Built for one mom. Now built for yours.
How To, Boomer! is a small, family-run project from a mother and her son. We make simple communication tools and a national pickleball directory — both designed to help people across generations connect a little more easily.
The generation gap is mostly a translation problem.
A lot of the friction between parents, kids, and grandkids isn't about love or care — it's about words landing the wrong way. A text meant as concern reads as judgment. A reply meant to be light reads as dismissive. Decades of shared experience can get lost in a single ambiguous emoji.
We built How To, Boomer! after a string of those misfires in our own family. The tools here are the ones we wished existed: something that could check a message before we sent it, suggest a kinder version, or just explain what "rizz" is supposed to mean.
A mother and a son.
Holly
Holly is the reason this exists. She's the one who kept running into the everyday text-message moments that needed better answers, and she directs every blog post on the site — choosing the topics, framing the questions, and reviewing the drafts before they publish. AI tools do the prose drafting; Holly does the editorial work that decides what gets said.
Kyle
Kyle has been writing software for 10+ years and spends most of it now trying to keep up with Holly's ideas. He builds the tools, the directories, and the parts of the site that move.
Editorially directed, AI-assisted, human-reviewed.
We want to be honest about how the blog is made: Holly chooses every topic — the everyday text-message moments she keeps running into with her own family and friends — and frames the angle. AI tools help draft the prose. Holly reviews each post before it publishes. Think of her as the editorial director rather than the typist.
The communication tools (Tone Analyzer, Tone Adjuster, Shame Detector, Response Generator, Translator) use a mix of modern AI models — whichever one performs best for the task. They run on demand each time you click a button. We don't store the text you paste in.
Our directories are built from curated datasets — cleaned and verified before anything goes live. Pickleball came first (13,600+ US locations), with more places worth knowing about on the way: parks, hikes, RV resorts, and other spots that are actually built for the people we built this site for.
Tell us what's working.
Found a court missing from the directory? A tool result that didn't land? A boomer-perspective topic you wish we'd cover? We read every message.
[email protected] →