Why is dating so frustrating and difficult for a guy?
12.06.2025 10:49
You were willing to go up against that final boss in that video game 50 times until you finally learned to beat it. Are you really going to tell me that’s more important to you than getting laid?
Learn to flirt. Flirting is a game, it is a technique. You give subtle indications of the woman’s desirability to you, but always subtle enough that you have plausible deniability. You learn to read her reactions. If she seems pleased, or flirts back, you can subtly escalate. If she responds the least bit negatively, you back off, and let it go, at least for now.
OK, first, most important piece of dating culture. Men are supposed to be the ones that initiate relationships. What’s this mean? It means the man must be assertive, the man must be willing to risk rejection, sometimes over and over again. Sounds shitty, amirite? By the way, I have daughters, and I have told them that if they meet a boy they fancy, don’t wait to be asked, men can be pretty fkn oblivious, and if you wait to be asked, you are limited to the boys that are both attracted to you and have the balls to ask you.
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You learn to ask for what you want. Skillful flirting is a way to find out what the likely answer is long before you actually ask. But this is the assertive bit. You have to say what you want.
Here’s the most important thing to remember, and this transformed my dating life. Rejection is not an objective assessment of your worth as a man. Rejection means only that you and the woman you approached, for whatever reason, were not compatible at that time.
Learn to be charming, and I don’t just mean women. When you have a conversation, give the person your full attention. Show that you are interested in them as a person, in their opinions, in their experiences. Not too creepy though, not interrogating them. This will take practice, if you don’t already know how to do it. Remember their names. Remember the important people in their lives that they tell you about. If you remember the next time you see them, that will impress them that you really are interested in them.
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Have good hygiene. Be clean, well groomed, clean teeth, fresh breath, smell nice, nicely groomed clean hair. If you are going to sport facial hair, it should be well groomed, but maybe pass on making it weird, if you really want to date.
Some odds and ends on this. Be kind, be compassionate. You probably don’t want to be with a woman that lacks those qualities, so don’t be a dick, yourself. Another thing is that, ultimately both women and men want to feel like they are special to someone. Making her feel special means you are interested in her as a person, making her feel loved and appreciated is important to you. There is nothing quite like the feeling of seeing a loved one’s face light up with a big smile when they see you.
If you approach a woman that doesn’t know you from Adam, bruh, that’s creepy. Here’s the deal. In her mind, if you do a cold approach, on the street, in a bar, on a bus, you are just going for her face and her body, which she has no control over. In her mind, to you she is an object, dehumanized, and that’s the first step towards rape. If you are movie-star good looking, that might work sometimes. You need to first make her acquaintance, get to know her, and let her get to know you, as a person first.
This is perhaps the most important piece. You cannot take it personally if she rejects your advance. Dude, have enough confidence in yourself not to take a woman’s rejection as an objective statement of your worth as a man. You review the interaction, you think about what you might have done differently, and you learn from the experience. And they you try again with someone else.
Hmm. This question was asked quite some time ago, but it just showed up on my feed. I see some answers I agree with, and some that are just plain stupid.
Now, given today’s culture, I can suggest you approach it as a video game. You need all the powerups you can get.
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Dress well. Maybe the chick you’re after is into stained techie t-shirts with holes in it, but that’s not the way to place your bets. Wear clothes that fit well, shirt with a collar, pants with a belt, clean shoes.
The above point means you need to get your ass into places where women are, and where it would be normal to have casual conversations and make acquaintance. Not online. In person. Pick some activity you might enjoy that will include a variety of people. Join hiking groups. Take adult classes. Play in a coed team sports league. You have something built-in to talk about, the activity. In my case, two such activities were meditation classes, and partner dance classes.
There was a time where the man was expected to persist in pursuit of his lady love in the face of rejection. That stopped being relevant when it stopped being expected for a woman to be a virgin when she got married, when women were permitted to hold down paying jobs, and handle their own finances. In other words, when women got most of freedoms afforded to men (fk you, forced-birthers). Now, if you persist in the face of rejection, that means you are unable to respect her wishes, you do not respect her, and you are being a bit rapey. Remember the rule of enthusiastic consent. Hell, yes! or Fuck no!