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Why is dating so frustrating and difficult for a guy?

08.06.2025 00:00

Why is dating so frustrating and difficult for a guy?

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.

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.

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.

Hello,hope y'all doin good, i came to Quora to share my strange story , a very weird one , a story when luck smiled at me ,maybe u will enjoy it , let's begin,have fun... A year ago ,I was a real porn addicted(btw I was 18) ,but never had sex before, I don't have a gf I didn't try to find one even ,always thinking to go to find a sex worker but then I just don't , everyday watching different bodies getting fucked and everyday enjoying. One day, I was watching porn, a big ass lady with big boobs ,just after seeing her the image of my female cousin poped in my mind, (let's introduce her : she's 35 years old , very big ass , nice boobs ,not very big but nice,always wearing tight clothes , she's divorced ) and I thought of me fucking her ,I never had sexual desires for her but now I do days went by and when I met her I was so horny ,I couldn't stay with the family cz my penis was clearly erected , I realized this is my first time I get horny for one of my family ,it not illegal in my country.well to make a long story short( if u want details just text me I will tell u 😊),I decided to give her signs that I want to fuck her,finally I decided to have sex and with my cousin , I thought it is the best beggining for me, i started touching her when I came across her in a narrow place , make her feel my hard cock when we hug , I thought it will hard and I will be ashamed but no , I felt nothing and she said nothing , probably she thought it was by mistake,anyways, I decided then to talk with her about sex, waited for her to be alone in a room and talk with her, I confessed everything about me watching porn and addicted..etc,she said it's normal and u are growing up and u must have sex,well at that time I was like whaaat????? Well I didn't control myself and asked her for sex ( horny like I Ve never been before) she said that she will think Abt it ,2 weeka went by then she called me ,telling that she reserved a room in a hotel and we meet tonight ,we met,and bruuhh, sex is great , I mean, I had to find a pirstitue ,what I was waiting for to have such a feeling ????, I will never forget that night, I started kissing her she was kissing hard ,she misses sex so bad , she sucked my dick and swallowed my semen ,I felt I'm in a dream , then when fucked ,her ass was very big and the anus was open ,didn't struggle to get my hard cock inside it , she was obviously missing sex , she was shouting ,fuck me yh fuck me , I go fast after every word until I cum , we did that 3 times , then we went to her pussy , using condoms I fucked her so hard the moans were higher , everything was perfect ,in the end I asked her to lick her body , licked pussy ,ass, boobs,then she sucked my cock until we sleeped ,all I know that she was dirty ,well before even having sex with her I knew she is an open minded woman , and a woman that looks that she donesnt know anything , but she knows everything, but never expected having sex with her ,well she was horny and that helped...but no one of us regretted that sex ever.. We still have sex from time to time ,and I started having sex with sex workers , joining threesomes..etc If u want pics of her text me.

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.

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.

Now, given today’s culture, I can suggest you approach it as a video game. You need all the powerups you can get.

How do I know if I am a bitch? I try to be a nice person but people often jokingly call me a bitch. My family calls me a bitch sometimes too.

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.

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.

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.

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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.

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.

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!

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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.

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.

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?

Why do I feel worthless most of the time?