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As a general rule, it’s best to avoid all emoticons when you’re still in the early stages of wooing a girl, but the winking smiley can sound the death knell of your courtship faster than you can say “how do you feel about threesomes?”.
You think: this comes across as fun and cheeky
She thinks: I’m not having sex with you
Hard to imagine that just one little character turns a nice, innocuous “Wanna do something tonight?” into a sleazy “Wanna do me tonight?”. Save your fun and cheeky side for when you’re talking in person.
See also: poking someone you’re into on Facebook
Oct 19, 2012