n my other line of work, I get questions from women constantly to the effect of, “How can I make this guy like me?” You might be thinking “Well, gosh, that’s dumb. Obviously you can’t ‘make’ someone like you any more than you can ‘make’ yourself into an NFL player.” If you think about it, though, it makes a little sense from their perspective. It’s typically the women who get pursued. They’re “liked” by the guys, and it’s up to them to accept or decline their advances. When the opposite happens, it’s understandable that they don’t know what to do. For a lot of women, it’s uncharted territory, and even for the ones who find it happening often, there’s not a lot of useful advice out there for them (mostly because in that situation, there’s no advice to be given, period).
What’s funnier is that men have their own version of the same thing, only phrased differently. As men, we tend to come at it from the other angle and ask, “How do I know when to back off?” In a way, it’s even less sensible than the female version. The women are at least being proactive and looking for a course of action they can take to make things turn out in their favor. On the other hand, men are basically asking at what precise point their pursuit becomes a waste of time, as though time spent courting a woman that doesn’t end in sex is an objective “waste.”

We ask this question because we see our interactions with women as a linear process. Once we meet a woman we like, we expect that the more we “give,” the more we “get.” We show interest, she reciprocates. We spend resources on her, including time and money, and we expect further commitment and intimacy. We spend even further resources and finally make the overture of engagement, and we expect acceptance. When it works out that way, all is right with the world. We invest both physically and emotionally, and we get a return on it. Even when relationships don’t work out, it’s a case of one or both parties recognizing what they see as a bad investment.

What baffles men is when things never get off the ground to start with. They’ll usually meet a woman, develop a small rapport, and then go about the courtship process. The problem is, they get stonewalled. The woman might find them pleasant enough as an acquaintance, but isn't interested in dating. That’s when as men we’ll start to pour it in thicker and thicker. We’re conditioned to believe that investment equals rewards, so we figure that if we’re not getting enough output, we just need more input. That’s why you’ll see guys ask the same woman out time and time again, or lavish gifts on a woman who’s never so much as agreed to a date. They'll keep going until they reach what they believe to be her threshold for “caving in,” not realizing that a woman’s acceptance of your investment is entirely contingent on her own investment in you.

So, when do you know when to back off? The first time she genuinely, explicitly rejects you, that’s when. No one can blame you for making the overture, but she’s not under any obligation to accept it, either. Sure, now might not be a good time for a particular girl due to any number of circumstances, but she’ll let you know that. There’s a difference between “thanks for the offer, but I can’t this weekend” and “thanks, but I’m not interested.” Now, is there such a thing as a woman who’ll meter her affection based on how much and how hard you pursue her? Yes, but those women are looking to take advantage of the kind of man who lays way too much out there to begin with. Don't be that kind of guy. What you'll be hard-pressed to find is a woman with genuine intentions who forces a man to unlock some kind of secret combination before she agrees to reciprocate. It’s just not how normal people work.
In fact, it not only behooves you to know when you've worn out your welcome, but to stay on good terms with her as well. Male-female relations don’t have to be a zero-sum game. Just because she doesn't want to date you doesn’t mean she considers you objectively un-dateable as a human being. She could have lady friends, for instance, that she might see you matching up with perfectly. What will jeopardize that is if you, instead of taking the hint early, continue to press, pursue and invest to the point of frustration. She sees you as the kind of guy who won’t take no for an answer, and you end up with a chip on your shoulder about the female gender as a whole. When that happens, only one of you is right, and it ain't you.

I tell guys the same thing I tell girls: If she wants to be with you, she’ll make it happen. If she doesn’t, it’ll be obvious sooner rather than later.