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Online Flirting Finesse


It takes wisdom and courage to flirt online with a senior man because you only get one chance. Flirting online, as in flirting face to face, is all about subtlety.  Too obvious and you’ll seem sleazy. Too humble and he’ll soon be snoring. Here’s how to strike the balance.

1.  Don’t take yourself too seriously. Flirting is by definition playful.

2.  Don’t flirt with a man who doesn’t flirt back, or you’ll suffer the torment of a stand-up comedienne whose audience doesn’t laugh at her jokes.

3.    Be confident. “Self-effacing” and “flirtatious” are mutually exclusive. Senior men have too much life experience to put up with women who lack strength of mind.

4.   Compliment him, but sincerely. False praise works only on shallow men. A worthwhile senior man will be gone before you can repeat, “your devotion to cabbage gardening is incredibly inspiring.”

5.    Don’t let his eagerness to return your flirts throw you off course. Suppress an urge to match his style. Stay with what you know. Don’t try knee-slapping humor if you’re best at dry wit. And pace yourself – – don’t think you have to fill every silence.

6.  Don’t interview. Asking questions is okay, but the conversation should be balanced, reciprocal. Good flirting is anything but superficial. You’re learning about him, and he should want to learn about you, too. If he wants to make it all about him, you’ve got the wrong man.


7.   Never be sexually explicit and don’t allow him to be so. Mild sexual allusion is acceptable – and might be inevitable (he’s a guy) — but in the flirting stage, innuendo can turn rapidly into something you’d rather not deal with.

8.  Don’t gush. Over the top joyousness works well at weddings and fashion shows, but a senior man is generally uncomfortable with perkiness. He’s thinking, “when I introduce her to my kids will she squeal her hello?”

9. Stay alert to negative vibes. If you sense boredom or irritation, extract yourself gracefully and move on. And if negative stuff happens too often, revamp your approach.

10.  Don’t try to speed it up.  Success in flirting with a senior man depends on poise, self assurance, and patience.

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'Online Flirting Finesse' have 15 comments

  1. December 1, 2017 @ 8:52 pm Susan Young

    I am 61 and I have not lost interest in sex. Yes one can still be sexy over 60 but it would be silly to wear a mini skirt or let large breasts hang out of a tank top at any age. Also the tight leggings are not very attractive on any woman who is anything but thin. You don’t have to wear a tent because you are older. Something that shows a little leg or cleavage is good. Even young women can look foolish with too sexy clothing.

    I want a man my age I can relate to not someone that is older and is cold or has lost his fire. A few years younger makes sense because men normally die about 5 years younger than women. I say don’t be afraid to strike up a conversation with a man, if he starts talking back, flirt a little and see where it goes. Don’t be fooled women can be just as sexual as men in their later years. At least I am.

    Personally I don’t think a dirty joke is appropriate in any situation with a woman. I would rather he made a pass at me then tell me a dirty joke. As far as the tab goes; it doesn’t hurt for a man to pay for the first outing, but for crying out loud don’t take her somewhere you cannot afford! Then you can discuss future arrangement for outing expenses. Communicate. Men can be set in their ways just like women. I know that when I go into a serious relationship that I will have to be flexible and give a little and make a few changes but then so will the man.

    If one can let your fear of rejection go, you will open up more and be friendly to the guy waiting with you at the check out counter. Just smile and look around at all the men and see if one catches your eyes and smiles back. Nothing ventured nothing gained. Embrace rejection ladies. It will only be a matter of time before you meet someone. One thing though, if I find someone that seems interested I will give him my number. I figure I may not ever see him again so it is worth the risk of rejection.

  2. September 17, 2017 @ 7:50 am Sienna

    Melvin — It seems to me that you are meeting the wrong ladies! The 60+ women who visit this site are vigorous, dynamic, and sexually alive. They have many interests that go way beyond interacting with their grandchildren.

  3. September 15, 2017 @ 8:05 pm Melvin Kimmons

    I must say these women and their thoughts of an older man is stupid because most men over 60yrs want a younger woman because a woman over 50 is set in her ways and sex isn’t really that important to her she’s all about being a grandmother and that is one of reasons some men in their 50 are 60 become victims of ED and dating a young give them pleasure in being with her and it’s not sex all the time just good conversation.

  4. October 7, 2015 @ 10:22 pm Phoebe

    I don’t know where to begin. I lost my husband two years ago from kidney failure. Im living with 93 year old women. Who get up when I wear a skort outside. Grrrrr. Whatever. I don’t want to live rest of my life alone.

  5. May 5, 2013 @ 9:06 am Elana

    I’ve had people tell me I have a barrier set up and men won’t respond to me because I am too distant. I don’t mean to be. How can I change that?

  6. April 20, 2013 @ 8:56 pm Alabama Girl

    I actually had a guy I met online who represented himself as educated and classy (he was a lawyer) tell me a dirty joke the first time we talked on the phone. I wasn’t so much offended as amazed because the conversation had been great up to them. I wondered if he was testing me, so I told him I didn’t like that kind of humor so he hung up on me! I told my friends about it and we all laughed, but I was pretty shaken up by the experience.

  7. April 13, 2013 @ 3:14 pm Sienna

    Passion Flower — I absolutely agree with you – flirting is visual as well as verbal, but here we are in the 21st century with most people in our age group looking for love online. For that reason we need new rules, I’m afraid.

  8. April 12, 2013 @ 6:13 am Passion Flower

    I am worried about social media and the effect it has on relationship building. I am 63, and I don’t think it’s because I’m an old biddy that I say this, Flirting is by definition visual as well as verbal, and one without the other is not the real thing. Flirting in the classic sense, which was a delicate and beautiful art, is a lost art.

  9. January 12, 2012 @ 10:20 am Walt

    I have met some nice women, but most of them want to know your financial status right away. I am sick of going to a restaurant, spending 50 or 60 dollars and having the woman expect me to pull out my wallet. At least we should split the tab while we’re still in an early stage of knowing each other. This has caused me more than once to stop seeing a woman.

  10. September 18, 2011 @ 2:42 pm Lillian

    Men sometimes use dirty words to test you, especially when a woman is over 60. They are afraid at our age we are prudish. I find that so strange, especially since some of the men our age are practically impotent. You wonder what they would do if you actually responded to the dirty talk.

  11. May 2, 2011 @ 3:52 pm Madame X

    A woman over 50 who is trying to be sexy is really kind of pathetic. This is good advice because it emphasizes being subtle and not trying to act like a 30-year-old.

  12. April 3, 2011 @ 11:05 am TooShy2

    It’s really hard to do this on the phone because you can’t see what the other person’s reaction is. My strength is being a good listener and that makes for dead silence on my end sometimes, so I lose them.

  13. March 19, 2011 @ 8:53 am Lauren

    I agree with Patsy. It’s hard to flirt on the phone because it can turn into phone sex pretty quickly.

  14. March 17, 2011 @ 12:49 pm Tilly

    This is good advice.

  15. March 17, 2011 @ 11:51 am Patsy R.

    I think a lot of men think telling dirty jokes is a way of determining whether you are a prude or not, and if you don’t laugh they think maybe you’ll be cold sexually.

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