LET IT OUT LISTS

LET IT OUT LISTS

kill 'em with kindness or?

mean is cool now? am I 'good with people still?' 🥴 what happens when I confront my fear of confrontation...

Katie Dalebout's avatar
Katie Dalebout
Jul 29, 2025
∙ Paid

Early on, I figured I wouldn’t be the smartest or the prettiest in the room—but I could be the nicest. That felt like it was within my control. So I kept in touch with everyone I ever met. I made a point to show up to anything I was invited to, check in often, and remember the names of people’s bosses, aunts, and hookups—even if it wasn’t reciprocated.

Social currency was the currency I had, so I used it. Like Dorian Gray used his beauty to distract from the rot underneath, I used likability to distract from my ineptitude and insecurity.

My ability to connect with people got me jobs, roommates, opportunities—when I least expected it or deserved it. It wasn’t just who I knew, but who liked me. I know being perceived as approachable is a privilege—not everyone has the same ease because of identity, mental health, or simply personality wiring that falls outside the cultural mold of “pleasant.”

Still I prioritized my likability like a craft, which meant every single relationship felt like a high-pressure situation. I studied and practiced being effusive, encouraging, and above all, a good hang.

But the culture is telling me people want black cats, not golden retrievers. That nice is uncool, and brat is cool. Too eager to please comes off as insecure—or worse, manipulative. Edge and boundaries read as confidence. Aloofness signals mystery and power. Overt friendliness can feel try-hard, or even strategic.

In the ever-changing landscape of how we relate to each other, it seems that speaking up for your needs is cool—especially when you do it directly.

Was this always true and I just never realized it? Beyond what’s trendy, directness is efficient. I’m all for it, but becoming more direct has been real rocky. Maybe because I spent so much time trying to be liked, I never learned what I like—or what to directly ask for?

Or maybe I’m dragging my feet on changing because there’s a grief to realizing the social skills I honed don’t buy me what they once did. I’d trained to be a supportive welcome mat but is everyone looking for a velvet rope?

The most compelling qualities now aren’t overt care or agreeableness—they’re self-possession. It’s the ability to claim your desires unapologetically. Self-possession is the opposite of nervousness, and it is hot.

I’m always nervous, so I end up talking to remove every awkward silence. I recently found myself explaining an inside joke to a group—only to realize silence would've been less awkward than my attempt to prevent it.

I saw how my talkative tactic to be liked by all had become my default mode when I visited my mom…

Keep reading with a 7-day free trial

Subscribe to LET IT OUT LISTS to keep reading this post and get 7 days of free access to the full post archives.

Already a paid subscriber? Sign in
© 2025 Katie Dalebout · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture