I Am Too Flirtatious. What Are The Boundaries?

Dear Hal,
I am a “young” 76-year-old who has been single for just over 4 years now following my wife’s passing. I am fortunate to have many friends who often host parties in addition to the get-togethers that are organized by our building complex. I attend almost all of these events and I enjoy “flirting” with the many women who attend. However, I have been told that, at times, I am too flirtatious. What are the boundaries? I usually just talk up women, tell some jokes (never “dirty,” but I admit, they are sometimes “saucy”). I certainly don’t do anything physical (except for an occasional hand-hold or arm around a waist). Do you have any kind of guidelines that you use?
Flirty in Florida
Dear Flirty,
My first question is, who said you were too “flirtatious?” Is it a woman who would like you to confine your flirtations to her? (And of course, she is right, if you have settled on a particular lady.) But that doesn’t seem to be the case. Flirting is certainly flattering to most women and of course, by its very nature, in the situation you describe, there will be more than one woman to whom you will pay attention. After all, if you have made more than one woman feel admired, then you have done a good deed for their self-esteem. But this gets tricky if your intention is to bed one of these women. Could you be seen as “all talk and no action” in the minds of some women who do want “more?” Additionally, if you walk off with one, you run the risk of leaving the others with whom you flirted a bit put off. This may have repercussions at the next party. I wish I could give you some rules, but there are none in today’s new relationship culture. But at your next gathering, slow down a bit and be more restrictive in the number of women with whom you flirt. Assess the feedback you get at that point and re-evaluate. But whatever you do, don’t stop having a good time and putting yourself out there. You’re a young guy, so feel good about yourself.


  1. Ben

    I do think that flirting *too* much could be a problem. Making known that you’re available for sex (if in fact you are) can lead to opportunities, but you have to be discriminating. A man can come across as “willing to saying anything to anyone” in which case giving a complement loses its value for the recipient. Sex partners want to feel special, like you are really appreciating something interesting that you’ve noticed about them, that makes that person unique and intriguing, even if it doesn’t lead to a relationship.

    Alternatively, if you’re not seeking sex, that’s all the more reason not to seem like you are!

    So I might try not putting my arm around anyone for two or three weeks, just to see what the reaction is, because “too flirty” might be a euphemism for “invading my personal space more than I really like”. Also, women can tell if you’re taking advantage of the social situation to get a private thrill, and they don’t like that.

    So you know: I’m in the “just curious” category, married, gay, 49 years old. So what do I know! Except this: I actually enjoy physicality and flirting in a party setting, but I really do think less of people who go overboard and “take liberties”. I had one friend who was “too flirtatious” with me. He would practically proposition me every time we were in the same place. That was amusing, but not in a way that made me like him, and I was never able to relax and enjoy his company.

  2. Nancy Woods

    love your website, Hal. very interesting to women, also

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