Friendship Boundaries | Ask Uncle Gary

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Eleven Months Later

Altadena, CA. Nearly a year after the Eaton Fire carved its way through the foothills, the town is still living in its shadow. Eleven months sounds like enough time for life to snap back into place, but for many families, the calendar doesn’t match reality. People are still scattered across borrowed bedrooms, spare couches, and motel rooms that were never meant to be home. Entire neighborhoods feel like they’re holding their breath.

Dec 30, 2025

Not Feeling it

Dear UncleGary, My best friend just confessed they’re in love with me. I love them too, but not like that. Do I tell the truth or let them believe there’s hope? Signed, Not Feeling it Dear Not Feeling It, First off, this is one of those moments that calls for courage. Not the loud kind, but the quiet kind, the kind that shows up when you look someone you care about in the eye and tell the truth, even when it’s uncomfortable. Because love, in any form, deserves honesty. It des

How do I say no to friends trying to sell me things?

Dear Uncle Gary, How do I say no to friends trying to sell me things? Signed, Pitched in Portland Dear Pitched in Portland, Say no once, clearly. “I value our friendship, but I’m not interested.” If they keep pushing, they’re choosing the sale over the relationship. That’s not on you. That’s just good information. Signed, Uncle Gary