Dating After 50, 60, 75 — Making Our Own Rules

Image for This New App Is Like Tinder, But For HotelsOnline Dating Over 50: The Rules of The Game” on Huffington Post began,

Monica Porter, who dated “dangerously” for a year, shares nine top tips to help protect yourself, including: don’t believe anything, be careful who you get into bed with and split the check. If you’re looking for romance through online dating, make skepticism your starting point, says Monica. 

Sure, “be careful whom you get in bed with” and “split the check” are reasonable, whatever your age and whether you’re dating online or some other way. But the negative attitude overall made me cringe For example,

Rule #1 of dating over 50: Don’t believe anyone. Emotionally, you need to construct a wall around yourself which nobody can penetrate until you believe it to be safe. People will plunder your emotions without compunction if you let them. It is up to you keep them locked up, like jewels.

Really? I’ve been online dating for a while now, and though I have my own frustrations with it (see my advice to men here), fearing that my precious emotions will be plundered if I don’t lock them up is not one of them.

Personally, I think that most people of our age who are using online dating sites are looking for love/ lust/ sex/ adventure/ friendship/ companionship, or some combination of these; feel as vulnerable as we do; and have good intentions. Am I naive?

Isn’t the point of a first date  to know each other enough to decide whether we want a second date? Isn’t part of that being ourselves, talking openly, and, yes, risking a little? I’ve met people who have their emotions locked up, and I have no interest in dating them.

I invited the fans of my Naked at Our Age Facebook page to weigh in. Boy howdy, were you willing! Here are some of your points:

Janet, 55: I agree, it is very negative. If you go into online dating with fear and negativity, that is what you will attract. I suggest: Know yourself, be clear about what you expect from the site, be clear on the qualities of a date you are seeking, be ruthlessly honest because you have nothing to lose — you don’t want to waste time in a charade. This is the time of life to be real. Be you, be positive, have fun and you will attract what you put out.

Dana, 62: I tried online dating and it seemed like every man I met had a laundry list, and I was too short, not brunette, too chunky, not enough like their ex wife, too much like their ex wife, too independent, not independent enough, too sexual, too frigid, and on and on. They had this woman pictured in their mind and were looking for her and her alone. My strongest recommendation would be not to make snap judgments at the first meeting. Be willing to let things unfold, be curious. Resist the temptation to judge a book by its cover. Just relax and don’t be on the hunt for your “soul mate” (whatever the heck that is). Find a true friend, a joyful companion, a kind soul and be nice. Let life, God, the universe, fate (whatever you want to call it) choose for you.

Jim, 58: As negative as it may be, is the article accurate? I say, for the most part, yes. Photos are old, many of them are of flowers, their dog, whatever. Would it be nice for a woman to offer to help pay for a nice dinner? Never happens. Not that I would accept it either, but the offer would be nice. I think we all have preconceived notions of what we want, but I agree that you need to let things flow. I find that many women aren’t ready to date, let alone have a new relationship. After 3-4 dates, it’s “I just don’t think I’m ready,” or “my ex BF is really trying to be a better man so I’m going to go back and give it another try,” or “I thought I was ready but now I’m not sure.”

Ruth, 67: I think the Huff Post article is valid to some extent — don’t believe anybody! It doesn’t mention that you can ask for a reference after you’ve met someone for the first time and before you hop into bed with them. You can find out about the person’s honesty and relationship history from someone else’s point of view. I don’t agree with the statement, “If you meet someone you fancy, by all means enjoy good, fun sex. But – hard-nosed as it sounds, and I can’t pretend it’s always easy – take the emotion out of it or you will be hurt over and over again.” I can’t take the emotion out of sex and I’m not sure many people can.

Paula Ellen, 53: I find the photo with the article pretty offensive. Why isn’t there a photo of a 60-year-old, gray-haired woman with a thirty-something male? Jesus.

