Scenario A: You’re getting ready to go out and meet up with someone. You check yourself in the mirror and are pah-ritty happy with how you look. When you get there, they smile and tell you how good you look.
Feel good? Cool.
Scenario B: You’re getting ready to go out and meet up with someone. You check yourself in the mirror and are pah-ritty happy with how you look. On your way, you walk past a park where a bunch of guys are standing around. One guy whistles at you, another laughs and, when you don’t respond, the third guy starts walking towards you and says, “Oh hey, c’mon, we’re just having a laugh - lighten up, give us a smile…”
How you feeling now?
What’s the difference? You don’t know these guys, right? It’s a potentially threatening situation. Maybe they’re just having a laugh, maybe they don’t mean to be threatening, but you don’t know either way.
So, now…Scenario C: Now you’re one of the guys. And, just like the above scenarios, that hottie you spot walking along doesn’t know you either. You might think you’re giving a compliment when you say something. You might think they like it – a lot of people will smile in this scenario to avoid 'escalating conflict' – but the fact is, no matter what your intention, they don’t know who you are or what you want, and they probably don’t want to hear your opinion on anything, especially the way they look.
The short story is…
If you know someone well enough to know, without any doubt, that they would appreciate a compliment about their appearance, go for it (if that’s the most interesting thing you’ve got to say).
If you happen to see someone you don’t know and think they look good ...stay classy and just don’t.