You got it, John! I think that's the best way to not seem like a creep. Stay away from the body parts and stick to the jewelry or shoes. Or, just smile and be friendly. That always feels good!

It depends on the woman, and the timing.

A co-worker of mine thinks every man who pays her a compliment "wants" her, gets all offended and trashes him every time she sees him from then on.

On the other hand, a stray compliment or two would thrill me, as long as it wasn't inappropriate or at an awkward time.

I remember a girl in high school the told me she liked my shirt. That was about 55 years ago and I have never forgot that or her name even though she moved away and never saw her after she moved.
I think if you have a problem with a compliment that you have other problems too.

"Random" interactions are well, random. Unless you know a person and the situation (and sometimes even if you do), it can be difficult ot predict reactions.

I think it always "depends." Depends on the compliment. Depends on the woman. Depends on the situation. Depends on how important it is to you to get a specific response.

In the workplace, I think it's better to err on the side of caution, but in "random" situations I'd say go with your instincts unless you have reason to distrust your instincts (for example, if you regularly get negative or confused reactions).

This thread is making me sad! I love compliments, and sadly, love them most from men!! Missing a few from my dad? Maybe, but I love sincere compliments from men. I hate that we're going so PC that men are terrified to give a woman a compliment! One man's compliment on a progress picture of mine, and only Matt H has ever been brave enough to do it, is worth as much as 10 from the women.

I think it's because I know men only give compliments when compliments are warranted. Women tend to give compliments much more freely and not necessarily with sincerity but more as a "feel-good" thing.

I say, give the compliments, as long as they're not creepy. Pick up lines are never good. But, "Wow, you have beautiful eyes." Yeah, that would make my day. That would make my week!

I agree with JohnP
Clothing, shoes, accessories are fine. Features can be misconstrued as "hit on lines"

Ha! I don't know that I'm terrified but I don't want to be a "creeper" so I just keep my mouth shut. The goofy part about you women is that two guys could say the exact same thing in the exact same way in the exact same circumstances but it will be taken differently based on
A) The mood of the female.
B) The time of the month
C) How attractive the woman percieves the male to be
D) ???????

I learned long ago us average looking guys can't get away with the stuff good looking guys can. I can't wait till I'm in my sixties and I can become a dirty old man lol. I'm going to be complimenting you ladies left and right without a care in the world.

Too funny!
I am ok with appropriate compliments from guys. If I feel it's verging on creepy, I find a way to mention my DH.
Ex:
You have amazing ears!
me: thanks! My husband likes them too (in a nice, not sarcastic voice).
Dorky, but effective, and I still get to acknowledge the compliment.

I love to get and give compliments. I know how much they mean to me and can serve to turn my day around. I can see the reaction from both men and women that they too feel the pick-me-up!

I am cautious about what I refer to when giving the compliment and stay away from body parts except for maybe eyes. I will comment about striking eyes but not to a stranger. Ears - creepy (shudder) too intimate.

Maybe a compliment on a person's demeanor as a place to start - "You're looking happy/energized/confident/calm, etc today" whatever the situation may call for. Even if they didn't feel happy, etc I bet they do now or at least better.

Or you can start with an opening question - "Can I pay you a compliment? or can I just say..pause..You have great taste, that necklace/scarf-tie/hairstyle/dress makes the outfit/is a nice touch/is a good color for you."

I like when I'm complimented, if done tastefully of course. It's nice when others notice the good and even nicer to hear it. I think there should be more kind words exchanged from one person to another, there's too much hate and distance in this world- I'm a bit of a hippie at heart.

I'm not completely terrified, it's so hard to gauge beforehand.

I should probably clarify, my idea of random would be a stranger but some circumstance would bring about an exchange, not just walking up to a woman and making some comment, i would never ever do that. I just don't want to be misconstrued as a weirdo stalker or something.

I'd have to say go for it, as long as you're sincere.

Chances are, the woman will appreciate it, even if she seems a little taken aback at the moment, she's probably going to be thinking about it later and be really flattered.

I'm in the camp that thinks more kindness in day to day life can only be a positive thing. Yes, someone could be having a bad day and not have a great reaction, but like I said you probably just made it better for them! Good luck!

Life is too short to withhold a compliment. As long as it isn't a compliment about any part of her that's normally covered by a bathing suit or doesn't scream "Creeper!" I say go for it.

"That color/necklace/pair of boots/jacket/whatever really suits you" is almost always nice. So is a compliment about something slightly more personal like eyes or such if it's prefaced with an "I hope you don't mind my noticing, but you have a lovely smile/beautiful eyes/such nice hair."

The world could use more kindness. I think it's lovely that you want to pass along the glow of pleasure you felt at the compliment you received. And I don't think gender enters into it at all; I love to compliment men as freely as I do women and I appreciate a compliment from either equally.

If I would appreciate a woman telling me I look great in purple, why would I assume that a man who said it was judging my attractiveness or hitting on me?

Because a hetero man wouldn't tell another hetero man, Nola. And because you wouldn't assume that your opinions were relevant if you were interacting with your boss's boss, or the president or owner of the big company you work for. The structure of the interaction-- person receiving either smiles gratefully or looks like an arse, maybe because she's "having a bad day" or "it's that time of the month" (which was suggested upthread)--boils down to the giver is exercising his or her power over the receiver; the receiver has no choice but to be nice about some totally unrequested input from a total stranger.

Women, particularly young women who appear to be of near-normal weight, hear a LOT of unasked for input about what they look like. Part of how our society works is that this is somehow supposed to be okay, that any random person somehow has the right to tell me or you or her over there about what s/he thinks about my or your or her eyes or hair or face or clothes-- that any random person's opinion is supposed to be relevant.

But a hetero male would tell another male 'nice ride' complimenting him on his choice of vehicle or motorcycle, etc. The compliment is given in an area one man would assume would be received as a compliment by the other man.

We are not discussing a work place environment - just a casual stranger encounter. I often think of these situations occurring in line at the grocer's or a coffe shop, etc.

Relevance is what the receiver gives it if she gives it any relevance at all. The receiver has the power to do with it what ever.