The reality is this, some older guys can pull off compliments/mild flirting and it’s nice. Very easy to smile back and enjoy the brief interaction. Other guys make your skin crawl when they do the same thing.
It’s not money or looks that makes the difference. I can’t quite put my finger on it.
I’m a waitress so it happens enough that I’ve wondered about why some older guys come across as sweet and others as creepy.
In my opinion, it comes down to intent. The guys who mean to convince the woman to be a conquest come across as creepy. Those who are just being nice because it makes you and them feel better do not give off that creepy vibe.
As a middle aged man, it helps me to stay on the nice side when I keep my 30+ year marriage in mind! LOL
Have a great day, FRiend.
I figured it was largely whether they were just paying a complement, or paying a compliment in pursuit.