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When’s the Right Time for Sex? Experts discuss the consequences of not playing by your own dating rules. By Elizabeth Heubeck From the WebMD Archives Whether you’re new to the dating scene, a regular player, or jumping back into the game after a long hiatus, the same questions about dating rules apply: How soon do you lean over for that first kiss? Is it too early for a steamy make-out session? And last — but by no means least — how do you know when the time is right for sex? From Stalemate to Soulmate. According to the singles whom Allen has encountered, boomers generally play by far different dating rules than young, something daters. While you can’t apply a one-size-fits-all response to sexual dating rules regardless of age or experience, professionals who have studied the topic say it is a good idea to develop a set of prudent dating rules – before the big date. By and large, Allen and other relationship experts endorse a cautious approach to the dating rules of sex.