Brian, 64 :

I’m a verbal guy, I’m not interested in profiles without a lot of writing either in the profile essays, or in the explanations of the questions on OKCupid. That’s where I gauge such things as sense of humor, care for others, and intellectual curiosity. I wonder what women are thinking when they post a profile picture showing them scowling or otherwise looking unhappy. My correspondents tell me that they get tons of messages from men on the model of “Hi beautiful, what’s up?” (That sort is the more tasteful) I can’t give advice on how to handle this, except to put clearly in your profile something that you ask for a comment on, if only to see if someone actually read it. I sent a woman one of my usual cheerleading notes, telling her how much I loved her profile and wishing her good luck. Six months later, we’ve got a very fine romance going, despite the long distance. As it happened, one of my lovers had just said goodbye for reasons best known to her, and I had some time/energy to spare.

So, be careful what you don’t ask for. You may get it.

Ashton, 62: I agree that that article is way too negative. I’m a fan of OK Cupid and I think you need to go into it open-minded rather than paranoid. My #1 rule of online dating is to meet sooner rather than later.

Cyril, 65: While I agree that the wording is negative and excessively emphasizes the need for caution, we should not be gullible or leave ourselves open to exploitation, whether by a date or a rogue trader. Simply put, make sure they have earned your trust before you open up.

Chuck: I’m 74 and my honey is 78. We met on JDate two years ago. The obvious catalyst is honesty–and candor. We got the heavy lifting done on our first date (my alcoholism and depression, her husband’s dementia) and moved on from there. Respecting one another’s history and allowing space for individualism, these have worked so well for us.

What do you think? I welcome your comments. (Please include your age.)


  1. Josie on October 30, 2014 at 8:46 pm

    For the most part, I find online dating fun. But I've had my doozies too. An 18 year old (I'm 77) posted an email to me that simply said "Wanna bonk?" I must confess I laughed, then sent him the following reply "Would that be before or after I've changed your nappy?" Needless to say, he didn't reply, nor did I expect him to. I love hearing from men who show an interest in me (sexual, of course, but me as a woman).
    Men who are prepared to take the time to chat, get to know one another, and don't just cut to the chase. What I value highly in a man is kindness, gentleness and above all, a sense of humour. I love a man who can make me laugh!

    • Jeff Johannigman on October 30, 2014 at 8:55 pm

      Admittedly, a big part of the problem most women have with online dating stems from the small but very visible minority – the "horny boys who have no clue how to approach a woman". They tend to spam every woman they can find on dating sites with those "wanna bonk?" type messages. In the meanwhile, more cautious but caring guys often feel like they are getting lost in the spam you are receiving from the horny boys. I hope that's not the case!


  2. Jeff Johannigman on October 21, 2014 at 4:39 pm

    I am 53, and have been using online dating sites for about 4 years now. I have tried Plenty of Fish, eHarmony,, and a few others, but the one I keep coming back to for the best results is OkCupid. I have found its extensive essays and matching questions, along with its flexible matching algorithm, to be the most effective at finding women I am "compatible" with.

    Thanks to OkCupid I have found three long-term romantic relationships and numerous casual female friends. Maybe I have been fortunate, or maybe I am just good, or maybe just persistent. But my advice is simple – The most important word when it comes to online dating is not "caution." It is "patience."

    OkCupid can do a very good job of predicting compatibility (do we share similar interests, values, and tastes?) But nothing predicts chemistry. That only comes from meeting face-to-face.

    For every one of my long term romantic relationships, I probably met at least 20-30 other women from OkCupid for "coffee meets." They were just an hour to chat at a local coffee shop, get to know each other, and see if anything clicks. Was I disappointed or frustrated that 95% of these meetings did not generate any hot, romantic chemistry? Not in the least! They were almost all interesting women who could be nice friends (and several of them now are). We had pleasant, stimulating conversations, sometimes exchanged contact info, sometimes stayed in touch, but rarely did I actually date any unless I felt the "ping" of potential romantic spark.

    I am now madly in love with a woman who first contacted me six months ago on OkCupid. Our coffee meet set my romantic "ping" on overdrive, and it ended with a kiss that could flatten several small villages. (For the record, I almost never kiss at a coffee meet, but the chemistry with her was amazing.)

