Global Classroom Certifications

When Persistence is Perturbing

by Don Polsy

Hi Susan,

A topic that has proved confusing for me is pursuit and persistence in dating. There’s so much conflicting information out there. 

Basically, as a guy, I feel that it is my duty to do the approaching. As much as I’d like women to be more forward in their interest, I just don’t really see it happening. I usually have to do all the legwork, and I don’t mind, but things get confusing.

I hear so much about how women love to be pursued, but it seems the line between pursuit and stalking, and confidence and desperation, is very thin, with said line moving depending on the girl’s preferences.

In an era of the Principle of Least Interest, I hear one side (namely the Red Pill) saying to act disinterested and let the women come to you, while other sides say to keep trying in a pleasant confident manner and you might just win her over.

Some women claim that they’d never date anyone if a guy didn’t ask several times and other women say that asking for a date more than once is too much.

It’s enough to make a guy’s head spin, and the last thing I want is a restraining order.

I recently read a forum post from one woman on a dating site who admitted to rejecting all the guys who ask her out in favor of chatting up one guy who, although admittedly friendly, hasn’t bothered to ask her out yet. I don’t know whether to think she’s one irregular case or whether she’s typical of most women.

I can understand that woman like mystery and the will he-won’t he feelings, but how much interest or disinterest can one guy show? It’s a lot of effort for something that really shouldn’t have to be so difficult.

Do women, in general, want to pursue the guy they desire and win him over, or do they want to be pursued and be won over?

Thanks,

Tyler

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There’s a lot to unpack here, so let me address your thoughts one by one.

As much as I’d like women to be more forward in their interest, I just don’t really see it happening.

There is no one-size-fits-all answer to this. Certainly, more women take the initiative today than they did two generations ago. When you think about it, it seems pretty obvious that some women are more likely to be assertive with men than others based on their personality traits and what they’re after. What might predict how assertive a woman is in mating?

  • preference for non-traditional gender roles
  • extraversion
  • willingness to take risks or even gravitation to risk
  • high degree of confidence in success, perhaps reflecting better odds associated with short-term mating

I wrote a post recently about how a reader found a boyfriend on Tinder. Jenna had a strong preference for a traditional dating arrangement, so she adopted a deliberate strategy of only responding to matches who reached out to her first. If a match had not initiated conversation within four days, she unmatched him. Out of her 55 initial matches, 33% (18 guys) had not gotten in touch during that time. She also unmatched any guy who gave off even a hint of using Tinder to hook up.

In my experience, there are a lot more women like Jenna than women who possess the traits above. It depends on what kind of girl you’re looking for.

It seems the line between pursuit and stalking, and confidence and desperation, is very thin, with said line moving depending on the girl’s preferences.

While I agree there are individual preferences among women (see above), I don’t believe the line is actually thin at all. Even women who are willing to pursue a guy may still expect to be approached often themselves.

No woman wants to feel stalked by a desperate male. (Note: these two go hand in hand.) Women have very good reasons for being wary of male strangers and strong incentives to be choosy in their selection of potential sexual partners. Needless to say, desperation is universally unattractive to both sexes, as it conveys extremely low mating value.

I hear one side (namely the Red Pill) saying to act disinterested and let the women come to you, while other sides say to keep trying in a pleasant confident manner and you might just win her over.

Acting disinterested, or engaging in push-pull, can only work if the woman finds you attractive in the first place. This is why PUAs rely on the neg so heavily – they create false interest by targeting the woman’s self-esteem in an attempt to make her feel unworthy of their attention. Then when they pull away, she is supposed to fret and pursue. Needless to say, this can only work with a woman who has a very poor sense of self-worth. Sociopaths target these women to get laid.

The Principle of Least Interest is real, and can only be interrupted when one party risks showing interest. Most women are happy to flirt and encourage men they like, but the approach and ask will usually be up to you.

Both men and women are drawn to those who are not easily obtainable. We are attracted to those who have options. Women like mystery in the sense that it can indicate a guy has options, but we’re very astute about what guys those are likely to be. We have well-honed antennae for detecting impostors.

Some women claim that they’d never date anyone if a guy didn’t ask several times and other women say that asking for a date more than once is too much.

Really? Not even The Rules suggests making a guy ask several times. I’ve never known of a woman who repeatedly declined a guy she wanted to go out with. The risk of his losing interest is just too great.

If a woman is attracted to you and wants to go on a date, she will make sure you know this. If you ask once and she is unavailable but is interested, she will suggest right then and there that she would like to take a rain check. She may even suggest an alternative time.

If she says “no, thank you” or declines your offer without encouraging you to try again, she is not interested. Any further attempts on your part will suggest an inability to read social cues and behave appropriately. Numerous attempts to get her to go out with you will rightly be perceived as stalker-ish.

By the way, lots of times women just don’t want to be approached, period. They’re in a relationship, they want alone time, they’ve just been through a breakup, whatever. Many rejections are not personal, because the woman doesn’t even get to the point where she’s evaluating you as a candidate.

Women generally don’t feel that a guy’s asking for a date once is unreasonable if there has been preliminary social contact, preferably with flirting. Most women will feel uncomfortable or even alarmed being approached for a date by a stranger. You could be a serial killer for all she knows. A very hot guy in a bar once asked me to go scuba diving the next day and while I was tempted, I thought it was way too risky. It felt like a potential setup for a murder mystery! So it’s important to proceed in a way that shows you are a stand-up guy.

There are women who reject men with little sensitivity. Those women are jerks. If a woman shuts you down rudely, console yourself with the knowledge that you’ve dodged a bullet.

Do women, in general, want to pursue the guy they desire and win him over, or do they want to be pursued and be won over?

Keeping in mind that women differ in their preferences, I would say the following is true on average:

  1. Women do not want to do the work of pursuing. We select from among the men we believe we can attract or those who are clearly interested.
  2. Women do not want to be won over for a first date. We want you to confidently ask once. If we are interested, we will agree. If we decline your invitation, please accept that and move on. Persistence at this point is an imposition and an annoyance.
  3. Women do want to be won over for romance during a period of getting to know one another. They also want to win you over in the same way. This hinges on the attraction being mutual, which was the prerequisite for that first date.

Susan

P.S. Never use a strategy of starting out as friends and hoping to win her over gradually. Women disrespect this and find it sneaky. If you like a girl, sack up and say so.

HUSsies, do you agree with my advice? What would you add? How do you suggest Tyler proceeds when he is attracted to a woman?