OP here, and it's interesting to see such a wide range of responses. I think we'll give it a try and see how it goes.

Have you ever tried Outschool classes? They’re online, so it’s not exactly socializing, but it’s a very portable way to fill some hours. There’s everything from one-off classes to summer-long series, on every topic you can imagine. Some of the popular classes fill up early, but with advance coordination you could sign up along with a friend so he has an active way to stay in contact with his friends while you’re gone.

Certainly not. My kids would hate that.

Awkward. This is a terrible idea and out of a bad wimpy kid movie. You are that parent if you do this.

18:06 here and I just remembered that one of most memorable times in my life was when my aunt and uncle took me out of school (I want to say in 7th) for a three-week trip around the US and Canada.

They had a company that made inferred thermometers when it was a newer thing, and were visiting clients (which were like, breweries or other big plants, graineries) so it wasn't like we were going to fancy hotels or anything. I think we stayed with his brother and wife in one city.

I didn't meet any kids on that trip. I didn't want to go on the trip (was worried I'd miss out at school, or my friends would dissappear) but really, it was a great experience and I don't think it mattered at all that I was a kid and not meeting other kids. I think it just would have been awkward.

Anonymous wrote:This is super kid specific.

My 12 year old son would straight up hitchhike back home if I forced him to meet stranger tweens during a family road trip vacation. He would absolutely barrel roll out of the car at 60 mph and refuse to speak to us for months.

LMAO! Agree it's kid-specific. If OP will be traveling for ten days, the kid will be fine. If OP will be traveling for two months, that'll get old for the kid.

Anonymous wrote:During the pandemic? No.

And as a teen I think I would have found it awkward

Ps. I would have preferred to sit and converse with the grownups rather than be forced to socialize with teens I didn’t know

During the pandemic? No.

And as a teen I think I would have found it awkward

I would hate to meet strangers along the way & I'm a grown-up!

No way!

How long is the road trip? It might work if whoever you are visiting invites a family over for dinner. Then the kids can hang out together if they hit it off, but they can also hang out with the adults if they don’t hit it off. Maybe they could also watch a movie together while the adults chat after dinner.

I can't imagine tweens (or teens) doing well in this situation.

I think it would be great for your kid to hang out with adults. Our society is so stratefied these days, the kids hang out with the kids and the adults with the adults, and kids don't often get to sit in on adult conversations anymore. It's good for the kids!

It's especially good for boys to hang out with a group of older men like that. It's like overhearing how adult men (married, or dads, or adult working men) operate, and what their concerns are.

I'd say this is worth a try if your friends have friends whose kids they know pretty well and so it doesn't seem contrived for them to include the kids in some low-key outdoor activity. So, less like a fix-up and more like a hangout. Does that make sense at all? I'm answering from my perspective as a middle-school teacher, but also because 15 years ago our family went on a long road trip up the California coast and arranged to do a hike with friends of friends who, like us, had a 12 y.o.son. My husband and I had met the parents years before at the wedding of our mutual friends, but we hadn't seen them since then. Our sons hit it off and our families ended up taking other vacations together. Ten years later the guys both got into the same law school and decided to room together. In August, their son will be in our son's wedding. You never know when you might make a friend for life. Have a good trip, OP!

This is super kid specific.

My 12 year old son would straight up hitchhike back home if I forced him to meet stranger tweens during a family road trip vacation. He would absolutely barrel roll out of the car at 60 mph and refuse to speak to us for months.

We're heading on a lengthy road trip with our tween. None of the people we know and have arranged to meet up with on the trip have children. Does it make sense to check if they can introduce us to other families with tweens with whom he might be compatible, so he doesn't feel like the only kid around all the time, and doesn't want to spend most of the time with a nose in a book or playing games and socializing with friends via a screen. Or would that just be awkward at these ages? He's friendly but slightly introverted, and tends to be reserved until he gets to know someone. I'm thinking we could suggest going hiking or doing other low-key outdoor activities that parents, children, and our childless friends might all enjoy.