Wise Guys: Can't Women Ask Men Out?

photo by rick

Advice from three of our guy friends. This week a straight woman asks, “Why do some guys get freaked out if a woman asks them out, and act like she’s desperate? Is it because they feel like they have to say yes? Or does it actually make a woman seem less attractive to some guys, if she’s playing the opposite of hard-to-get? Do guys make assumptions about what a woman is like, based on the fact that she asks him out?

wiseguy_benStraight Married Guy (Ben): I would guess one of two things is happening here. Either you’re dealing with a really immature guy — a guy who doesn’t have a lot of experience with dating or who isn’t all that confident in himself — or you’re dealing with a guy who just doesn’t want to go out with you. Either way, there’s a strategy here for easily figuring out how a guy is going to react before you ask him out. It’s called “flirting.” Start slow, toss an innuendo here, a very casual touch there. If he returns the flirt then start ramping it up. Really, everyone – man or woman – should have a pretty clear idea what the answer is to “Will you go out with me?” before you even ask it. You’ve achieved “expert” flirting status when you can get your mark to ask you out first. Saves you money on the date while you decide whether he’s good enough for you.

Gay Commited Guy (Bradford Shellhammer): Yes, some men like women who are quiet, who play the part of the damsel in distress. They like the power struggle. For those guys I imagine it could be a turn-off. But for every one of those guys, the ones intimidated by strong and direct women, I bet there are even more who’d be welcome to women making the first move, being the pursuer. Yes, guys — hell, everyone — makes assumptions about people based on first impressions. Nothing new there. But women should be more aggressive with dating and asking guys out. I think it would, in the long run, save them a lot of headache.

anonymous_suitStraight Single Guy (Max): I like a girl who is hard to get. Us dudes like the thrill of the hunt and the time during which we don’t know if anything is going to happen. When a girl asks me out it is (most of the time) a thrill, but quite different from working hard for a lady, and eventually getting what you want. Suddenly, you realize that you are the hunted and this can
be either amusing and awesome, or a frightening realization that your game ain’t up to snuff. Personally, I’m quite intrigued by any girl who has the guts to ask me out. A girl who knows what she wants is a good thing. For all ladies considering such moves, however, I will point to this question as a good indication for the risks involved. We CAN get freaked out and you CAN look desperate if you do this in the wrong manner. If you ask a guy out, give him options. Let him feel a bit of power by picking the location, time or whatever. Just don’t walk up to him and tell him to take you out this Saturday and that you love sushi. Even if you’re a total babe, this is a strange move and will spook most men.

Our “wise guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week’s Straight Married Guy is Ben, a writer and artist living in Los Angeles who runs AdultParlorGames.com; our Gay Guy is fellow SUN blogger Bradford Shellhammer, the creative director of fabulis and a New York Times featured decorator; and our Single Straight Guy, Max, is a recent college grad in New England. To ask the guys your own question, click here.

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29 Comments on "Wise Guys: Can't Women Ask Men Out?"

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1 year 7 months ago

I think this day and age women have to take more initiative. Guys are too scared to ask women out for fear of rejection; they don’t want their ego bruised. I have asked a few guys out and they have not had any problems with it. Granted this has only been two guys including The guy I am dating now. I asked him out because he was trying to hint at it, but never made the follow through. We have been dating for 2.5 months now. Ever since then he started asking me out–now it is just implied that we will see each other.

Girls really have to fight for what they want. This can be done with being feminine. I typically ask a guy where his favorite place is and when he tells me I say “I have never been there, I would like to go sometime” (even if I have been there hehe). This leaves a direct invitation for the guy to ask me out. Sometimes you just have to put yourself out there and go for it!!

2 years 10 months ago

I guess that the tide IS turning if fewer men are approaching women these days.Naybe men got fed up with this and tried to obtain more vslue snd respect. I hope that this is the case.

3 years 3 months ago

I have asked A guy out and although he said no because he was in a relationship he seemed to be genuinely flattered. I can’t believe how far behind we are in this subject. I thought I would find a lot more positive articles on Internet about women asking men out but I haven’t seen that many. I agree with some of the previous posts that I’m not so into the man chasing woman only nor do I consider myself overtly aggressive. This may sound a little out there but I went to be in a mutual type of relationship where it’s more equal. I don’t want to feel like I’m being chased because usually when someone is being chased, they are running away.

3 years 8 months ago

I have never asked a guy out before but I have made the first move with a guy. He reciprocated but then quickly backed off and I never heard from him again. I found it interesting that most women commenting here have found that when they have asked guys out it has had negative results and this was obviously my experience too but I always felt it was because I had misread the signs but perhaps he was intimidated by me taking control. Who knows? I have also found that men do indeed tend to pursue you harder when you either are or act uninterested. I am rarely flirty or friendly with men and I tend to keep my barriers up but I have noticed that men pursue me far more ferociously than every other woman I know and so perhaps this is because some men enjoy the challenge of the chase. I do believe though that the bigger problem lies with the reaction of men than the issue of women being able to ask men out, probably because notions of masculinity are so deeply entrenched within society. If a man feels emasculated by a woman asking him out then of course he is going to be less interested in her and that is more difficult for a man to get over than it is for a woman to risk coming across as desperate. Men are just very sensitive about their masculinity because it is less defined today. I personally wouldn’t ask a guy out because I believe he wouldn’t take me seriously as a potential partner, however, if I was friends with a guy and there was a strong indication that he liked me and he was on the shy side I probably would confess my feelings to him but I wouldn’t ask him out. I would leave that up to him.

