Welcome to How To, Boomer!
Simple tools to help you better understand and communicate with your children and grandchildren in their language.
Pick any tool to open it — your message comes with you. Free, no signup, no card.
What each one is for.
Five small jobs that come up over and over again in cross-generational communication. Pick the one that fits the moment.
- Shame Detector
- Flags shame, guilt, and judgment hiding in a message before you send it.
- Use whenWhen the words feel right but you have a nagging sense they'll land wrong.
- Tone Adjuster
- Rewrites your message with the tone you actually want — empathetic, assertive, lighter, kinder.
- Use whenWhen the message is right but the feeling is off.
- Response Generator
- Drafts a thoughtful reply from scratch, in the tone and style you pick.
- Use whenWhen you've stared at a text for an hour and don't know where to start.
- Translator
- Translates messages between Boomer, Gen X, Millennial, Gen Z, and Gen Alpha.
- Use whenWhen "rizz" or "no cap" stops you mid-scroll.
- Tone Breakdown
- Shows the emotional makeup of any message — empathy, sarcasm, judgment, and more.
- Use whenWhen you want to know what your kid's reply actually meant.
Powered by a mix of modern AI models — we use whichever performs best for each tool. We don't store the messages you paste in.
A whole library to make sense of this stuff
The tools handle the moment. The rest of the site handles the context — where to play this weekend, what your grandkid actually meant, and what to do about it.
- Directory
Pickleball locations
13,600+ courts across 4,694 cities. Find a place to play near you, with hours, directions, and ratings.
Browse the directory → - Blog
Real talk about texting
Plain-spoken essays edited by Holly on the moments that actually come up — how to apologize over text, what to do about a passive-aggressive reply, when to call vs. text.
Read the blog → - Reference
Phrase & tone library
What does "no cap" mean? What's the difference between "lol" and "lmao"? Quick-reference pages for the slang and tone signals you'll actually encounter.
Open the library →
Why families love our app
Stronger relationships
Bridge the generation gap and connect with your loved ones without worry.
Easy to use
No technical expertise needed. If you can send a text, you can use our app.
Family approved
Tested and loved by thousands of families across generations.
What our users say
"Finally, I understand why my grandson keeps saying 'no cap'. This app has helped me communicate better with my grandkids!"
Barbara, 68
"The Shame Detector saved me from posting an embarrassing comment on my daughter's wedding photos. Worth every penny!"
Richard, 72