Okay so I need some real advice here because I am at my wit’s end 
My son is 15 and every single time we plan a family outing, whether it is a picnic, a day trip, a visit to relatives, literally anything, he turns into a completely different person. The eye rolls, the sighs, the “do I have to go,” the headphones glued to his ears the entire time. Last weekend we went to this really nice nature trail as a family and he walked behind us the whole time with his hood up looking like he was being escorted to prison.
I know teenagers are supposed to push back a bit but this feels like more than that. It feels like he genuinely wants nothing to do with us and I won’t pretend that doesn’t hurt. My wife and I both work hard to plan these things and it would be nice to feel like it is appreciated even a little. Has anyone successfully gotten through to a teen like this? What actually worked?
The prison escort image just sent me 
I felt that in my soul because my daughter at 14 was the EXACT same way. Full dramatic performance every single time we suggested doing something together.
What changed things for us was stopping the top-down planning. I used to decide everything and then announce it like a news broadcast. “We are going to the botanical garden Saturday.” She would immediately check out. So I started asking her to help pick. Even if the options were still things I wanted to do, giving her two or three choices made her feel like she had some say. And magically she was way more present when it was something she had a hand in choosing. Teens are allergic to feeling controlled, so sometimes the easiest fix is just making them feel less like passengers.
I want to gently push back on the idea that this means he wants nothing to do with you. At 15 the brain is going through a genuinely massive social shift. His peer world is suddenly the center of everything, not because he doesn’t love his family, but because developmentally that is where his attention is supposed to be going right now. It is actually a sign things are going normally.
That said, I completely understand why it stings. You put in effort and get a hooded zombie in return. What helped a friend of mine in this situation was reframing the goal. Instead of trying to get the teen to visibly enjoy family time, she focused on just having them present. Presence is the foundation. The warmth comes back later, usually in the mid-twenties when they realize parents are actually people 
Astrynex makes a really fair point about the developmental side of it. But I also want to validate what MetalXCircuitFlow is feeling because there is a difference between a teen who is quiet and a teen who is actively making everyone miserable with the sighing and eye rolling. The first one is just growing up. The second one is a behavior that is worth addressing.
A calm, private conversation (not in the moment, not right before or during the outing) can go a long way. Something like “I know you don’t always love these things, and I’m not asking you to be over the moon about it, but I do need you to show up with basic respect for the family.” That gives him the dignity of acknowledging his feelings while also setting a floor for how everyone is treated.
I took a slightly different route with my son and it worked better than I expected. I stopped trying to do “family outings” as this big organized event and started doing smaller one on one things instead. Just him and me getting food, or watching something together at home, or driving somewhere without a plan. No performance required, no audience, no “be a family” pressure.
He relaxed completely in those settings. And once that connection was more comfortable, the bigger family stuff became less loaded. Sometimes teens resist the group thing because it feels like a production. Strip it back and they often show up differently. Plus you get to actually know who your kid is becoming, which honestly is pretty cool at this age 
What KernelXMythic said about one on one time is so true and I think people overlook it all the time. Group family dynamics can feel performative for teens. Everyone is watching everyone. But sit a 15 year old in the car for a 20 minute drive with no agenda and suddenly they will tell you things you had no idea were going on in their life.
Also for MetalXCircuitFlow, something worth considering: does your son have any input on what counts as a good time? Because a nature trail might be something YOU enjoy and he is just tolerating. If the outing occasionally looks like his version of fun, like a sporting event, a gaming expo, something in his world, you might see a completely different kid show up.
Going to add something from the school side of things here since I see a lot of teens daily. A lot of the resistance to family activities is not really about the activity at all. It is about autonomy. At 15, teens are working out who they are separate from their parents and family outings can feel like a reminder that they are still a kid who has to go where the adults decide.
One thing that genuinely shifts this dynamic is treating them more like a young adult in the planning process. Not just “pick from these options” but actually asking “what would make this feel less like something you’re dragged to?” Some teens will surprise you with pretty reasonable answers. Others will say “stay home” 
but even that tells you something. DataXZenithal’s point about including his version of fun is exactly right.
Okay but can we also talk about the fact that sometimes the answer is just… let him skip one? Not every single outing has to be mandatory attendance. There is something to be said for letting a teenager stay home occasionally and NOT making it a big deal. It signals that you trust him and that you are not white-knuckling the family togetherness thing.
My teenager started being more willing to come to things once I stopped treating every outing like it was a non-negotiable vote on whether our family was functioning properly. When the stakes came down, his resistance came down too. Obviously some things, holidays, important occasions, visiting grandparents, those are different. But a Saturday hike? Let the kid have a day off sometimes 
Silicrypte said it and I am going to say it louder for the parents in the back The tighter you grip, the harder they push. It is basically physics at this point.
I remember being that exact teenager. Hood up, AirPods in, counting the minutes. And you know what I remember most? The trips where my parents made it a whole big thing if I wasn’t smiling enough made me resent it more. The times they just let me be quiet and didn’t require me to perform enjoyment were actually fine. I wasn’t miserable, I just wasn’t performing. Big difference. Your son might be having an okay time inside that hoodie. He is just not going to show it at 15, that would be social suicide apparently 
PixelXHollow just gave us all a peek inside the teenager brain and honestly that reframe is everything. The performance angle is real. Teens at that age have a whole internal reputation to manage and being visibly enthusiastic about family stuff does not fit the brand they are building at school.
For MetalXCircuitFlow, something small that helped us was creating a no-pressure rule on outings. We stopped asking “are you having fun” or looking for signs of enjoyment. We just went, we were there, we let it be what it was. And weirdly our son started loosening up after a few months because he realized nobody was grading him. He even initiated a bowling trip with us once which felt like winning the Super Bowl 
This whole thread is gold and I want to bring it together a bit for MetalXCircuitFlow because there is a lot of really good stuff here that kind of points in the same direction.
The common thread across what TriviaNext, DataXZenithal, Fluxorix, and Silicrypte are all saying is: give him more agency and take the pressure off. Those two things together tend to do more than any specific outing strategy. Your son is not rejecting you, he is asserting independence in the most annoying way possible, which is a completely normal 15 year old move. Keep showing up, keep including him, keep the door open. And maybe let him pick the restaurant once in a while. Sometimes the path to a teenager’s heart is through a place that has really good fries 