How I Beat Texting Awkwardness
Okay, so last Tuesday I totally froze while texting my new hiking buddy. Sent a lousy “how’s your day?”… heard crickets for three hours. Felt like such a clown ๐คฆโโ๏ธ. Realized I needed texting training wheels.

Started by downloading every popular chat app – WhatsApp, Telegram, Instagram DMs. Couldn’t even message myself properly at first. Typed “Hey” to my own number like a total beginner. But hey, gotta start somewhere.
Testing Real Convo Starters
Grabbed my cousin Ricky first, since he texts like an emoji tornado. Tried random openings:
- Epic fail: Asked “How’s the weather?” Got back “Bro it’s JULY โ๏ธ” with an eye-roll GIF.
- Almost decent: Sent “Found this insane pizza place – ever tried squid ink pizza?” He actually replied! Said “Disgusting… but I’d try it.” Progress!
Then messaged my mom’s friend Ethel who uses 8 exclamation points per sentence. Learned seniors dig nostalgia questions:
- “What was #1 song when you were 20?” = Instant 4-paragraph reply with Beatles memories
- “Best life advice from your 30s?” = She sent voice messages for 15 minutes
Pattern Hunting
After two days of experimental texts, noticed something:
- Food & pet pics = universal cheat code
- Current obsessions > past experiences (“binge-watching anything good?” crushes “seen any movies?”)
- Impossible to fail with “If you had superpower for one day…”
Created a “5-min rescue list” on my notes app:

- Ask about their last great meal ๐
- Share dumb meme + “This made me think of…”
- “What’s currently living rent-free in your head?”
Real-World Results
Used my rescue list on coworker Dave yesterday:
- Me: “Saw Jurassic Park on cable – still terrifying t-rex or nah?”
- Dave: “DUDE the raptors!!! Kitchen scene ruined my childhood”
- Me: “What animal would you train to protect your house?”
- Dave: “Honey badger army. Send video proof of burglars crying”
Didn’t even need my other topics! Text chain lasted 32 messages about animal battles. Victory dance ensued ๐.
My Cheat Sheet Rules
After all this:
- Always start visual: Photos/screenshots = conversation fuel
- Weird > generic: “Weirdest thing in your fridge?” beats “how are you”
- Swap stories: Share dumb thing first (“spilled coffee everywhere today!”)
Now my phone keeps buzzing. Still mess up sometimes? Totally. But now I’ve got emergency topics in my back pocket ๐