Guys, Watch Out: 4 Red Flags in Dating and Strategies to Handle Them

I’ve been pretty active and successful with relationships and dating and I can tell you one thing: plenty of women are not worth your time. Many are boring, others are entitled, and some have ‘double standards’ written all over them. Here is how to recognise them and what to do.

We’ve all seen videos where some young woman says she would only date a guy who makes six figures, spends a grand on a first date, buys her a 1M$ wedding ring, or some other such infuriating crap.

It’s not just about money, either. You’ll find videos with women who can barely string a few grammatically correct sentences yet feel entitled to dating the smartest, kindest, most interesting guys. And while these are obviously the most extreme outliers (that’s why they get popular!), it’s also true that many women out there can be pretty crap in a whole range of ways.

Infuriated men spend hours commenting and debating. I get it — particularly as we’re told it’s guys who are always the bad ones and women are pretty much born perfect. But is it really the best way for us to deal with this? Getting pulled into pointless discussions and letting our blood boil over what? What exactly are you getting out of it?

So yes, let’s recognise that women can absolutely be all sorts of crap in dating. Red flags all over. But what should we do about it? Here’s your field guide to dealing with four common problems. Read until the end to get a general model that will help you address similar cases.

Please don’t think this is some God-given wisdom that I have always perfectly applied in my life. No. These are some hard-earned lessons which I am very aware are much easier to present in theory than to enact in practice. If I list some things you should NOT do, it’s most likely because I’ve done them and they blew up in my face.

I’m not perfect. I just have a lot of experience.

Women who expect men to always lead in life, dating and bedroom

It’s the 21st century. At least in the Global North, women are perfectly capable of taking care of themselves and there is nothing stopping them from initiating romance.

Honestly, I’m tired of women who wait for me to be the driving force in dating. It’s exhausting to make all the effort and take all the risk of rejection. It’s frustrating to know that if anything goes wrong it will always be my fault — of course she’ll never do anything wrong if all she does is wait for me to do things!

How to spot this is about to happen? Here are some questions to help you decide if this is what’s happening:

Does she expect you to always come up with ideas for things to do, pay for every date, be taller, richer and more sporty?
Does it feel like she’s waiting for you to make every next move but won’t put the effort or take the risk of making a move herself?
If you matched on a dating app, did she wait for you to start and drive the conversation? Did she send only very basic messages?
Does she expect you to ask her questions but doesn’t ask much back? If you don’t say anything for a minute, does the conversation just die?
Does she make sex your sole responsibility, taking no initiative in the bedroom, expressing no own desires, yet making it all your fault when she’s not satisfied?

If so, there are two explanations. First, she’s just not that into you. Sorry. It’s best you realise that early on because you’re just grasping at straws. Stop wasting your time and move on. Plenty of fish.

Second, she is into you, that’s just how she behaves. If so, you’re in danger of pursuing someone who will likely make you feel unhappy and exploited. It might seem nice at the start — after all, you’re impressing this girl with your awesome active leadership. But it gets really old really quickly because you will always feel like you have a follower, not a partner. Even if all you’re after is sex, there’s only that much one can do with a starfish.

Unless you do something about it.

Whenever I start seeing a woman and any of those issues come up, here’s what I do and recommend:

Play the lead role for one or two dates. Maybe she’ll pick it up. If she does, awesome, no issue.
If she doesn’t, encourage her. Ask what she wants to do. Say you’re open to things developing and invite her to make a move when she’s ready. Ask about her fantasies and how she likes to be touched. If she picks it up, awesome — though keep monitoring it.
If she doesn’t, first assume that she wants to but something prevents her from doing so. Women are still socialised to be more passive and prioritise the needs of others. Some have bad experiences with ex-partners. Try to address this by showing her that she can feel safe with you and that you won’t judge her for taking the lead role. Have an open conversation about this and say how you feel. Say you would rather be dating a more active partner and if you can do anything to support her in being one. If you see that something is changing, that’s great, but be aware that this might take some time and effort. Judge for yourself if you are up for helping her with developing on this front. Talk to your friends and ask their opinions.
If you aren’t, make sure to end it in a kind and respectful way. Say that you really appreciate her trying but you just don’t have the capacity to help her now. Wish her all the best and warmly encourage her to keep working on this.
If you are, simply continue encouraging and rewarding her for taking initiative. Make sure to continuously check if there’s progress.
If there is no progress or she wasn’t open to it from the start, then end it in a kind and respectful way. Wish her all the best and go your own way.

