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How To Kill Your OnLine Dating Chances


Your photo might be that of an attractive older woman gazing at the camera with intelligence and warmth. Your carefully crafted profile reveals your charm, wit, and optimism. You’re ready to complete the dating site’s registration form, and you’re about to make a fatal mistake that will cut your chances of attracting senior men by 80%.

You’re being asked to make a choice between two options. Is your goal a.) marriage or b.) a casual relationship?

Why not be honest? Your fingers dance lightly over the keyboard. You type “marriage.”

I learn a lot from the senior men in my Dating Gallery, and they all agree on this:

They don’t even think about contacting someone who has flat out admitted she’s looking for a marriage partner. Here are their reasons:

  • I was 35 years with the love of my life and I can’t / won’t replace her.
  • I don’t even know you – why would I want to marry you?
  • I resent someone who sets conditions before we meet.
  • My divorce taught me that getting married is asking for trouble.
  • Marriage is off my radar. I just want companionship.


MILITARY MILO and FIGARO both say they’ve been asked outrageously intimate questions by women who think first dates are for screening marriage candidates. These women ask about stock portfolios, home ownership, financial commitments to children and grandchildren, alimony, even the use of Viagra. At the end of my first contact with MILO he said he enjoyed our conversation because “it didn’t feel like an interview.”

I don’t blame those of you who continue to check “marriage.”  Like you, I remember being proud to be half of a couple, proud that someone had chosen me to be his “official” partner.  To us marriage is the norm.  But the fact that we’re dating now means we’ve passed though that experience and it’s time to give our perspective a tune-up.


Whatever your motives for checking the marriage option, give it a rest. Your senior man only wants someone to hang out with — at least that’s what he thinks. When he encounters no let’s-get-hitched pressure from you, he might just get down on his good knee and pop the question (pop the marriage question, not the knee) all by himself.

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'How To Kill Your OnLine Dating Chances' have 14 comments

  1. October 24, 2013 @ 9:42 am Sienna

    I love your story — the Restless Boomers are a great team. I hope my followers will follow you too. See you on Twitter!

  2. September 2, 2013 @ 3:36 am Cate R.

    Good information. We’ll toss in our experience.

    We met online and had a great experience. We were both up front that we’d had a long term marriage, understood the yard stick is getting shorter by the day, wanted friendship and intimacy, and clearly interested in something long term if that worked out.

    That said, we communicated only via email (no phone, no skype, no in person) for months before we met. It was a great opportunity to get to know each other and, equally important, ourselves and what we really wanted.

    Once we finally met, we haven’t been apart for more than a couple of days (and that was an emergency). That was almost twelve years ago.

    It takes all kinds and people need to just make sure they’re honest with themselves and the other person.

    Bottom line, as when we were younger, you may have to kiss (or e-kiss, the beauty of online dating) a lot of frogs until you find your mate-charming!

  3. November 5, 2011 @ 2:37 pm Willy's Willy

    I think Mr. Shadenfreudian Slip is just looking for a chance to show how clever he is and what a great vocab he has. Ululate. Smooooooth, Dude.

  4. October 20, 2011 @ 1:48 pm Sienna

    Mr. SchadenfreudianSlip: As a fair reading of my blogposts and my readers’ subsequent comments will demonstrate, both I and my readers LOVE men, embrace whole-heartedly their quirks and foibles. If they hadn’t quirks and foibles — none to match our own — the game of love would be no fun at all. Thanks for your comment, though.

  5. October 20, 2011 @ 6:44 am SchadenfreudianSlip

    C’mon. You come off sounding high and mighty, echoing the same pabulum that women of ANY age range ululate. I’m referring specifically to your home page replete with smug comments.

    If women find men as freak-showish as y’all seem to, then why don’t you just find a woman to live with instead if you yearn for companionship? As often is the case, women would rather complain about something instead of ever doing something to achieve some modicum of satisfaction with her life.

    This character trait–especially of English-speaking women–is a natural result of the aftermath of the 60’s and 70’s redefinition of all things female. If you have one empathetic bone in your body, one molecule of objectivity, you’ve surely got to admit that women found a way to get it all wrong, and at the same time convince society at large that men are evil and must be stopped.

    Yeah, and I’m a free-thinking weird kinda guy, but so the F what? To me there’s no display of unbridled prejudice and hate than being the only male in the vicinity of a pack of complaining “you go grrrl” types.

  6. September 10, 2011 @ 8:45 am Sienna

    Patsy — I think there are very few men who wouldn’t welcome a chance to get to know someone in advance of any marriage plan. Men in our age group are still creatures of a culture in which the man was supposed to pop the question.

  7. July 20, 2011 @ 3:24 pm Cate

    Oh please ! I had a dinner date with a guy and thought I was interviewing for a domestic with benefits. He asked if I was a good housekeeper and a good cook. He then asked if I liked sex.
    I had a great meal, said good night and left. What a Bozo.

  8. June 25, 2011 @ 10:41 am Sienna

    Tilly, you are echoing the choice of many senior women who lovingly nursed husbands through long illnesses and simply feel unable and unwilling to make the same sacrifice for someone with whom they did not share a long history of companionship in good times. The same goes for the sacrifice of doing everything “his way” just in order to keep things on an even keel.

  9. June 19, 2011 @ 6:13 am Tilly

    One reason for women not checking “marriage” is that you might get a man who is looking for a caretaker. I was with someone for a while and contemplated marriage but when I realized I was trading independence for doing things his way for the rest of my life I decided against it. He wasn’t able to deal with my wanting independence and we broke up. I miss him, but I’m glad I didn’t marry him.

  10. May 20, 2011 @ 7:46 am Sienna

    Apparently some of the best dating sites do offer the choice you’re suggesting, Joan. Thanks for your comment – and for reminding us of your latest book — the unique, authorative, and wonderful Naked At Our Age, which I hightly recommend to my readers.

  11. May 19, 2011 @ 11:02 am Joan Price

    Interesting conversation here! Instead of checking a box, wouldn’t it be nice to be able to write in what you really want to say you’re looking for? e.g. “Friends first, then we’ll see where it goes” or “Let’s just get to know each other for now” or “Let’s just date without an agenda”?

    Joan Price
    Author of Naked at Our Age: Talking Out Loud about Senior Sex ( and Better Than I Ever Expected: Straight Talk about Sex After Sixty (
    Join us — we’re talking about ageless sexuality at,

  12. May 18, 2011 @ 2:34 pm Carrie

    I see your point here, but you should know that “casual” sometimes sends a message that you are a loose woman interested in sex.

  13. May 17, 2011 @ 6:36 am Patsy R.

    what about the guys who are looking for a marriage partner? they’re likely to pass you by if you say “casual.”

  14. May 12, 2011 @ 3:10 pm Penelope

    No matter what situation, no man wants to talk about the future before getting to know someone. I think it’s unfair to expect too much information from him but a little is appropriate.

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