Flirting training wheels

Midlife daters have admitted to me that they don’t know how to flirt anymore. Some even say they never knew how. Now that they are single in midlife, they are feeling they need — and want — to learn.

But how does one practice? Chatting up strangers in the grocery store? Smiling and winking at others in the gym? Offering, “You look familiar” to someone at the coffee shop?

Instead of strangers, should one practice on folks you think are single at church, school events or work? What if they aren’t single and they think you’re being inappropriate? If your flirting backfires, you’re stuck seeing them at future functions.

So what’s a neophyte flirter to do?

For those not quite ready for my Flirt-O-Grams, you can join It’s a free site that lets you enter minimal information about yourself and start flirting with people all over the world. Or you can limit the focus of your flirting to an age range and/or geographical area.

While I see minimal value for those who feel comfortable getting their flirt on, for those needing some remedial practice it’s a safe place to start. Think of it as flirting training wheels.

I asked my pal who’s doing publicity for the site why someone would join since one can easily flirt on any dating site. He said the beauty of this site is members don’t really have to intend on meeting or talking on the phone. It’s for folks who like to have some flirty banter with no strings attached. While I don’t see myself ever being drawn to this concept, he says it’s very popular in the UK where it began. Especially with those who don’t feel comfortable flirting in real life — yet.

I agreed to try it out so I could tell you my impressions.

First, because membership is free, the level of class, intelligence and education skews low. Some of the introductory messages showing on guys’ profiles are crass. Just move on.

I got flirts from 18 year olds on up. None had anything enticing on their profiles that made me want to respond. When I searched by 40+ men near me, there was no one with whom I wanted to flirt. If I didn’t care their age or location and just wanted to play a bit, I could probably find someone flirt worthy.

Assuming you do find folks to flirt with, you can get their messages via text. I don’t really want to be interrupted with texts by people I don’t know so I didn’t enable that feature.

Know that you have to buy Flirt Points to get improved functionality. For example, if you want to search by those near you, you have to buy 75 points for 24 hours of this feature. For $1.99 you get 250 points.

So, the bottom line is: if you want to just practice your flirting skills, sign up for the site. If you are already comfortable flirting in real time, pass.

Want to understand the ins and outs of cyber dating? Get your copy of Winning at the Online Dating Game: Stack the Deck in Your Favor.


9 responses to “Flirting training wheels”

  1. Mark Avatar

    This is flirting in chat, right? Does that even count? disregard chat and email and even phone calls. I’ve done this with more than a few women and then the face-to-face was a complete zero.

  2. Cathy J Avatar

    Mark – sorry to hear that.

    I like the practice idea for that market with the website.

    Still all comes down to expectations though. If you go into it feeling great, beautifiul, sexy… and have fun – everyone will want to flirt.

    Recently I heard or read someone say if the one you are talking to someone who doesn’t hold any interest, even think mentally “Next!” Now realistically this could be what men have been thinking and doing for years. Try it. Don’t take rejection personally (they don’t even know you!)

    Flirting involves making eye contact, blowing hot and cold ie interested but not too interested… there is an art and to watch an expert is like poetry in motion.

    Some movies on this topic can also be fun for good and bad examples. ‘Hitch’ is always good for a laugh!

  3. Anna Avatar

    Flirting has always come easy to me. I like men a lot and its easy to smile, be chatty and witty. Then again, I can find myself “flirting by mistake” with men I am not even particularly attracted to and that can send wrong messages. My sisters tell me I am just a natural but in the work place I really have to watch myself 🙂 I think its just something I am born with and I don’t even know I am doing it at times. It has even inadvertently gotten me into trouble with wives of men so as I get older, I keep myself in check and try to tone flirting down a bit. I think the trick is to like everyone at first sight and only dislike them if they behave or do something that is crass or not particularly likable.

  4. Adrienne Ragland Avatar

    Great piece of information. Will share this with my readers (single women 35-55). I guess because I’ve never been married/had children I’ve never been off my game. Although I’m not an ‘online dater’ myself, my readers are. Will be sure to promote this site to them. – Adrienne Ragland, Editor/SP

  5. Karen Avatar

    This would creep me out.

    Because “bad” flirting is often the same as awkward, overly-sexual, come-ons. I get enough of that on the regular online dating sites! And why would I encourage random men to “practice” on me? ugh!

    I personally don’t feel that “flirting” skills are all that important when dating. I don’t like the “smooth” men who try to flatter me etc, anyway, and I know that many men are also turned off by women who lean in and call them “darlin’” and bat their eyes and all that.