Now, here are three things to NOT do when this happens, at any point in the above process:

Make her feel horrible for not being what you want her to be. That will only make the situation worse because she will be even less likely to take initiative, fearing whatever she does won’t be what you want.
Say nothing and keep dating while building up resentment and anger, only to blow up at some point when you can no longer hold it in. This way you’re not only not helping and likely making it worse — you’re also ensuring that once it all inevitably ends, everybody will think it was your fault. Even if your feelings were justified, nobody will stand on the side of the angry resentful man, especially if in your anger you harm her.
Make unjustified generalisations implying that all women are like this and spread them off- and online. Not all women are like this, you’ll look like a bitter jerk to everyone except other men who feel the same, and you’re getting yourself in a mindset which will jeopardise your confidence and future prospects with other women.

Before you call me a smartass, remember — I’ve made all of those mistakes in dating and I’m not judging you for making them. We’re human and we all sometimes do the wrong thing because it gives us bitter satisfaction or because we’re focusing on our present pain instead of the big picture. But trust me, you will be way better off once you stop.

Women who are very keen on equality when it benefits them, but not when it requires them to put in some effort

Humans are lazy creatures by nature. We all tend to follow the line of least resistance whenever we can. We all get quickly used to a good thing but can’t force ourselves to do that which takes effort.

One of the ways this exhibits itself is when some women want to have their cake and eat it — they want to overthrow the patriarchy, except for the parts which benefit them. Sometimes they rationalise this with appeals to historical justice — women have suffered oppression for centuries, so now I am entitled to take it all back.

This might work on some systemic levels where affirmative action to include more women in government or tech industry can serve to correct past inequalities and discrimination. But it rarely works on a personal or relationship level. The fact that her great-grandmother couldn’t have a bank account doesn’t mean she can exploit you now.

If you find that the woman you’re dating is very keen on equal distribution of house chores, power dynamics and sexual satisfaction, corrects you on anything even slightly insensitive and is quick to point out any microaggressions, well, mostly that’s great. But not if at the same time she:

Expects you to earn more than her and pay for her or give her expensive gifts she doesn’t feel obliged to reciprocate.
Expects you to take care of her and protect her from anything bad without offering the same in return.
Says men should be more emotionally intelligent and vulnerable, but makes you feel bad when you are feeling down or weak, or only lets you express negative feelings when they’re not about her.
Requires you to tend to all of her needs but doesn’t tend to yours in equal measure, including emotional and sexual needs.
Asks you to validate her appearance and make her feel beautiful but never does the same for you.

I’ve been in situations like this and I thought I had to agree to bad treatment in the name of my commitment to feminism. I don’t think that anymore. Humans are humans, if you give them an inch, they’ll take a mile. Unless you do something about this quickly, it will only get worse. In dating and everywhere.

Based on my experience, here’s what I recommend:

Openly talk to her about this, with the assumption that she has likely been socialised to act and think this way — it’s not out of ill will or wanting to exploit you, she is simply unreflectively playing from a cultural script. Say that you are very happy to revise the house chores, power and other scripts which discriminate against women, but you ask that she joins you in revising the earnings, emotionlessness, and other scripts which make life worse for men.
Have a good think about your own boundaries and discuss them with your friends. What are your hard limits? What are the points at which you say: I’m not OK with being treated like this? Communicate them clearly to her, making sure you stay kind and understanding.
If she is open to having these conversations and wants to change, remember that this will not happen overnight. It takes time to revise cultural scripts. Be ready to gently bring things up when they occur and have more compassionate conversations.
If she is not open to these conversations or she says she wants to change but despite multiple gentle reminders she never does, stop dating her. Have a calm and kind conversation where you say that you think that she needs to change her approach but you no longer have the patience to support her in that journey. Wish her all the best and move on.

And what NOT to do when you find yourself in this situation?

