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Why would my date cringe at me telling him an old lady called me pretty on my way to meet him?
Anonymous
(25-29) 
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Did this older man just invite me to a date?
Anonymous
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How did he cringe if he wasn't there?
He asked if I found the place okay and I said yeah and decided to throw in her compliment because it happened like a few mine before he cringed and then raised his eyebrows
Maybe he is tired of hearing you brag.
Maybe tired of girls bragging in general that was about 10 mins into our date
For me, bragging is a big red 🚩 flag. It would only take a couple times for me to move on from that.
You should NEVER have to point out to anyone how wonderful/hot/smart you are. It reeks of insecurity and is big turn off. There is a quote I saw years ago that stuck with me.
"A 🦁 lion never has to tell anyone he's a lion".
Maybe he thought you were bragging