Do Men Like Mystery?

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Is it okay to ask a guy out? I have heard mixed answers on this subject, some guys like it, but others find get turned off. According to the book “He’s Just Not That Into You,” women should not ask a guy out, because the guy misses out on the chase and the woman is not as much of a challenge. There’s a guy who I’m interested in getting to know better, but I don’t get to see him often. We e-mail once in a while, but I wonder what’s wrong with me asking him to meet for a drink or something? It it too pushy? My girlfriends tell me that I shouldn’t do anything and I should just let him ask me out if he’s interested. What’s your take on this?

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ORIGINAL ANSWER:


Here’s what I believe. If a man is interested and is confident enough, he’ll ask you out. Now, many times are totally clueless as to when a woman is flirting with them. So, our job is to give as many green lights as possible so that he’s aware of your interest and knows the risk of rejection is minimal.

I don’t think asking a man out makes a woman look pushy. I think it makes her look anxious. She’s revealing to the man that she’s interested, which thereby takes away the “chase” so to speak. And, yes, guys enjoy the chase. A slight chase. Why? Because we all want what we think we can’t have.

UPDATED ANSWER – FEBRUARY, 2025:


Let me state, for the record, that I don’t think women should ask men out. Maybe I’m just a throw back, or an Old, but there are just some traditions that I think need to stay in tact. Why do I believe men should ask women out? Because I think people become easily complacent when things are handed to them. When a woman asks a man out and the man says yes, we don’t lose interest, we gain interest. In my opinion, that’s not how it works with most men.

I read a story recently about a woman who met a guy at a party. She and the man, in her opinion, flirted for a good deal of time. Yet the guy never asked for her number. So, at the end of the night, she ran in to the man and asked him “if he wanted her number or what?” Like most men in that situation, he took the number. He called her a couple days later and they went out. The man proceeded to act, well, not so great. He answered his phone, sent texts, frequently turned his attention to the TV. He didn’t exactly display the most stellar of manners. The woman still went home with them man, which also turned out to be a comedy of errors. Her hopes of salvaging the night were dashed when the guy turned out to be, in her opinion, a pretty awful lover.

My take on this situation was that the guy already knew, because she basically egged him in to taking her number, that she was interested. He had already dismissed her by not asking for her number. That she would further pursue him told him he could act any way he liked and get away with it. And he was right. The date should have ended after the first cocktail or appetizer. Instead it progressed to his bedroom. He was rewarded for his bad behavior. That’s what women need to remember when they convince themselves that they should try to “salvage” a night out and get some sort of return on investment. And FYI..men? Same goes for you. Many of you like to talk about how you’ll go on a date with a woman who act inappropriately, but you’ll “try to get your money’s worth” by getting her to blow you. I realize that you don’t care if she gets some smug satisfaction for that.Just keep in mind that when you do this, you’re telling her that her behavior was acceptable and okay. If you don’t like being used for your wallet, stop rewarding women with little affirmations like allowing her to go down on you. Because if she’s clueless enough to be texting her BFF on a date, she’s clueless enough to think that you’re having sex with her because you find her attractive and not because she just happens to be there. One way to stop bad behavior is to not reward it.

Okay..back to the topic…women asking men out.

So, the woman from the scenario I just mentioned pretty much set herself up, in my mind. She made not only her interest known, but her willingness to overlook possible questionable behavior. This guy went in to the date likely believing that he could do whatever he wanted and this woman would still be interested. He also took a lazy approach to the overall date. He didn’t appear to even try to make a good impression. Why? Because he knew the woman was attracted to him. I don’t think women make the same assumptions when a man asks them out. I don’t believe we assume that we’re “in” just because a man asked for our number.

Men have been doing it for so long that, while they enjoy the change, they can’t fully assume the position of the one being pursued. When they ask a woman out, they know they do it because they’re interested. So they assume the woman is interested since she took the initiative and invited him for a drink. The difference is that a woman would still try to impress the man. The man just gets too comfortable too soon or doesn’t make as much effort as when he did the asking out. (YMMV on this one. Just my opinion. )

To bottom line it: I think most men enjoy not just the sense of challenge that asking a woman out provides, but also find the “mystery” of whether or not she’ll sleep with him arousing. Ask a guy out and, even if you don’t know if you if you want to have sex with him (please…we know in the first couple minutes of conversation), and he knows. He assumes eventual sex is a given.

Game over.