We've all heard dudes lament that flirting/hitting on girls/commenting on women's bodies is "only creepy when the guy is unattractive."
Some women boldly declare the same.
"If a sexy man compliments me, that's fine. If a ugly man looks at me too long, that's harassment." (See also: Here's How One Pretty Woman Deals With The "Constant Stares and Compliments" From Men.)
"It's only sexual harassment if he's ugly and poor." (See also: Yes, Money DOES Make You Happier - If You Use a Log Scale.)
"If he's cute, it's called flirting, but if he's ugly that's sexual harassment and you'd better go to HR." (See also: Why You Should Flirt With Basically Everyone.)
Sure, reality is harsh... but so is self-reflection. So let's "unpack" this a little to figure out what's really going on, and how you can do better in your romantic pursuits.
1. In order to be fun and not creepy, FLIRTING HAS TO BE MUTUAL.
Flirting is fun. But only when advances are thrilling, meaningful, or desired. Flirting, like kissing, sex, and... I dunno, tandem skydiving?... is only fun when both people are into it. (See also: Dear Confused Dudes: If You Had To Grab Her By The Head and Restrain Her, It Wasn't a "Kiss.")
Unwanted sexual advances are gross.
I'm not going to sugarcoat things, because that's a waste of everyone's time: if you're attractive, your advances are more likely to be mutual. If you're unattractive, your advances are less likely to be mutual.
Especially in a situation where you're chatting up someone new, who knows little about you other than what you look like.
Facts are facts. The only way around this is to pretend evolution and biology and psychology don't exist.
Yes, all else equal, women like men who are tall and handsome. BUT. What's going to be a lot more important than that in the long-run is his ability to provide. That he has mature and masculine qualities. That he is a loving, considerate, compassionate individual.
And that he's smart. According to Plomin and Deary's expert review, Genetics and intelligence differences: five special findings (2014), "Assortative mating is greater for intelligence (spouse correlations ~0.40) than for other behavioural traits such as personality and psychopathology (~0.10) or physical traits such as height and weight (~0.20)."
In other words, Hollywood is wrong. Opposites do not attract. We like people who are like us -- with respect to anything from political opinions to religious background to physical attractiveness to intelligence. But we especially like people who are like us with respect to intelligence.
But I don't know how intellectually sexy you are if we've only just met! And I'm going to assume you're intellectually repulsive if you think the way to win my heart is to give some cheap compliment about my body or appearance.
So if you're someone of below-average attractiveness, maybe instead of hitting on women you barely know... get to know them first. Learn charisma and be respectful. Remember: it's not that girls don't like guys who are "desperate" or "too available." It's that you ignored her clearly-stated preferences and boundaries.
Once they feel comfortable around you, once they start to appreciate your intelligence, sense of humor, and other positive qualities, THEN it may be time to start flirting.
2. I really shouldn't have to say this, but you're not entitled to a woman's attention.
Guess what? It's okay for women to be attracted to other women. It's okay for men to be attracted to skinny women. It's okay for men to only want to date women with vaginas, and it's okay for women to be attracted to nerds or jocks, or anyone else they want.
We are all allowed to be attracted to whomever we're attracted to, and you are not entitled to a woman's time, affection, or attraction.
That's why so many women cringe when they hear phrases like "friend zoned" and "nice guy."
Remember: no woman ever dates a man because he's "nice." Nice is the most basic criterion. If you're not nice and other things... then you're just nice. And that's, like, super boring.
If you feel like you don't have much to offer, other than being nice, check out some of the advice I shared in You'd Get Invited to More Parties if You'd Mingle, Instead of Cling.
And, again, remember: you are not entitled to a woman's time, affection, or attraction.
3. A decent rule of thumb is, "If you're not SURE the answer is yes, don't ask her out."
In July 2017, Ashton Kutcher, an American actor and investor, was berated on Twitter for trying to start a conversation about rules for dating in the workplace.
Which is absolutely ridiculous. It's a perfectly valid question. If we don't discuss "clear red lines" and rules for dating at work, we spread ignorance and fear. Male and female employees may become afraid to interact with one another. Women may miss out on opportunities to discuss promotions and raises, because their bosses are afraid to have a closed-door meeting with them. Bosses may fear asking employees out for a drink to discuss a project, for fear this could be interpreted wrong.
And, of course, women (and men) could get hurt, by both malicious and well-meaning colleagues.
We should absolutely be discussing the rules for dating (and even friendships) at work.
I don't have a great, all-encompassing answer. But the advice I gave one friend recently when he wondered whether or not he should ask out a woman he works with was, "You should only ask if you know the answer is going to be yes."
How do you know the answer is going to be yes?
You spend time talking to each other at work. You feel a certain mutual energy -- not a one-way physical attraction. It's obvious to you that she likes you and would want to go on a date with you.
If you don't know she would say yes, you either need to practice developing your social skills or get over this girl. Because either you don't have the social savvy to stay out of trouble, or you're asking because of wishful thinking.
And she shouldn't have to feel uncomfortable and objectified by some creepy dude she doesn't even like just because you were too lazy or emotional to examine and correctly interpret the interactions.
4. Hot guys can be creepy, too.
It's not like being attractive gives you a free pass. Look what happened to Ashton Kutcher when he asked a sincere and important question about dating at work.
Undoubtedly, part of the reason women seem not to find hot guys as creepy is your own motivated reasoning. Your mind clings to examples that confirm your existing views. It selectively forgets or overjustifies examples that don't. Even the world's best thinkers are prone to cognitive biases.
And, yes, part of the reason women don't seem to find hot guys creepy is the whole, "If there's a mutual attraction, it's not creepy," thing.
But another part of the reason may be that attractive men simply have more experience talking to and flirting with women. Communication is hard and messy, and the only way to get good at it is through practice.
If you spend a lot of time watching porn and playing video games, you're not going to be as good at flirting or communicating as someone who goes out to bars, joins co-ed sports leagues, spends time pursuing hobbies, and makes plans to meet up with friends.
THAT SAID. Hot guys can be creepy, too. I've met my share, and no amount of physical attractiveness makes it acceptable to harass women.
So, long story short, yes. If you're physically unattractive, you may have to approach flirting a little differently from those despised "hot guys."
But one thing you can do right now, that will instantly make you more manly and attractive, is think about what behaviors of yours might be problematic... and how you cn correct them.
Because, to me, one of the major differences between a man and a boy (and, for that matter, a woman and a little girl), is that a man takes accountability and doesn't blame his faults on other people.