Dating When You’re a Senior

Seniors still hope for love after the experience of never having had it or of losing it  ▬ 

Sources

→ Boswell, James. The Life of Samuel Johnson, edited David Womersley. London: Penguin Random House, 2008. ||

→ Jones, Wayne. My Sam Johnson: A Biography for General Readers. William & Park, 2023. || ▬ 

Transcript

Hi, I’m Wayne Jones. Welcome to Newfoundland Boy, a podcast about me and the Canadian province of Newfoundland. This is episode 28: “Dating When You’re a Senior.”

18th-century English writer Samuel Johnson wrote that getting married again after you’ve been through it once is “the triumph of hope over experience.” If you read that one way, it’s bitter and cynical: why would you choose to go through that hell again? If you read it another way, though, it’s a simple calm statement of fact: marriage, like almost any human activity, has both good and bad, and if you choose to try it a second time, then you are relying on hope for a better outcome this time. (In passing, I published a bio of Sam Johnson last year: see the show notes for a link.)

I turned 65 two days ago and so am pretty officially a senior now. As a contrast, in the course last week of helping my mother clear out her townhouse to prepare to move to a long-term care home, I retrieved the identifying band that was put around my baby wrist a little while after I was born at 5:38 a.m. The other thing I did was subscribe, yet again, to Plenty of Fish, which seems to be the most popular dating site in Newfoundland. I say “once again” because I’ve been on it and off it like it’s a keto diet and I’m craving carbs. That’s the joke version. The truth is that dating in your 50s and 60s is one of the most frustrating experiences I’ve ever endured, and so what generally has happened is that I sign on for three months and at or before the end of that, I completely delete my account over the numerous problems associated with the site and with the people on it whom I’m trying to date.

Let me be clear from the start: I consider myself a decent person but I do not consider myself such a catch that I get baffled why scores of women aren’t trying to snap me up. I’m a senior. I’m what Generation Alpha, Generation Z, Millennials, and even Generation X call old (the first-year-of-birth range for all these combined is between 2013 and 1965).

On the Plenty of Fish site, affectionately or otherwise referred to by aficionados as PoF, I am looking for a connection with one of my peers mostly, that is a woman between her early 50s and mid-60s. Sometimes, when the fish aren’t biting, I cast my rod (no pun intended) into the late 40s. No matter the age, here is what I have discovered, after maybe thirty or forty dates or more, and even a couple of brief relationships. Note that I use woman or women here, but not as an indictment of that gender, but only because I am straight and date only women. I’m sure that people who date men find the same issues.

1.     Many women have had such horrible past relationships, and not sought counselling or therapy to address the trauma, that they are simply not ready to be in a relationship with a man. I communicated with one beautiful and very kind (but nervous and tightly wound) woman who had been physically and emotionally abused. She was in effect in trauma and made either conscious or unconscious efforts to sabotage our efforts at a relationship. Cancelled dates summarily. Told me only hours before that she just didn’t feel like a date we’d planned for a week. And during the one real date that I had with her, when she arrived at the restaurant and I commented sincerely on how nice she looked, she interpreted that as a compliment meant only to get her into bed. She was hard-working and intense, but had this sense of non-self-love inside her that compelled her to overcompensate by trying to prove to me, unnecessarily, that she was more than her work, that she was a smart person. We communicated a bit after that but ultimately I had to stop partly out of practicality: I wanted to meet some woman, and I couldn’t spend my time on dates that didn’t materialize.

2.     Many other women come with, as the cliché goes, baggage. Not just a stylish backpack, but a trolley full of luggage and a steamer trunk slung over their shoulders. They are often not over their previous relationship and either spend too much time talking about it and him, or assume—as did that first woman—that I was exactly the same kind of asshole they had already wasted too many years on. Just as some people have trouble completely ridding themselves of possessions they don’t need, they also have trouble just putting the past behind them and moving on to what many of them often refer to as “a new chapter.” Alas, many of those new chapters come with disclaimers and long prefaces and introductions.

3.     Some women are very leisurely about the whole process. Just during my recent sign-up at PoF, I chatted with a woman who was not only unwilling to endure a little wind and rain to meet, but also was adamant about, as it is often phrased, “friendship first.” This is code language for “no sex until we get to know each other” and, yes, it is fair notice for the men on the site who are using it only for hookups and one-night stands. But can’t people judge that depending on the person they end up on a date with? I’ve had dates where in the first three minutes I knew there was no possibility here for me romantically. But even in the best interpretation, “friendship first,” at least for me, implies months of activities when we are already pushing 70 and may not have too many months of activities left in our futures. Sexual intimacy with someone you connect with can be a great way to establish or discover connection. It’s not always about just getting laid.

4.     Many women just don’t know how to carry on a conversation. I know from painful experience that this is in fact also true of many men. Somehow the simple act of saying something, paying attention to the other person, asking a few questions, and actually being interested and curious have simply escaped them. Maybe it’s lack of practice. Maybe it’s nervousness. Maybe it's that they are so focused on finding a new man that, unintuitively, they want to talk about anything other than that. These have been my most frustrating dates, and I can spot the habit mere minutes into the (let’s call it a) conversation. They talk non-stop about trivia. They never ask a single question of me. I mean that literally. One woman (out of nervousness, she told me later) wanted to make the point that she had a better house and more money than I did. Another woman gave me a good 15-minute discourse on the travails of getting her winter tires changed over at Canadian Tire. Another one told me her favourite cuisine was hamburgers. You get the idea.

As I mentioned, this kind of conversation is just as common in men. Just try to observe your next conversation with a new person (romantic or not) that you’ve just met. How much do they ask you about yourself? How often do they practice what my friend Oscar calls verbal trampling—that is, interrupting you when you are in the middle of a sentence, usually so that they can say something about themselves:

Me: Yeah, I once spent a week in Lisbon and—

Them: Oh my God, my ex and I were in Lisbon like five years ago and we …

It’s exhausting.

My assessment is that good conversation requires only two simple ingredients: a sincere interest in and curiosity about the other person, and a willingness, even a desire, to listen to what they have to say, and to answer their questions about other topics.

5.     The other asspain about using dating sites is the dating sites themselves. I don’t trust them. They are full of fake and spam accounts which the sites make little effort to control or delete: they rely on you, on me, to find a scam and report it to them. Perhaps worse is that they allow long-abandoned profiles to remain in the system in order to give the illusion that there are many more potential partners available than they’re really are. I’ve even noticed with Plenty of Fish that when my matches have decreased and I go for a few days with no new prospects, miraculously several profiles appear which seem like good candidates. They may often be of women who have long ago left the site, I mean years ago, and have never used the profile actively for a decade. They are fossil profiles: in fact, at one of them, I found an anthropologist who specialized in the Middle Paleolithic era there excavating for signs of past human life.

It's been a couple of days on Plenty of Fish and I will continue fishing. Already had some nibbles! I’m hoping this time to pull up fewer old boots and rusty bicycle wheels.

And that’s all for this episode. Thanks for listening. A quick plea to rate or review me if you like the podcast … And, as always, please join me again next Tuesday.