Online Dating at 75: Granny Gail Tells All


Here’s one from the archives for everyone going back in the dating pool.


In her memoir “Granny Is My Wingman,” Kayli Stollak, a single girl in New York City, enlists her 75-year-old granny in North Palm Beach, FL, to help her out of her post break-up funk. Granny suggests online dating; Kayli convinces Granny to try it with her. Through the course of several chapters they cheer each other on as they share their good dates, bad dates and outrageously ridiculous dates.

Granny is a trash-talking yenta with an anecdote or piece of unsolicited advice for every situation. While 20-something beauty Kayli has trouble finding husband material, Granny Gail has trouble finding men who can still drive at night. As the two women grow closer over tales of their dating exploits, they learn that the hunt for happiness is the same whether you’re 25 or 75 – although the hunt for sex is a lot easier at 25.  

Most of the publicity for this book has focused on Kayli, with Granny simply being there as an adjunct, but we wanted to find out more about Gail’s experience. What was it like for her to put herself out there at 75? Is there hope for women in their 70s to find love, or at least find a date?

We talked to Gail by phone at her home in Florida.


What’s the difference between men who are dating in their 70s and women when it comes to what they’re looking for?

To be quite honest it’s very similar. Men always look first for appearance, women are more interested in things in common, and both want someone they can talk to – unless they’re looking for one night stands, but not too many men in their 70s and 80s are looking for a one-night stand. That’s one advantage of senior dating.

What annoys you the most about the men you meet?

It’s very difficult to shut them up if you want to be polite. Sometimes I’ll just tell them it’s getting late. What’s worse is when they just want to talk on the phone. I’m not interested in a telephone affair, and that’s what a lot of these schmucks are after. There’s so much hoopla when we schlep these conversations along, that by the time the actual date comes around it’s like, eh, I’m tired, I wanna sit on my couch and watch Desperate Housewives.

How has the game changed since you were last playing the field?  

The game is different at 25 and 75. Ten to fifteen minutes in the world of 25-year-olds is an hour of conversation. Ten to fifteen minutes with an old fart of 80 or older goes on forever.

What about sex?    What would it take for you to get naked with a man?

I tell you one thing, I would not take my clothes off and prance around in high heels and sunglasses. Would I go to bed on second date? No way. At this age you have to know each other well enough to communicate. He might confide that he needs Viagra, or that he can’t get it up; you might have some issues.  I want to get to know someone on a cerebral level.  If they’re only thinking about jumping into bed because they’ve taken me out to dinner, forget it. I don’t look forward to dealing with an old, messy, farty situation. I’ve had very nice relationships in the bedroom in my life. I’m not about to ruin that with a wobbly sack of bones.

What kinds of lies did you find that men told in their profiles that you discovered when you met them?

That they’re 5-foot-eight when they’re five-four; that they’ve traveled the world when they’ve been to Hoboken. They want to make themselves more worldly, more interesting, more than they were in younger life. They regret not having done more. And a lot of men are interested in  a nurse and a purse, but they don’t exactly admit that.

What are your deal breakers?

If they can’t drive at night they have to live close by because I’m not driving far.

They have to be able to walk.  A nice man who was older than me, we met at restaurant, and when he could barely get up to greet me I said to myself, this is not what I’m interested in. I had to help him into his car and call him to make sure he got home safely.  He was a nice man and I’m sure that two weeks later he found some woman to live with him.

I don’t like someone who’s cheap. He  should pick up the check.  One man invited me out and said to me, either we go dutch or you pick up that tab. Kayli said, “Granny that’s not going to happen, he’s playing with you.” But he was serious.

What was your worst date?

My worst experience was getting stood up. We were meeting about a mile or two from where I lived. I walked in and saw a messy guy sitting at a table, walked over and asked if it was him, and he said yes. We walked out together and he said, “I have to go now,” and he left. That was a first. I got to my car and called Kayli. A rejection can seem harsher when you’re older.

Did you find that  the older guys are going for younger women?    

If they were looking for younger women they weren’t out with me. I think older men want women they can talk to and have things in common with. Commonality doesn’t happen when you’re 30 years apart. Would a 75 year old man be thrilled to have dinner with Kayli? Yes,  but he’d fall asleep anyway.

In the book you got to pick and choose between suitors, which might make you the envy of many women your age. What was they key to your success?

I wasn’t ever looking to marry or live with anyone, but I still enjoyed our time out. I put on my makeup and a nice outfit and had conversations. The lack of expectation is appealing to men. But you don’t want to go out feeling you’re going to have a terrible night. I had a positive lack of expectations.

What’s more important to older men,  looks or personality? Does the search for big boobs ever end?

Big boobs are way less important as you grow older.   

Do you have any tips for women your age who want to start Internet dating?

