I’ll go ahead and assume you’re not hanging out of cars shouting at strangers because you know better.
With that in mind, there are things well-meaning people say, to women in particular, that aren’t compliments. Now, it turns out that there are billions of women in the world, and I don’t know all of them. Some women welcome various forms of attention, including a bunch of dudebros shouting nonsense from a moving vehicle.
However, I challenge you to consider whether or not you are really complimenting someone when you say or do the following.
“You lost so much weight! OMG are you anorexic? LOL.”
You want to congratulate someone and tell her she looks good. But what you’re actually saying is that a deadly condition is a punch line and that you monitor other people’s weight. I’ve been on the receiving end of this, and it’s awkward. What the hell am I supposed to say to that? “I don’t actually hate myself. Thanks for keeping tabs on my fat, though!”
If you know someone is trying to lose weight and you want to be supportive, there are lots of other things you can say without invoking serious illness or judging how they looked prior to their weight loss.
Hitting On Her While She’s Working
Service industry workers are expected to be friendly, pleasant, and accommodating; it’s their job to make customers like them. Even assuming that you haven’t mistaken this professional demeanor for a real connection, you’re putting a woman in an uncomfortable position when you ask her out while she’s working.
She could face any number of negative repercussions that affect her livelihood no matter how she responds. Instead of simply saying whether or not she’s interested, she has to manage your expectations as a customer/stranger who knows where to find her everyday and her boss’s expectations of her professionalism.
If you want to ask someone out, asking when she feels comfortable giving an honest answer that only affects her romantic life is the right thing to do.
“You’re not like other women. They’re all so dramatic/emotional/crazy, but you’re so chill/rational/calm.”
You’re trying to say a woman has qualities you value, but you’re really telling her that you think women suck and the more you associate her with womanhood, the less you’ll like her. It’s a messed up dynamic that can make people guarded around you.
Imagine if you framed other compliments this way. “You’re not like those other cops. You really care about people.” “You’re not like those other psychologists. You do real science.” “You’re not like those other freelance writers. Your writing isn’t a hobo’s garbage fire.”
If you want to compliment someone, you can do it without saying negative stuff about a group they identify with.
Romance is often framed as a man wooing and pursuing a woman until she says yes, which isn’t romantic at all. That sh*t is exhausting.
I know a man’s persistence is supposed to mean that a woman is desirable, but it also means that her words are worthless. It’s not a compliment to have someone ignore what you say or what you want. It’s actually huge red flag for a potentially abusive situation.
If you keep pursuing a woman after she’s made it clear that she’s not into you, you are definitely more concerned about your ego and what you want than her wants and needs.
“You’re way out of my league.”
People don’t say, “You’re way out of my league,” expecting the response to be, “Yup! That’s right.” This is not a compliment; it’s fishing for one.
Saying stuff like this means you’re romantically interested in someone, but you’re afraid it’s not mutual. It puts other the person in the position of saying you’re totally dateable in order to prove she’s not a jerk. It also means that when/if she says she isn’t interested you can throw her words back at her to make her feel awful and try to logic your way into getting a date.
If you actually like and admire someone, there’s no need to be passive aggressive. And if you want to date someone, being upfront and confident will get you a lot further than whining.