    You don’t need “a line”. All you need to do is be a “regular person” and demonstrate that you have some social skills!

    Think about putting the other person at ease, and draw them out by asking questions about themselves. Treat the person you are with as the most important thing in your life right then–turn off your cell phone and pay attention. Smile at them, and let yourself show a little twinkle of your great personality. Come prepared to the date with a few intererting things to talk about that you can bring up if there’s a lag in the chatter. Be cautious about bringing up the 3rd rails of conversation–politics and religion. Don’t brag, don’t make sweeping generalizations about anyone (especially not your ex), and don’t, don’t, don’t ever leer or make sexual remarks. Don’t cuss. Be polite. Be polite to the waitstaff, too. Act and dress appropriately depending on where you are–whether your in a formal restaurant or baseball game.

    I’ve gone out with guys who couldn’t even do this! One man asked me to marry him on our first date (yikes!). Another man showed up at a fancy restaurant wearing motorcycle leathers–and not nice ones either, really sweat-soaked leathers that smelled. Another guy spent most of the date ranting about how much money his ex wife was spending, the rat! Another guy talked non-stop about himself and never asked one questions about me, not the entire night–it was an extreme bore-fest. Another guy interrupted me when I was talking and kept checking and sending messages on his Blackberry. One man saw fit to mention on our date how he’d hit his ex-wife in the face (Only once, but she deserved it!) Another guy on a first date said the dating service always sent him dogs, but that he thought I was really good looking! When I ignored this random comment and kept talking about something else he interrupted to say, “hey didn’t you hear me? I said that you were really hot! That’s a compliment!” To which I answered ” oh, uh,,……..” Then there’s the man who twirled in front of me when we first met, on our first date through a dating service, saying “don’t you like these acid-washed jeans? They are sooo hip!” (I’m not sure if he was just a fashion victim or gay.) And there’s the man who (again, on our first date!) started sobbing and saying how he still loved his ex-wife….! And one guy’s idea of a conversation starter was, “how tall are you and how much do you weigh?”—and this was at a face-to-face meeting, not online where I suppose there might be some reason to ask this!

  6. Mike Lowrey Avatar

    Damn Karen, I’d swear off dating if I had that bad history.
    If you found these guys through a dating service, I say find out where their HQ’s are and throw a damn Molotov Cocktail in the front door.

  7. Karen Avatar

    Yeah, Mike, I stopped using any of the 2 lame (but pricy!) dating services I had been using after 1 year. You had to sign up for a year at a time, so trying the services was a gamble that I decided to take for a year.

    I live in a smaller city and I’d had a hard time finding anyone remotely “dateable” in my age group (ie similar education, professional job, not a convict etc.). But it was clear that the “dating service” was just sending me out with any breathing xy chromosome on their lists, and not doing any of the “careful matching” and etc that their ads said they did. Possibly these services (they’re national franchises) would work better in larger metro areas with more people to choose from, but they don’t work in a small town.

    Oh well, at least I got a lot of funny stories! & it was a boost to my confidence (kind of?) to see how many guys out there were worse off that I was, trying to date after divorce while suddenly realizing (ugh) that we were in middle-aged bodies.

    I decided to write the year off in terms of expecting romance and focus instead on the educational and humor value available from the experience. And I thought many a time, “I may be shy and old and kind of un-hip, but at least I have enough rudimentary social skills to know I shouldn’t do that!”

    It made me think, too, about my 2 ex-husbands (who were both total losers–everyone told me so before I married them but did I listen?) and how I should have spotted their dysfunctions right away. I like to think I’m unconventional too, so I tended to overlook people who didn’t adhere to social conventions–but now I think that’s a huge mistake. ie Someone who won’t or can’t realize what minimally-appropriate behavior is, even on a first date where they’re trying to make the best impression, is not someone that I want to get involved with.

  8. RWH Avatar

    Flirting is a thing the human body is made with. I rather call it an instinct rather than an act. As for me, flirting is a thing I can do naturally when it is needed.

  9. Joe Avatar

    @RWH: Easy to say the human body is made with it and it’s all you need, when you can do it naturally. By the same logic, the artist can say that creativity is something everyone is born with, and the scientist can say genius is something everyone is born with. Yet not all of us are creative geniuses making beautiful paintings while figuring out cold fusion.
    Whether it’s an inborn quality is irrelevant anyway, really. What matters is the bottom line: are you good at it? If yes, good for you. The rest of us, we need to up our game if we want to become good.
    Of course, Karen’s POV (that flirting isn’t needed) is valid enough for some (again, not all), but for those that want to get better, training wheels are welcome.