Do your online dating with a friend, grandchild, daughter or son. Find someone single who will go through it with you. Compare notes with a friend. Work on your profile with someone. Kayli read me her profile and I made corrections, and vice versa.

Meet at a restaurant and leave from there, I never had anyone pick me up at my home.

It’s all in your expectations: If an old man asks you out, go out, look him over, see if you can make a friend.  Young people want a commitment. I just want a fun, interesting  pleasant evening. If it goes further fine, if not, fine.

Sometimes you get nervous, but if you keep expectations low it may build into something beautiful.  At 75, a male friend can be very nice to have.  I like to listen to men talk and enjoy the difference between the way I think and they think.

Did you find anyone special?  How about love?

I didn’t fall in love, but I did find steady male friends.


“Granny Is My Wingman” (New Harvest) is available in hardcover, Kindle, audiobook and MP3 versions. Click here to find it on Amazon.


7 responses to “Online Dating at 75: Granny Gail Tells All

  1. I find being single at 75 is not where I thought I would be. I always wanted a life-long relationship with a loving, caring, partnership-oriented man. Alas, that was not meant to be. Widowed at 27 placed a heavy black mark on my psyche that has remained. I have learned to live with the loss of “young” love. Now I would like to find my “last” love: a love that has depth of meaning, loyalty and commitment. So I ask myself……………what do I have to offer? I offer an open heart.

  2. This may not be the forum, but here goes. I am seventy years old, look sixty. I am tall, distractingly handsome (I am told), athletic, highly educated and gifted, youthful and playful, cultered, well travelled, articulate, progressive, open-minded, talented in numerous ways, a great lover in bed who loves giving pleasure—especially oral, loves women (especially fit older gals) and am a feminist. The problem? I scare the hell out of women my age and older. It is as though I am out of sync. I would love getting feedback from women about this. I will say this: many fit, smart, and attractive women seem to 1) not realize just how sexy and attractive they are at their age and 2) seem to be done with men. This all seems like such a waste to me. When I was a young man, I was callow and saw beauty only in youth and what we think of as youthful beauty. As I grew older and became a mature, I came to see beauty in age honed by wisdom and experience. As odd as it might seem, I see and feel beauty in the loose and wrinkled skin that age provides. This is difficult to put into words and one must navigate carefully here lest he be misunderstood. There is a spark, a light which can shine from within women even into their nineties—long after they have stopped perceiving themselves that way. This is not to say that all older women have this—but it does still still burn brightly in some. I must also point out that sex and love-making is always open to interpretation. Far too much importance is put on intercourse and penetration. Those are functions of reproduction (albeit, pleasureful), but are only part of the picture; intimacy is the key. To be natural in our naked skins, entwined, touching, licking, sucking, tasting—that is the stuff of man and woman together. Revisit the poems of Walt Whitman who sings of the body electric to know that these ideas are not new.

  3. Fear not. Help is on the way for I know the secret. For those not currently in a Hugging relationship, allow me to provide facts as to where love connections connect. The most popular meeting ground: ALl pharmacies.
    Overheard one man saying to a woman while gazing soulfully into her shopping cart: “Gas and Heartburn Pills? Gee Whiz, Me too!” Burping, they frolicked carts interlocks to checkout.
    Be cautious, though. There is danger lurking in these drug stores. I was almost run down in the parking lot when a throng of stalkers on walkers ran after a fellow with those little blue pills.
    I actually prefer Internet Dating compared to my other pastime which was singing “Love for Sale,” at malls, with rouged cheeks, wearing my Anna Lucasta off-the-wrinkled shoulder gown. Since I became, um, a Senior Lady, now guys want me to pay for parking.
    Surfing the web is cheaper. I have met many interesting but sometimes unsuitable characters online.
    My first responder was from “Schlemiels on Wheels*.” He arrived on skates. I had to grab on to the back of his jacket as we whizzed down the boulevard for the early bird special.

    My next computer catch was a Dermatologist. He wrote that famous book, “7 Solutions for Highly Itchy People.” Last Valentine’s Day he bought me one long stem bottle of Calamine Lotion. I scratched him off my list.
    One nutty lover wanted me to call him Ida Lupino during coitus.
    A blind date drank his wine from a “sippy cup”. It was Rose’. I mean really! I can’t tolerate a man who can’t pick a side.
    I mentioned in an ad that I liked tall men. One came to the door on stilts. I really liked him. I had to end the relationship because I kept getting splinters in my thighs.
    Happily, destiny intervened during my last connection, though, and in a most unusual manner.
    Urging all seniors to practice safe sex, I myself usually wear a seat belt. But this one time, I did not. At the height of passion I whispered to my partner, “Are you comfortable?” He answered in a suddenly strange accent, “I make a living.”
    I laughed so hard…
    I fell off the bed…
    Injured my back…so now… as everything always works out as it should,
    I am currently dating my Chiropractor who truly is a nice guy but such a manipulator!

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