Retaliate by going back on your commitment to treating her equally concerning chores, power dynamics, etc. Two wrongs never make a right.
Say nothing. You might think you’ll be OK, but slowly and silently the balance of what is considered ‘equal’ or ‘normal’ in your relationship will shift. When you eventually start asserting your needs and trying to shift it back to the middle, it will seem like you’re making unreasonable demands. Old habits are hard to break, you need to address them before they form.
Be angry about it and make your conversations about blame and complaining. It will make her feel attacked, the whole thing will become a feminist issue of a poor oppressed woman against an angry man, nothing will ever change, and most people will side with her and think you’re a jerk.
Make unjustified generalisations implying that all women are like this and spread them off- and online. Not all women are like this, you’ll look like a bitter jerk to everyone except other men who feel the same, and you’re getting yourself in a mindset which will jeopardise your confidence and future prospects with other women.

Fortunately, I found that the great majority of women are perfectly happy to acknowledge that they might need to change to also respect your equality. It just takes a kind and calm conversation.

Women who think that men are the source of all evil

To be fair, this is a pretty rare species. You wouldn’t think so if you live online, because their voices get amplified to no end and spark the most heated click-bait discussions. But it’s like with shark attacks — everyone talks about them but in real life, they are very, very rare. It’s just the sort of thing that gets people’s blood pumping, so it gets blown out of proportion.

But many more women think that many men are the source of a fair amount of evil in the world. That might be factually correct but can be pretty tough to deal with when it centres on you. Either way, something is not right if a woman:

Makes you personally responsible for centuries of sexist oppression, war and violence.
Berates you for the same behaviours she would excuse in women (except in justified cases when power imbalances mean that the same behaviours do in fact have different imports).
Has an evil ex who is guilty of everything bad that happened to her and thinks men are to blame for all ills in dating.
Regularly engages in heated off- or online discussions where she insults and belittles men and doesn’t want to hear their point of view even when it is respectfully expressed.

You might simply not want to engage with women like this. That’s fair enough. If so, simply walk on and let them be.

But the thing is, more often than not these can be wonderful people who have simply learned to put up a strong façade as a coping mechanism or a way to deal with some past trauma. Often, they expect the worst of men because somewhere in their past there has been a man or men who have hurt them.

If you do want try dating such a woman, the best way to do so is to try and pierce this façade with kindness. Here is what to do:

Very obviously don’t be who she expects men to be. Don’t be violent, angry, sexist, entitled. Instead, be a living proof that #NotAllMen — be kind and generous, treat her with respect and understanding, and make her feel heard and seen as a person. Note that this does NOT mean you should be a simp or a doormat — you should still assert your boundaries and not allow her to ignore your needs, as stated in the previous section.
Talk to her about her worldview and challenge it, but do so coming from the point of kindness and understanding. Acknowledge that she has reasons to think what she thinks, but help her see that it’s not the whole picture.
Try to meet her halfway — even if she’s making everything seem worse than it is, there is still likely more than a grain of truth in her worries. Read some of the stuff she reads and have constructive discussions where you respectfully share your perspective.
Remember that she will not change her perspective overnight. It takes time to revise deeply held views, especially if they are rooted in trauma. Be ready to gently challenge her and have more compassionate conversations.
If she is not open to change, stop dating her. Just leave her be or, if you got invested, have a calm and kind conversation where you say that you think that she needs to change her approach but you are no longer able to support her in that journey. Wish her all the best and move on.

Just as before, there are some things you should definitely NOT do:

Say nothing, internalise her criticism and let her walk all over you. You will lose all self-respect and become her puppet.
Decide to stop dating her but instead of just moving on, turn it into a battle and feel you need to prove her wrong. She will only get defensive and take everything you say as evidence that men are horrible. All you will gain is stress and likely criticism from people watching. You might get validation from other guys but at the cost of making yourself look un-dateable to most women.
Make unjustified generalisations implying that all women are like this and spread them off- and online. Not all women are like this, you’ll look like a bitter jerk to everyone except other men who feel the same, and you’re getting yourself in a mindset which will jeopardise your confidence and future prospects with other women.

