Do you find dating men confusing and exhausting? Before I changed my dating approach and met my husband, I definitely did, and my dating life was hell.

The dating pool is full of people who are lonely and unavailable. People who don’t know themselves, don’t know what they want, or don’t have the skills to build a healthy relationship. Some know perfectly well that they can’t give you what you want, but they waste your time anyway.

And if you’re like the younger me, moving from one country to another and using dating apps, you often have very little context of who these men are because you’re far from your communities and you don’t know theirs. You only know what they choose to disclose to you. You might find yourself wondering whether their behaviour is a cultural difference, or something you shouldn’t accept. There’s no social reference or accountability for it.

From your end, what you’ve learned about men, relationships, and your own needs can make it harder to process what’s happening and take action, even when you already feel in your gut that something isn’t working for you.

Here are 7 things that can keep you stuck, including conditioning you might not realise is shaping your decisions. Then I’ll explain at the end what you can do, so you can assess men clearly and act decisively in your own interest, even when you have feelings for them.

Feel free to watch the YouTube version!

When a man’s behaviour hurts you, your first thought is about what you did wrong and what it says about your worth.

Were you too direct? Did you bring it up too soon? Were you too emotional? Would he have responded differently if you’d been more chilled?

You can spend hours thinking about how you could have phrased a perfectly reasonable question differently instead of looking at why he refused to answer it.

This can come from what you learned early in life.

If you grew up in a family where your father’s work, time, and needs came first, you might have learned to adjust yourself around him without expecting him to do the same for you. When his absence hurt, you weren’t encouraged to question whether he was giving you enough care. You learned that he had important things to do and you shouldn’t ask for too much.

You learned that men’s needs and perspectives carry authority you shouldn’t question while your needs can be minimised. It might not even occur to you that your needs matter as they are, and whether a man’s behaviour works for you is something you get to decide.

On top of that, many of us grew up with magazines, films, and relationship advice that focused on how to get and keep a man interested. Be more chilled, don’t ask for commitment too soon, don’t scare him away with your feelings.

There are labels ready for you: “daddy issues”, “needy”, “stage-five clinger”. Your needs and reactions are always the problem, while the often emotionally stunted man who can’t meet your needs and causes you to have these reactions is considered ‘it’s just the way men are.’

You might have preferences for a man’s income, height, or appearance. You might want someone emotionally available who enjoys closeness and communicates consistently. But you feel ashamed admitting what you want because you’ve learned that they say something negative about you.

Wanting a man who earns well makes you a gold-digger. Wanting someone taller makes you shallow. Wanting reassurance and emotional availability makes you needy. You’ve heard that you’re too picky, nobody’s perfect, and who even are you to ask for so much.

Those messages echo in the background when you meet someone. You’re not attracted to him, but you wonder whether attraction should matter so much. You’re concerned about his financial situation, but you worry that caring about it makes you materialistic. You want more closeness, but you worry that your emotional needs are unreasonable.

It becomes almost impossible to decide whether someone is right for you or not when you’re judging yourself for the criteria you would use to make that decision.

After one disappointing dating experience, you might tell yourself you’re terrible at choosing men.

But when you look back, you may find that you noticed quite a lot.

You noticed that he avoided certain questions. You felt uncomfortable with how he spoke about his ex. You recognised that you were doing most of the work to keep the connection going.

Then you gave him the benefit of the doubt and continued.

When things eventually ended, you remembered that you stayed. You didn’t give the same attention to the observations you had made before you talked yourself out of them.

You might also dismiss the times you chose well. You stopped seeing someone early, so there was no dramatic ending. You said no to something that didn’t suit you, and your life continued peacefully. There wasn’t much to analyse afterwards.

That can leave you with a distorted view of your own judgement. Every painful outcome becomes evidence that you can’t trust yourself, and the painful experiences take up all the focus while the sound decisions barely get recorded.

