Dadvice Weekly #34 / Roadtrips & Grief
Traveling with a five-year-old to a funeral
I’m writing this from a hotel room in Kansas. Bennett, my five-year-old, is asleep next to me after four days of funeral service, family dinners, and a whole lot of “Dad, who’s that again?” Because of foster care logistics, the rest of the family stayed back in Colorado Springs. So it has been just the two of us, for the first time ever, surrounded by my side of the family. Watching him represent the next generation of our family while I was also saying goodbye to grandma has been a beautiful experience. This week’s issue is what I learned. –KC
Plan “Roadside Oddity” Pit Stops / Look for Fun
Eight hours is a long drive with a five-year-old, so I asked ai to look for “roadside oddities” along our route. Every two to two and a half hours or so we had a destination, something absurd and specific that Bennett could look forward to. Between Colorado Springs and Kansas City, we stopped at the world’s largest easel (a Van Gogh replica) and the world’s largest hand-painted egg. On the way back, we’re hitting the world’s largest belt buckle. It gives him a mental reset between stretches of highway, and it makes eight hours feel a lot more managable.
Get Your Kid a Camera
Bennett received a small kids’ digital camera before we left, and we challenged him to take good pictures to show mom and the siblings when we get back. We had to have multiple conversations about privacy and not pointing it at people at inappropriate moments, but looking through his photos and videos afterward was really special. He photographed great-aunts he’d never met, the hotel breakfast buffet, the backseat of the car. Seeing a roadtrip and family funeral through a five-year-old’s lens, what he chose to document and what he ignored entirely, was really cool, and I’m so glad we have those to look through together.
Never Underestimate the Snack (and Underwear) Situation
I packed light on snacks, which I will not do again. The rule I’ve now adopted: if a five-year-old mentions hunger or a bathroom, you have approximately thirty seconds before it becomes a full situation. There is no “hold on” or “we’ll stop in twenty minutes.” The world stops. Everything else is secondary. I don’t say this to scare you, I say it because I thought I knew and I was wrong. A small cooler with real food and a few of his favorites would have prevented at least two tense stretches of I-70. Lesson learned.
Embrace the Kid Buffer
Here is something no one tells you about bringing a young child to a funeral: they are genuinely useful. Not so much in a task-oriented way, but in the way that a five-year-old has no filter and absolutely no ability to read a room, which, in the middle of grief, is exactly what a group of adults needs. When the service ended and Bennett said loudly, to our entire row, ”Finally!”, everyone laughed with relief. You can’t manufacture that, and you also can’t control it, which means at some point you have to make peace with the fact that a squirming kid at a church funeral is going to do what he’s going to do. Embracing it instead of fighting it is very rewarding.
Let Them See You Grieve
There have been lots of tears from lots of people on this trip, and Bennett’s seen them. After the funeral he asked me if I was sad, and I told him yes, that I loved my grandma and I was going to miss her. He patted my arm. What I didn’t expect was watching him, over four days, learn to match the emotional temperature of the room. He got quieter during the hard moments. He hugged people without being told to. He told my aunt he was sorry about her mom. I don’t think any of that happens if I’m shielding him from the uncomfortable parts. Grief is good, emotions are good. Let them see the whole thing.
Dadvice Weekly is Kyle and Skyler—two friends in their thirties, living in Colorado, settling into fatherhood and trying to stay sane. Every Tuesday we share what’s working in our homes: gear we use, routines we’ve tested, ideas we’re trying. It could be a recipe, a product that solved a problem, or just what we’re thinking about as dads.
If you have a tip, tried something we mentioned, or just want to say hi, reply to this email or message us on Substack. We read everything, and we’re always looking for what works. Glad you’re here.