    In short, use the sites (OkCupid in my case) to find people you are reasonably "compatible" with. Don't waste too much time texting, chatting, or emailing before meeting face to face. (I have found that you can easily create inaccurate, overly idealized, versions of that person if you spend too much time corresponding before meeting.) Meet as many people as you have time to enjoy meeting. Do not expect chemistry in 95% of the meetings, but do expect to have a nice pleasant conversation. Be persistent, and eventually the chemistry will be there.

    Enjoy the quest as much as the treasure at the end!


    • Joan Price on October 21, 2014 at 4:46 pm

      Jeff, I hope that everyone who is grumbling about the number of non-ping dates reads your brilliant comment here! I gave similar advice at a dating workshop I gave last weekend, and it's great to read the same strong viewpoint from you. The way you described your first meeting with the woman you love made gave me a tingle!

    • Earl on November 28, 2014 at 9:19 am

      Wow Jeff, that is great advise. Using a date site to actually make appointments! Still meeting face to face is way better to build a relationship between the two. I think its wonderful that you explain that a dating site is not a magic tool to get laid. Nice post!

    • Jeff Johannigman on November 28, 2014 at 6:09 pm

      Seems pretty obvious, Earl, but I am still amazed at how many women think that they will instantly meet their "Prince Charming" with the first guy that they match with on a dating site. On the flip side, it disgusts me how many guys think it's an easy way to get lucky just by spamming enough women.

  3. Dr. Dorree Lynn on October 20, 2014 at 12:49 am

    Dating at our age has many pluses. Most are seeking their final love. Slow,authentic, candid and careful. Most seek love and have developed the wisdom to seek well.

  4. Dan on October 19, 2014 at 2:04 pm

    I dated successfully 5 years while in my mid 50s (pretty darn good marriage, 7+ yrs now with the best woman on the planet for me). My tips and 2 cents?

    + don't spend more than $1.50 on a 1st date; plan 90 min. learning something over coffee about yourself and what you want; ask her lots of open ended questions
    + do the numbers; I once had 3 coffee dates in one day; dating is work; most get what they pay for in invested sweat and time
    + don't do sexual things too soon; you'll get hooked and only have 1/2 what you needed to find
    + journal after each date; what worked/didn't
    + don't be afraid to ask and be clear about what you want and need; toward the end I always asked if she was OK with me touching her hand; it is amazing what you can discover with that small ceremony; and I always asked if she was orgasmic and enjoyed touching herself. Yes, on the 1st date. I had to know this.

  5. Joan Price on October 18, 2014 at 8:46 pm

    I've often thought that it would be smart and fun to have an "Exes Mixer" — you bring an ex for whom you can vouch as a decent person, even though he/she wasn't right for you. Everyone there has the seal of approval of the ex. (I hear the cynics now: "That would be a darn small party, Joan.")

    • Anonymous on October 22, 2014 at 3:07 am

      long before the internet there were a few guys i knew who fit this criteria – Good For Someone Else. I happily introduced them to my friends.

  6. David M. Pittle on October 18, 2014 at 5:42 pm

    I'd love to make a contribution to this discussion, but the previous commenters have said it well.

    I continue to make occasional first dates on OKC. Sometimes leading to second+ dates. The very least I usually get is a pleasant conversation (and a good cup o coffee) but the worst was a woman who made her disdain for men who are both overweight and have a less than $100,000 income, clear and verbal and then walked out.

    But that was about her, not me. She did not "plunder" my emotions or leave me in pain. People do what they do; it is rarely about you, almost always about them. In fact they do you a good service by exposing themselves this way.

    • Joan Price on October 18, 2014 at 8:43 pm

      "People do what they do; it is rarely about you, almost always about them. In fact they do you a good service by exposing themselves this way." Well said, David!

  7. Mindy Mitchell on October 18, 2014 at 3:13 pm

    Thank you, Joan, for clarifying what I believe to be true about online dating. Being careful is assumed. Being responsible for what I put out there is my responsibility. Having clarity around my wants/needs keeps it simple. I believe in playing fair and that has served me well. Mindy, 62.

Leave a Comment