How long should I pursue a woman before I give up?
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Duncan writes, “I am completely fascinated by a woman who is much older than me. Even though she is old enough to be my mother, she is very attractive and has this seductive quality that can drive men nuts. She is single and despite her charm I doubt if she has any man chasing her. Ours is a small community and most of the people know each other. There aren’t any bars or nightclubs for singles to hang out so as far as I can tell, she is probably not having a lot of luck with guys. In any case, there are hardly any men in her age bracket who are single. I am sure that she still thinks of her as an attractive woman but the reality is that she is not as hot as she used to be in her 30s and 40s. The disappointing part is that despite my best efforts in pursuing her, she has resisted me. The harder it becomes, the more motivated I get to pursue her, but when does it become the case that I’m chasing my tail? It’s been so long now - I’m starting to wonder if she’s just seeing how long I’ll remain interested - just drip feeding me enough to keep me coming back for more. I personally think the next 3 to 6 months will make or break this. What do you advise?”
You raise a very interesting possibility but this is something we often get wrong. In my opinion the world is divided into three types of people: hopelessly romantic, moderate sexual appetite, and asexuals.
I would like to think that all teenagers or young people are always in the mood and will have sex whenever they can, but that clearly isn’t the case. I would also like to think widows, divorced, and older people will welcome any opportunity for sex — especially with someone younger — but that is not the case either.
What I have concluded is that sexual appetite is not related to age or relationship status; some people just are very sexual and others are not.
With that said, yes, she is much older and lot less desirable and has much fewer opportunities for running into men with potential for sex. In addition to that, in her age bracket there are generally fewer single men and those there are typically prefer younger women. At the same time, she is exactly at the age that women go through menopause, a very difficult time for women in the sense that the hormonal changes upset everything, all the way from mood swings to very low libido. My conclusion is that you would like to believe that a mature woman with so few options for great sex would never deny a handsome, young stud from making love to her with all the passion that has accumulated over the years for her, the reality is that people are complex and their sexual needs/preferences are even more complicated.
I understand your frustration and that is why trying indefinitely is a bad idea. I totally support your plan that if something does not happen during the next 6 months, you should stop pursuing her because I know this must be emotionally draining. If someone is rejecting you consistently for that long, you have to back off because at that point it almost sounds like stalking and harassment. I know that we guys try to put a happy face on even an abject failure, but you will agree with me that every time we are rejected (even if the possibility was remote) it hurts.
