5 Online Dating Message Mistakes to Avoid

Sexy Woman on Laptop

I had taken a little break from online dating, as I was having trouble juggling my many relationships. Then a few went kaput and I felt the itch to put my dating profile back up. I haven’t had much time to look around, but I have received a lot of messages. And the not-so-good ones gave me inspiration to write this post. It seems that there are some common messaging mistakes that men make. I almost feel bad for them because most women won’t even check out the guy’s profile after reading these

5 Message Mistakes to Avoid

1. Too Sexual
This depends on the type of dating site, of course. But most women (unless they state they are looking for casual sex only), don’t want the wham-bam-thankyou-mam of messages. It’s a turn off and reeks of insecurity. And we’re not into the bare chest in the mirror selfies either.

2. Bad Spelling
This includes grammar and punctuation. Not everyone is an English nerd, but even if it’s not your thing, get a friend to proofread your profile. If a woman agrees to go on a date and finds out later how terrible your spelling is, she’ll have plenty of other good things to focus on and will let it go. No one will respond to a first message that sounds Neanderthal.

3. Too Many Messages
Do not send multiple messages… to the same woman. It looks desperate and is annoying. A single well-crafted message will always have a girl checking out your profile. And if it’s well-written and she senses compatibility and an attraction, you will get a response. You may think multiple messages tell her that you really really like her, but she’ll worry that you’re needy.

4. Too Short
“Hi, how’s it going?” or “How was your day?” are way too short and vague. These messages are too easy and seen as extremely lazy. I don’t check these profiles out, ever! If a man can’t spend the time to carefully read my profile and write a message that is specific to who I am… bye bye. A little effort goes a long way, gentlemen.

5. Age-Related
Most internet dating sites ask you to list your age in the profile, and I think that’s important in narrowing down your focus. But… there are no-no’s when it comes to this. Because I look young for my age, I often get messages that comment on this, and although meant to be flattering it also makes me feel objectified. I even had a recent message, where the man asked when my profile pictures had been taken (last year thank you very much!) as if I had used ten-year-old photos.

I may have to write a part two to this article if I receive any more bad messages. I’d love to hear from both men and women about message pet peeves. These stories can only help!

Best Poly Dating Sites: The Polyamory Today Guide

Tell us what you think! 5 Comments

  1. oldergent371

    February 27, 2014 at 9:23 pm

    Hi again, Holly.

    There is so much tokenistic BS said about sex & older folks.

    Since retirement from professional life in early 2005 my wife’s libido has taken off. She still juices like a young woman. She has a lovely body that can still turn me on since I first saw it naked in 1959. We men & our propensity for the visual delights! I have long considered the female body to be the highest form of art. I’m fortunate to have an in-house model to create photographic images that celebrate the female body.

    Retirement provides the essential element of TIME: to explore, enjoy & express one’s sexuality.

    Most mornings find us enjoying sex 8-9 am, sometimes also late afternoon. It’s a rare episode when My Lady doesn’t hit double figures.

    I use Viagra to keep up with her needs, biting off about 1/6 of a 100mg tablet. I jokingly call it my ‘drug of choice’, ‘rocket fuel’.

    My only regret is the much reduced volume of semen that I produce. That’s happened over the last say 10 years, from age 60. Until then I’d been a 5-6 shot man. My Lady used to keep a pair of cotton soakers in her office in case of little ‘accidents’. She also kept tissues in the car, once having to stuff some down her panties at a red light to stem a leak. Those days have long gone. I can still give her, however, a favourite sensation by cumming directly onto her clit.

    We still enjoy the fun that sex can involve. 3-4 times a year she has lunch with a group of woman friends. We play out a ritual on her return home. She rings the doorbell, I answer it. She hands me her panties & ascends the staircase, showing off her bum. She lies on the big bed, still clothed, & opens her legs. I never last long in those circumstances! A bit of fun, Holly!

    We both held senior management positions for 20 years. Both jobs involved high levels of stress at times, not conducive to good sex.

    Our time in retirement is our own. I write (I have two books in literotica genre in print), My Lady paints in her studio. We find that this aesthetic sharing reinforces our sexual stimulation.

    The couple we share with occasionally are lovely, about our age. She is a late starter to the world of really satisfying sex & sometimes causes mirth at the voracity of her appetite.

    We are both fortunate to be in good health, another key element in good sex.

    Best wishes.

    John Australia

  2. John

    February 23, 2014 at 3:27 pm

    I agree with the points you make, Holly.

    We will NOT respond to cock shots. Nice shot say from waist up, nice shirt, lovely smile – there’s a start! No thinking woman is going to fall about, drooling over a cock shot. We make the assumption that a man has a cock.

    A man must sound interesting to us. A range of interests that are compatible with ours. An interest in the arts (my wife paints, I write); widely travelled (we’ve made 18 trips abroad which have broadened our experience comprehensively); courteous, articulate, well mannered & well presented; well educated; & carrying no personal baggage (we will NOT entertain the idea of a cheating husband or partner).

    How one goes about making oneself sound interesting is the exercise. Many will not find our criteria helpful & my point is simply to make the effort to present oneself in the most attractive way possible.

    We take our time. That paid off for our first sharing episode which was brilliantly successful. Our friend proved as interesting as he had sounded. I met him initially, then we had a marvellous picnic so my wife & he could get to know each other. Only then did we book a day rate room at a 5-star.

    I like your reference to “Neanderthal” replies. We’ve had a few. Tedious. How anyone would respond to such is beyond my ken.

    We now have the advantage of a most satisfactory sharing arrangement with another couple that precludes our need to rely on a site. If someone really, really interesting happened along, however, we would consider establishing initial rapport.

    We enjoy a wonderful sex life of our own, making love pretty much every day. We share from a sense of adventure, not because of deprivation. Which leads to my final point: not everyone who posts on a web site is starved of sex. Some are simply seeking to extend & enrich their sex lives.

    • Holly


      February 27, 2014 at 7:40 pm

      Hi John. Thank you for this lovely comment. I love hearing from singles and couples who have found harmony in their love lives. For some it takes a long time, so it’s great to hear about your journey to a satisfying arrangement, as well as your dating tips!

  3. John

    February 21, 2014 at 9:48 pm

    Happy to share our impressions with you, Holly, per email. Much to tell.

    J & C

    • Holly


      February 23, 2014 at 2:23 pm

      Hi John. We don’t communicate with our readers through personal emails, but we’d love to hear your thoughts in the comments section of individual posts.

Tell us what you think! is your source for everything related to polyamory dating sites and poly relationships. We post tips and advice for polyamorous lovers and those seeking threesomes and group adventures. Enter the world of polyamory with exclusive articles, polls, site reviews, reader stories and more. If you would like to receive our bi-monthly newsletter, please sign up using the subscriber form above.

Copyright © 2019

To Top