First and foremost.
Catcalls are not compliments.
Catcalls are the attempt by one person to draw the attention of the other person to them for their own benefit. Here's a Buzzfeed article that discusses it.
Catcalls are directives — Turn around! Come talk to me! Let me see that smile!— which assume at their most basic level an ownership of the woman being catcalled. These aren't innocuous or playful requests; they are symptoms of entitlement, and messages that women don't deserve control over their own bodies.
By catcalling, harassers insert themselves into the personal space of the harassed: during her commute, her daily jog, her walk to brunch. This puts unwilling women on the defensive on a daily basis, where ignoring the comments isn't seen as an absence of a reaction but instead a transgression, or justification for more verbal assaults.
If you want the attention of another person and you do not consider how they feel, don't do it, especially if you're male and they're female and you don't know them.
Yes, there is a (possibly sizable) group of women who like this - consider it an ego boost... but you are more likely to find that your catcall causes them to be uncomfortable - and why risk it?
And here's a Daily Beast article:
Activist group Stop Street Harassment commissioned a national US study of 2,000 participants. The study's findings were disturbing. "The survey found that 65 percent of all women had experienced street harassment. Among all women, 23 percent had been sexually touched, 20 percent had been followed, and 9 percent had been forced to do something sexual.” And we're not even talking about the horribly harassed public life forced on many in the LGBTQ community.
Men need to ask themselves some questions before speaking, like:
- Why am I telling a woman what I think about her appearance?
- Is it an appropriate place to do so?
- Is there some kind of rapport that makes it okay to convey this without seeming like a threat?
Women have made their voices heard and, if you care about other people, you’ll take steps to actually make spaces safer—not contribute to environments that make it worse.
You can have the best intentions but still contribute to an environment that makes women feel unsafe. I, and many fellow men, know this because women say so—they write it, they lecture on it, they write books about it. There’s no excuse for men to be ignorant about what women experience. To disregard that for the sake of instant gratification from women’s attention seems morally negligent. To dismiss it as just “boys being boys” only adds more fuel to the fires where animalistic natures are given fresh life, burning away any notions of being a person or an adult.
So, when is it OK to compliment someone?
As a woman, I find it much easier to accept (or at least entertain) compliments from other women (regardless of whether I know them or not) or from men who I know.
It's very rare that I personally feel comfortable getting complimented by a man but it has happened and usually it's because they've done something like what's in your example and the tone it's spoken in has to convey a level of open honesty that doesn't feel like the person is attempting to get something from me.
Additionally, once the compliment is shared, don't require anything further from them. Make it brief and quick and walk away. You complimenting them is not an opportunity to get their phone number. The problem with catcalls is that, positive or negative, they request/require a response from the target. A compliment doesn't require anything.
I wanted to let you know that you look amazing today. Have a great day! [exit stage right]
Alternately, it helps if it's more of a fact-finding compliment than a pure one:
- I really love that jacket, I think my girlfriend/mom/sister would like it, could you tell me where you got it?
These two points sound contradictory but they serve different purposes, so it's different.
If I were having a conversation that turned into a compliment. A ten-minute chat about the book I'm reading on the bus would make me more able to accept a "you have great taste in books" compliment or even a "You look so happy when talking about this book that you love so much"...
If you really feel like you need to compliment someone, think about it first. Consider the three points from the Daily Beast article I quoted. Be empathetic and consider things from the receiver's side. And, if you get a negative response, apologize, don't get defensive. You're the one who started the interaction. They don't have to accept your compliment.