents, and an alternative New Year’s Eve sleepover was arranged. At dinner time on the 31st, Caroline arrived with a sparkly suit-case and plans to stay up until midnight. The two built a play hut, hunkered down in it, and stayed up hours past their respective bedtimes. I set up our guest bedroom for the two, as the room has a twin daybed and a matching trundle. I finally hauled them upstairs at 11:00, got teeth brushed and pajamas on, read a very long bedtime story about surfing mermaids with hard-to-pronounce names, set up the nightlight, and tried to tuck both into bed.


At which point Caroline insisted she never gets below covers, climbed all over both beds, and then matter-of-factly declared at 11:30 p.m. that she needed her Mommy. This edict was issued with devastating clarity; there was to be no further discussion or negotiation. So her dad came over to collect her while Simon lay in the daybed and sobbed from exhaustion (Caroline is a night owl, but he’s not) and disappointment. As a poor consolation, I offered to sleep in the trundle next to him so that he’d have something like a sleepover experience. It beat a blank, but only just.

Because I felt bad for him and am a glutton for punishment, I called Rhyse’s family the next day to reschedule the original sleepover for the weekend. Friday the boys went roller-skating together, went back to Rhyse’s house to play, and then arrived at our place in time for dinner. Rhyse came with a change of clothes, a pillow, a robe and slippers, and an entire flock of stuffed angry birds. He clearly meant business.

At 9:00 p.m., with a lump in my throat, I hauled the boys upstairs. The trundle was made up with the same sheets from four nights prior, and the entire scene had a discomfiting similarity to it. Pajamas were put on, teeth brushed, and bedtime stories read, though thankfully no epic tales of surfing mermaids. In fact, Simon read one of the bedtime stories himself. I set up the nightlight, gave the same reassuring speech about where to find us if he needed help, and waited for Rhyse to blink once I turned out the light.

It didn’t happen. Instead, we heard about five minutes of chit-chat, then silence from Rhyse and some sniffling and snoring from Simon. Someone awoke at six, thankfully fell back to sleep, and at just after eight both boys came into Matt’s and my room to get the morning started.

Success! Maybe even too much. For when Rhyse’s dad arrived at nearly 11:00 to pick him up, despite or perhaps owing to 24 hours of togetherness, Simon was devastated. Seeing that there was no more play-date to be had, he sat in his little play fort and wept.

Despite or perhaps because of his devastation, I actually felt great. I was sorry he was sad, but delighted that he’s making new friends from school and is hitting these social milestones. A year or so ago, Simon and a friend would have run out of things to do before such a long get-together ended. Now he’s happy to run off with a friend for hours on end and never runs out of things to do. I’ll happily wipe away the tears that result from such progress.


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