Are you noticing a pattern here with not making unjustified generalisations or spreading hate? Seriously, guys. There are seriously troubled and outright shit women out there. Whatever. Don’t make it look like they are the norm, don’t give them attention, just move on.

Women who don’t make you feel valued, wanted and desired

Honestly, this whole thing with men being the pursuers and women the pursued? All this responsibility to chase after her while she’s just sitting there waiting for suitors to show up? All the pics of hot women getting millions of likes while way better pictures of hot men are barely noticed?

I’m so tired of it. I’m so done with a culture in which physical admiration and sexual desire seem to mostly just go one way. I’ve had it with princesses who feel entitled to receive all the attention but aren’t interested in giving much back. I’m exhausted with women sending signals of interest so sparse and subtle you need a microscope to see them.

I have frankly no time for women who:

Don’t give you compliments
Don’t make you feel valued for all the things you have to offer
Are not particularly interested in admiring and cherishing your body, both during sex and in general
Have little or no sexual imagination or ideas for what they’d like to do with you in the bedroom
Don’t make you feel like they miss you when you’re apart
Rarely go out of their way to do something nice for you
Once you’re together, they no longer try to seduce you

If that’s the sort of woman you find yourself with, you might still do something.

Ask yourself: is she at all interested in dating you? Maybe the truth is, she’s just not. Maybe you wish she was but she isn’t. If so, stop beating a dead horse. This isn’t going anywhere. The longer you pursue it, the more disappointed you will be in the end.
Ask yourself: are you that desirable? Are you a good lover and partner whom she could genuinely want? Maybe it’s time to hit the gym a bit or pick up some hobby that will make you more interesting.
Ask yourself: are you offering all of those good things to her? Maybe she’s not giving it because she feels like she’s not getting it either. If so, perhaps it’s time to up your game.
But in my experience, women still often act like that even if you totally are a great catch, you are attentive, and she is in fact interested. If so, assume that this is the result of the way she was socialised and she just doesn’t know any better. Don’t blame her for it, don’t reproach her — invite her by saying what you like and be most gracious when she does it. Have an open conversation about it. If she opens up to it, awesome.
If she doesn’t, just leave. Honestly, no second chances on this one. Have some self-respect and don’t be with someone who doesn’t make you feel special.

Whatever you do, make sure you don’t:

Say nothing. You will forever feel bad, you might develop an unhealthy need to prove yourself to earn validation, you’ll lose your self-esteem and confidence, and if you break up you’ll find it hard to believe in yourself when you start dating again.
Resort to blame, reproach and arguments to get her attention. You can’t force anyone to want or desire you. It has the opposite effect — you just make yourself unattractive and give her reasons to not want you.
Resort to retaliating by withdrawing attention and all the good things yourself. It will only lead to more bitterness and resentment.
Make unjustified generalisations implying that all women are like this and spread them off- and online. Not all women are like this, you’ll look like a bitter jerk to everyone except other men who feel the same, and you’re getting yourself in a mindset which will jeopardise your confidence and future prospects with other women.

Women are not a scarce resource

Guys who either agree to dating such women or keep raging online about how horrible they are, typically have a scarcity mindset. They think that they desperately need a girlfriend and thus either agree to anything or get angry every time things don’t work out.

What most men need, is a big chill pill. You met a woman who seems pretty shit? Yeah, whatever. Humans can be pretty shit, big news.

You don’t need to make a huge deal out of it. You’re wasting your time and creating more division. Just move on.

All my above advice is just an elaboration on this simple model you can apply when you meet anyone who seems shit:

Ask yourself: is this person worth your time?
If yes, figure out why she’s like that and if it can be changed
If yes, assess whether you have the strength to help her change
If yes, continue monitoring if the change is in fact happening
If yes, awesome, enjoy having a great relationship
If any of those is a no, don’t engage, break up in a kind and respectful way, and move on.

Do not stay in a relationship that is bringing you down.

Do not go on a crusade to destroy her and everyone like her.

Neither is worth your time and both only make things worse.

Just.

Move.

On.

PS. Yes, I know there are plenty of women who should also just move on yet are bitching about men instead. That’s a topic for another text and it’s not an excuse to be equally bad. Two wrongs don’t make a right. Be the better man.