James S
3 years 8 months ago

I was looking up a similar topic to this but I found this thread, which I’ve found interesting. This issue affects me as a guy as well as my sister too so I feel inclined to post a response on here, despite the thread being 2 years old.

In very simple terms I think that the root of many men responding negatively to women who approach men comes down to two things; sexism and pride. This form of sexism starts at birth in blue being for boys and pink being for girls. As a person of each sex (and ultimately gender) grows older their enviroments already start to signal what are considered appropriate behaviors, and which ones aren’t. I do believe there are some inherent differences in the mentality of how each sex behaves from a biological standpoint, but I still believe that the majority of these stem from gradual gender conditioning while growing up. Note: Let us not forget that gender and sex are two different things.

I’m going to post the following and this is coming from a very introverted (and sometimes shy) guy. I have an attractive sister (who’s definitely not a loser) who has not had a boyfriend for 8 years now. The few boyfriends that she did have in the past did pursue her, only to have those relationships fall apart very quickly because they ended up either being outright jerks, control freaks or they got bored after the chase ended and went on to bigger and better challenges. There was an exception with one guy who did pursue her, he was very clean cut and came from a well known conservative family. He even asked for my father’s hand in marriage. They were with each other for about 6 months before they got engaged. They stayed together for nearly another year after that but once the engagement took place he started treating her like a jerk. He eventually cheated on her with the girl he is now married to. After this she decided to take matters into her own hands and started attempting to become the one to initiate contact with guys. Unfortunately she usually got blown off and this strategy didn’t work for her either. She tried online dating but the guys that initiated contact with her usually would just disappear, perhaps after their aggressive ‘alphamailing’ landed them a ‘bigger hit’. I don’t know but there was a pattern with that situation occuring over and over again regardless of whether the site was eharmony, match or a nonpaying site. Her attempts at initiating contact online fell flat as well. My sister’s best friend, whom also happens to be very attractive, is in the same boat as my sister and she has been dateless for a long time as well.

I’ll describe my own situation briefly here as well. I actually have little problem conversing and even initiating it when it comes to both men and women (I’m straight) but I’ve had my own difficulies as well when it comes to dating. Personally I prefer a bit more mutuality when it comes to the initial part of trying to get a date rather than pursuing a woman, or having a woman pursue me. I’m one of those guys who prefers to already be reasonably close to a woman by some other means outside of dating before actually dating her. I’m not into the blind approach or pursuit like some other guys are, and it’s not because of a lack of confidence/self esteem but because of a lack of motivation. It’s not because I find no value or attraction in any particular woman but rather the opposite; I find that my attraction for certain women completely depends on already knowing something about the woman to begin with, along with her making some type of effort herself. Maybe not all guys will agree with me and I’ll be billed as making up excuses to hide my insecurities, but in the end I know myself and my motivations for what I do (and don’t do) better than anybody that would attempt to criticise my above statements and preferences.

I think that there are two particular things that make dating difficult for both sexes involved like I’d mentioned above: Sexism, due to social gender constructs and Pride. Let’s face it, most of us want to be reasonably accepted and respected by our peers and we do not want to become individual targets. The default mindset that most men have is to be seen as ‘real men’ by others. Men are still held to being men more than women are held to being women, even today. Even though I truly believe that many men would prefer dating and finding one’s mate to be easier (at least the men with better intentions), the power of how we want to be perceived by others is very strong. We see this all of the time in a society full of facades and many people do not always do what they really want to due to the grip of how we want to be perceived by others, at least in our own minds. There is more to this than just sexism along with our egos/pride however and many women to a far extent are responsible for this dating chaos as well.

In the end the only answer to the chaos involved in dating will be the members of both sexes maturing and mentally evolving over the future years. I do believe that men and women have different ways of apprehending various situations regardless of individual personality traits. Nevertheless I still believe that the dating ritual could be more mutual and lead to more fruitful relationships if more people stopped seeing themselves as guys/girls foremost whom just happen to be John/Jane Does, and instead started seeing themselves as John/Jane Does foremost whom just happen to be guys/girls. We all have our individual preferences regardless of the sex we were born as, and this concept does not change when it comes to dating. Perhaps to some guys it is more important on how they got involved with their woman but some of us guys find that actually being with that certain woman is more important than how we got there. To expect a society full of so many different archetypes and personalities to positively respond to a certain set of rigid dating rules is an untenable thought to me.