Woman pulls up to a gas station, where other people put gas in your car, for you. After saying hi, and how much she wanted, the Man tells her she looks pretty (she is wearing a dress) and asks what she did today/what was the occasion. She doesn't direct make eye contact, but gives him a lengthy answer that she went out to dinner, with her family, and did something else. Would you think she was trying to give him a hint, by specifically mentioning, that she went out to dinner, with family?
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I wouldn't have picked up on any kind of hint in a situation like that at all. I would have assumed that she was uncomfortable because of how she was avoiding eye contact.
Do you think the guy, or any guy in general, shouldn't tell someone they look pretty? Is that automatically creepy to you?
No, that's not automatically creepy. I give lots of women compliments. You have to remember that communication is a two-way street. Just be sensitive to the fact that even if something you're doing is normal to you, the fact you know what your intention is doesn't mean that other people do, and you never know what kind of weirdness might be floating around in someone's head.
You think you're saying "hello, I like your dress" but she hears that and has a PTSD flashback to the times her dad's friends got too friendly with her at neighborhood cookouts.
No, not even close.
Do you think the guy was outta line for saying that in the person, I'm sure he was just complimenting?