That's a good one.
I've actually used something similar last week, "Hey, what would you think if I showed up on our first date wearing this shirt?"
It followed with:
"Are you asking me on a date?"
"Yes, but I'm more concerned about the shirt. Does the color match my eyes?"
"...yes, it does."
"Good, I hope you'll be impressed. Let's meet tomorrow at .... at 8."
"Wait, are you serious?"
"No, you got me. Let's meet at 9."
Automatically started reaching for the phone, she put the number in, exchanged the names, texted her, met up with her. Saw her again this weekend.

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A morning of awkwardness is far better than a night of loneliness.
18 Body Language Mistakes I Bet You're Making