Duckbill Diaries: The Hopeless Romantic Who Wants To Plan A Stand Out Date

Duckbill Diaries: The Hopeless Romantic Who Wants To Plan A Stand Out Date

Duckbill Diaries: The Hopeless Romantic Who Wants To Plan A Stand Out Date

38, Hopeless & Impatient Romantic, Houston

Oct 7, 2025

Oct 7, 2025

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DAY ONE
1:00pm: I’ve been seeing someone new and I really like them. It’s early, but I want to plan a standout date that says “I’m all in,” without being clingy. Low-key grand gesture energy.


2:15pm: Message Duckbill: "Help me plan a creative surprise date: something cool, not cliché. I’m thinking: romance via logistics."


DAY TWO
9:00am: Duckbill hits me back with options: 1) picnic setup in a hidden city park, 2) private tasting tour, 3) a pop-up dinner through a cool new organization I never would’ve found. I go with the pop-up one. It’s intimate and mysterious. Perfect.


5:00pm: They handle the res, Uber setup, and even include a note suggestion for the invite. I feel like the smoothest man alive. This is stealth mode romance at its finest.

DAY THREE
9:30pm: The date is a hit. We linger way past closing time. They say, “How did you find this place?” I just smile. Thanks, Duckbill.


Now to top this next time without overthinking it. Or... with a little help.


Want to submit a Duckbill Diary? Email deardiary@getduckbill.com and tell us a little about yourself.

38, Hopeless & Impatient Romantic, Houston

38, Hopeless & Impatient Romantic, Houston

Oct 7, 2025

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