My buddy told me I treat hangouts like meetings, so I stopped booking 3 weeks out

Faith Mason · 2026-10-20T05:20:03.19829+00:00

I used to book everything 2 to 3 weeks ahead. Calendar invites and all. Then my friend Dana told me point blank, "Hanging out with you feels like a dentist appointment." Ouch. She was right. I was so scared of people flaking that I over-planned every single thing. Now I just text "free tonight?" and grab tacos at 6 if they say yes. Last Thursday three of us ended up at a diner until 11pm on a total whim. Kind of wild how much better it feels. How do you all balance wanting plans with not scaring people off?

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My buddy told me I treat hangouts like meetings, so I stopped booking 3 weeks out | Adult Friendship Rules - Rigidtalk