Shrinking yourself in dating as a woman doesn’t always reveal itself as a problem at first because it’s rewarded as being pleasant, understanding, or easy to get along with.

You agree to a date that doesn’t suit you. You don’t mention that something upset you. You pretend you’re comfortable with the uncertainty because you don’t want to put pressure on him. You might even feel proud of how little you ask for because you don’t want to be seen as difficult.

Over time, you can become unhappy and resentful in an arrangement you appear to want. And you’re stuck. You realise you still have needs that are not met. You still want consideration, closeness, and a relationship that has room for you. It’s completely normal and valid. Hiding those things doesn’t remove them.

Continuing as it is makes you miserable, which you might not even want to admit to yourself because you’re already attached. And leaving is not easy either. The thought of starting over again is daunting, and you feel the pressure to make this relationship work to avoid your single life.

Dating has no entry barrier, no warning, no manuals. So you go on a date without having decided what you’re looking for. You meet someone you like, the chemistry is strong, and you think you’ll just go with the flow and see what happens.

So you text every day. You sleep together, spend weekends together, share personal things, and become part of each other’s routines. You’re doing things that build intimacy and attachment, but there’s no agreement about what this is, what you can expect from each other, or where it’s going.

By the time you realise you want a committed relationship, you’re already attached to someone who might never have wanted one. Now, finding out whether you want the same thing risks losing a connection that's become significant to you, so you keep it to yourself and spend your time suppressing your needs, trying not to be too much and decoding his behaviours instead.

Or you do know what you want. You’ve said it clearly to yourself and your friends. But once you become interested in a particular man, you start making exceptions while hoping that, as his feelings grow, a relationship will naturally follow.

You say you want to get to know someone properly while accepting dates after 10 pm when all you do is drink and have sex. You say you want commitment while continuing to invest in someone who has told you he isn’t ready. You want consistency, but you keep accepting a pattern that leaves you waiting.

Without knowing yourself and aligning your true desires with your actions, what you’ll get is dating on someone else’s terms and staying confused.

Sometimes dating feels confusing because you don’t have enough information. Sometimes you have information you’re struggling to accept.

He has said he doesn’t want a relationship. The same problem has continued after several conversations. You want different futures.

But you’re attached now. You look forward to seeing him. You’ve imagined what your life together could look like. There are things about him you genuinely love.

Accepting the situation would mean losing all of that, including the future you thought was becoming possible.

So you keep looking for another interpretation.

Maybe he needs more time. Maybe he’s scared because the connection is so strong. Maybe the lovely weekend means things are changing. A small sign of hope can carry enormous weight when you don’t want to face the alternative.

When you’re afraid you might never meet someone else, leaving a relationship can feel like giving up your chance at love. You’re deciding about this particular man, but in your mind, you’re also deciding whether you’ll ever get married, have a family, or have someone to share your life with.

That makes it difficult to assess the relationship for what it is. You might recognise that your needs aren’t being met, but then you think about your age, how exhausting dating has been, or how long it took to meet someone you liked. You feel you can’t afford to let this one go.

It’s harder still if you haven’t built a life you enjoy outside the relationship. If most of your companionship, plans, and sense of a future depend on him, leaving means facing a daily life you don’t want to return to.

Your standards and boundaries become difficult to hold because you can’t effectively enforce the ultimate consequence: walking away. You end up stuck between being unhappy with him and being afraid of life without him.

Make your relationship goal specific to guide your choices and filter out the wrong people quickly.
It helps to know more than “I want a relationship.” You need to understand what you want that relationship to bring into your daily life and what future you want to build. If closeness, regular communication, marriage, or children matter to you, those things need to be included in how you choose someone. Have the conversations that establish whether you want compatible futures early, before you become attached and start making exceptions.

