We guys are told to take the lead, go forth boldly and ask women out. We’re expected to follow through and follow up, expressing our interest with post-date calls and invitations for future outings.

But if you’re the type of guy who breezes past unanswered emails, curt phone conversations, and slammed doors in the single-minded quest for the love of your life, you need to hear a message loud and clear. And the message is this: Being persistent is fine (up to a point, anyway), but you have to know when to pull the plug before persistence turns into self-delusion — and self-delusion turns (in the eyes of your intended) into hassling a stranger. So how can you keep yourself from crossing this all-important line? Here are few tips:

Remember, the entertainment world is different from the real world. Hollywood comedies and TV sitcoms are rife with dubious yet inexplicably effective romantic maneuvers. This has planted the subliminal message in the minds of perhaps millions of singles that you can get anything (or anyone) you want, if only you’re willing to try hard enough. It’s pretty to think so, but it’s not true.
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Pay attention to her signals. As Myles Reed Jr., author of Fishing for Love on the Net, says, “Uncontrolled optimism for the relationship that might be is no excuse for plowing through a woman’s persistent messages that she is not interested. You might be pulling a Bruce Banner; even though he was well-intentioned when he turned into the Hulk, he still freaked out a lot of people.” In other words, if the object of your interest has made it clear that she doesn’t reciprocate your affection, no amount of well-meaning shenanigans will make her change her mind. Stop, already!

Bounce the situation off your friends and see what they think about it. Usually, the people who know you best will be the first to notice when you’re sliding off the rails. I remember a close friend talking me out of sending my unfinished novel to a woman I’d been gently spurned by — apparently I was under the illusion that my genius at plot development and characterization would prompt her to think twice about dating me. More likely, she would have glanced at the hefty email attachment, issued an exasperated sigh, and hit the “delete” key.

Be patient. Slow, gentle persistence over a matter of months — say, sending a casual-but-funny email every couple of weeks — is better than embarking on a full-speed, ACME-rocket-powered Wile E. Coyote-style desert chase. “We live in a push-button, get-your-burger-in-30-seconds world,” says Abby, who works for a website dedicated to erotica and has an interesting perspective on this matter. “People have become increasingly impatient, wanting results as soon as they click their mice or retrieve their text messages. Unfortunately, while technology has increased in speed, human behavior hasn’t. People still need to let each other warm up at a human pace.”

Keep it simple. As a rule, anything that smacks of large-scale conspiracy or enormous expenditure — say, hiring 500 fans at Giants Stadium to flip cards that assemble your beloved’s name — will creep a woman out rather than make her swoon into your arms. If you must be persistent, do it in a tasteful, gentle, understated way — think a bouquet of flowers rather than a first-class ticket to Maui.

Ask yourself what you’re really after. George Santayana said it best: “A fanatic is someone who redoubles his effort when he’s forgotten his aim.” If you’re pursuing a woman because you’re piqued by her initial rejection rather than because you feel the two of you might have some genuine chemistry, then your tainted motivation will communicate itself in increasingly needy, inappropriate gestures, like late-night phone calls or daily emails, and you will freak her out. If your interest is sincere, she may (with a little luck) view your persistence in a more forgiving light.

Move on to the next prospect. A few years ago, I gently, sincerely, and tastefully pursued a woman whom I’d met online and had a single promising date with — largely by keeping in touch via the occasional funny email. Her replies kept me interested, and I genuinely felt I had nothing to lose by pressing my case. But when she got engaged, moved to another state and became pregnant (all within a few months), even I had to admit that my efforts had been in vain.

So yes, men, society and the rules of dating expect us to be the pursuers — but please, heed this advice and recognize when enough is enough... before it becomes too much!

Bob Strauss is a freelance writer and children’s book author who lives in New York City. He’s also written the Dinosaur guide on About.com, the online information network owned by the New York Times.