In our society, men are often told not to be too forward or too pushy when approaching women and asking them out. Indeed, being too forceful and too direct with a woman who barely knows you or doesn’t know you at all will make her feel uncomfortable or “cornered” and very little good will come out of the pressure that she is feeling when you express an interest in her or ask her to go out with you. Thus, coming up to a woman with whom you had very little contact before and telling her “I really like you, and I would love to go out with you” is too much of a good thing, unless of course that girl likes you just as much as you like her or more, which is quite uncommon.
On the other hand, being too casual about asking a woman out and making it look like it means nothing to you is also a bad idea, as it takes all the fun and romance out of the process. Recently, I witnessed an incident, where this guy asked out a grocery store cashier in the following way, after talking to her for about two minutes: “Hey, wanna grab some dinner later?” The girl declined his invitation even though she told him just a few moments earlier that she didn’t have any specific plans for that evening. I will not suggest that I know the exact reason why she didn’t want to go out with him, but the overly non-chalant way that he asked her out in was clearly not attractive or in any way romantic. In fact, I think I noticed one or two people standing nearby who actually rolled their eyes when they heard that conversation.
There is nothing particularly terrible in what that guy siad, but there is something wrong with using the word “grab” in the context of asking a girl out. It’s way too casual. It almost suggests that the guy doesn’t care at all if the girl he is asking out joins him or not. Generally, if a woman wants to have romance in her life, she wants to know that she is not in the guy’s “whatever” category. She wants to be asked out; not being asked to “grab” a drink or “grab” dinner. A much better way to ask a girl out in that same situation with the cashier would be “Hey, I know this little café. Join me tonight for dinner if you are available. They have great food and/or wine” or something like that.
In an attempt to cure themselves of desperation and neediness, guys have been trained all too often to show that they are a challenge, that they don’t care, that they don’t need a woman in order to be happy and that they keep things “light”, but this is not necessary and is actually counterproductive if taken to an extreme. A healthy amount of interest and attention without going overboard is flattering to a woman who is single, available, interested and who is attracted to you. This kind of healthy, confident initiative makes the guy showing that attention to a woman come across as the “real man.” If, on the other hand, the girl is not interested, no matter what the man’s approach is, it’s not going to make her more interested in him.
Surely, there are women out there who don’t like any kind of attention from men. Some of them just got out of a terrible relationship, and the last thing they want now is meeting another guy who is going to create possible complications and “drama” in their life again. Others have had their fair share of stalkers and are extra careful and overly skeptical about meeting men now, and some might prefer women over men. But, you shouldn’t be dating those women anyway, so if they don’t appreciate a flattering attention from you, consider it great news – you are saving yourself a lot of time and trouble by finding it out early on.
I also discuss the above “grabbing dinner” incident in my article about why being presumptive is not attractive to women.