Get more precise about what you know about a man.
There’s a difference between knowing he sent you a thoughtful message and knowing he’s a thoughtful partner. One is an event; the other is a conclusion that needs more evidence. Compliments, impressive dates, and talk about the future can show interest, but you still need to see consistent investment of his time, attention, and effort as he gets to know you. Base your assessment on specific examples over time, leaving room for what you don’t know yet instead of filling it in with what you hope is true.

Decide for yourself what’s enough and what’s acceptable.
You get to decide what you want in a partner, how you want to be treated, and what would make a relationship worth choosing. Other people might have different financial expectations, want less communication, or find someone attractive who you don’t. You don’t need their agreement to take your preferences seriously. A man can be impressive to other people and still add very little to your life. Your standards guide who you choose; your boundaries determine what you will participate in. Both require you to be willing to decline or leave an arrangement that doesn’t work for you.

Let your needs become visible while you’re getting to know him.
You need to participate as yourself to find out whether a relationship can work for you. That includes expressing preferences, asking questions that matter to you, and saying clearly when something doesn’t work. You can also decline something or end contact when you already know you don’t want to continue. When you do communicate a need, observe whether he listens, takes it seriously, and follows through. His response gives you information about his emotional availability, maturity, and willingness to build a relationship that works for both of you.

Give your own experience a fair place in the assessment.
You can consider his circumstances without making them the only thing that matters. He may be busy, stressed, or struggling, and you may still be receiving too little care or consistency. Understanding why he behaves a certain way doesn’t establish whether the relationship works for you. Include how you’re being treated, how you feel in the relationship, and what continuing as it is would mean for your life. Assess what he can offer now, rather than what you imagine he could offer once his circumstances change.

Separate your decisions from how you feel on a given day.
Once you’ve decided a relationship isn’t right for you, make the practical changes that support ending it: cut contact, block him if needed, and stop checking for updates. Set those rules in advance so a lonely evening doesn’t become another decision about whether to return. You can still miss him, feel attached, and grieve while keeping the relationship over. Give yourself some room to fall apart, then a date to start returning to your routines, without expecting the grief to be finished by then. Being firm about your actions doesn’t require you to suppress your feelings or recover on a deadline.

Pay attention to what happens after you act in your own interest.
When you express a need, end an unsuitable connection, or stop making an exception that hurts you, notice the result. You might still feel disappointed, but you may also have more peace, more time, and more attention for your own life. Look back at what you noticed about the situation and whether those observations proved accurate. Registering this gives you evidence that your judgement can be sound, even when acting on it feels difficult.

Accept that you might not find a partner, and build a life you want to live anyway.
Nobody can guarantee that you’ll meet the right person. That uncertainty can be painful, especially if marriage or having a family matters deeply to you. Accepting it means allowing for that possibility in how you build your life, while still making room for the relationship you want.

You need things outside dating that give you companionship, enjoyment, purpose, and a future to look forward to. These matter in their own right, and they also make it more possible to leave when a relationship isn’t right for you. If leaving means returning to a life you dread, it becomes much harder to uphold your standards or enforce a boundary.

Being in a relationship isn’t enough on its own to make your life better. The alternative to being single could be a relationship where you feel lonely, unsupported, or unable to be yourself. When you account for that possibility too, you can assess a man by the relationship you can actually build together, rather than treating having a partner as the prize.

​Why “ruthless”?

​When you’re used to being overly accommodating, giving endless chances or putting someone else’s feelings ahead of your own needs, choosing yourself can feel ruthless.

​This masterclass is for women who recognise patterns of people-pleasing, anxious attachment or overgiving. Ruthless means being firm in your structural decisions: your standards, your boundaries, who gets access to you, and when you walk away. You can feel deeply and still make decisions that protect your time, wellbeing, and future.

Get 20% off with code 20OFF until Sunday. If you’re my coaching client, I’ll reach out to you separately.

​In this live masterclass, we’ll cover how to:

​You’ll leave with a practical framework for knowing what to look for, what to accept, and when to move on, so dating becomes a series of informed choices rather than a running assessment of your worth - no more self-doubt and confusion.