Approach a Potential Date: Etiquette for Men over 50

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Women over 50, like women of any age, generally appreciate an admiring glance, but make sure you know the difference between an admiring glance and a leer. Don’t even think of any other gesture when you look at someone. No hand gestures, no mouth gestures, no finger clicking — nothing but the frank stare of appreciation and a slight or even big smile.

You need to convince a woman that you think she’s attractive without coming across as a threat. Men often don’t realize the level of fear many women have about meeting a stranger, so show interest while at the same time showing that you’re a good, friendly guy and that she doesn’t have to be afraid of you.

How do you do that? By approaching slowly and carefully and saying something kind and friendly. After she acknowledges your several-second stare from afar, you have to dial down the intensity by walking over, smiling, and keeping your eyes focused above her collarbone. You don’t want her to feel like a piece of meat; you want her to feel admired in a nice way.

When you walk over, approach in a gentlemanly fashion. Don’t interrupt her if she’s in the middle of a conversation. Wait for a break in the conversation and then introduce yourself, and be sure you have a follow-up line to avoid an awkward silence after you’ve said hello.

Your opening line should say something about why you noticed her, such as her laugh, her smile, her overall attractiveness, her clothes, her style, or the way she talks with her friends. In other words, something nice that has nothing to do with her chest, her butt, or even her lips (even if that’s what you did notice).

For example, you could say, “I’m drinking pale ale too. Can I buy you one?” or “You seem to be having a lot of fun here. I wondered what you were all laughing so much about.”

If you can avoid it, don’t have a drink in your hand. You want her to believe that your interest in her is genuine rather than the result of moderate to extreme intoxication.

If you can find something in common as soon as possible, that will reduce her fear ratio. Perhaps you both work in the same building or both know the wedding party at a wedding. Or you can just straight out say, “Tell me a bit about yourself,” and search for common networks or neighborhood- or work-related things that may be mutually interesting.

Men are often expected to make the first move, so you have that going for you. At the same time, there is such a thing as being too forward or aggressive, so you have to moderate your approach so it feels comfortable to both of you.

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