Travels with Myself

A Journal of Discovery and Transition
Doug Jordan, Author

TWM – 36. Dating, Oh My

When Emily told me in May she was ending it with me she also said I needed to find somebody else, maybe my writing friend, go to California with her. (Was she being particularly cruel or did she genuinely think she was being helpful?) I knew that was a non-starter but I also knew she was right. I needed to find somebody else. But dating?

I had no enthusiasm for it – I still had hopes of Emily coming back (such is the state of obsessive grief!) –  but as the summer wore on with repeated disappointments, I knew I had to get on with it. 

I approached this problem with an admixture of wonder [of what might lie in store] and dread [of yet more rejection and disappointment]. I think that is the definition of awe, but it wasn’t inspiring me. It seemed more like a project than searching for romance; more like recruitment, procurement.

I investigated and signed up. (Why you might ask? – because of persistent sidebar ads on Facebook. What did Facebook know about my personal life? And how did they know it?!?) I didn’t post a profile and I didn’t subscribe, but Match started sending me daily temptations, and I ‘lurked’. But my heart wasn’t in it. And unless you activate your profile with a subscription fee, you can’t respond to those invites.

When Emily ended it for the fourth (and last time) in August I knew I had to act. It wasn’t rational, I know, but I just wanted this angst over, not just the pain of loss but the fear of loneliness. I felt I was in a race to find happiness again, or maybe for the first time. I was in a race to live my remaining years with a constant companion, and with eros, and maybe realize a few dreams. For that I needed to get out there and face the dating scene. I had some friends, mostly women, who argued living alone had definite advantages, but I wasn’t buying that[1].

I know it is a cliché but dating is hard late in life, especially for me since I had very little experience of it as a teenager. But I persuaded myself I had developed a few social skills since I was a teenager, I knew a lot of women from my professional life, and I had had a lot of lunches; I knew how to engage women and nurture a relationship. But those were all professional encounters, or fantasies; this was more consequential, more risk – rejection, and failure.

I preferred ‘organic dating’ – going out with people I already knew, if only slightly, or be introduced to somebody – but I knew the name of the game in 2018 was on-line dating. Kinda like a lottery – if I wanted to win a prize I had to buy a ticket – and maybe just as soul-destroying. I took a deep breath and posted my bond and my profile on I wish I still had a copy of my profile though I’m sure if I post another bond, Match can retrieve it for me! I set my criteria to Caucasian women, age 45 – 70, within 150 km of Ottawa. I’m pretty sure my profile was sober, somber and cerebral – who would want to date a recently widowed man of 71, seeking an intellectual slim blond who also loves the CFL? Not many 45-year-olds answered my call. Nor many 50-year-olds, nor even 60-year-olds. I realized in my arrogance (and fear?) that I might wait a long time if I thought they would make the first move, so I started complimenting their pictures with some clever remark. Attracting them with my intellectual prowess and sense of humour.

How successful do you think those strategies were?

Despite of the dearth of responses, I did get a few dates, some of them very promising. A few even made it to 3rdor 4thdates.

Cynthia was my first hit in the week after Emily’s bomb and my post on Typiclal of this on-line dating thing, as I learned, you start by text through the site, then exchange cell-phone numbers and begin texting that way, then eventually to actual talking. She was blonde, hair styled in a classic cut, trim figure, age 63! She had been Miss Tulip festival in 1973, and Miss Ottawa Rough Rider the following year – A Rough Rider cheerleader, and even understood the game! And she had dogs! Her opening salvo when we first exchanged on Match, ‘Coton de Tulears rule.’ ‘Nonsense’ I said, ‘Standard Poodles.’ I told her all about the pathetic Emily story. Maybe that was my second mistake. But she invited me to lunch on my birthday, even gave me a nice card, and a package of tissue! We went to a RedBlacks game four days later, a date I had promised Emily. I picked her up at her west-end townhouse, got introduced to her cuties (the Cotons!) and then to Patty’s Pub for a pregame libation and a little dinner. Cynthia certainly was at home, and she liked her vodka. We missed the first quarter. I’m not sure of the RedBlacks won that game but it was enjoyable and I didn’t even have to explain the plays to her. We repaired to Patty’s after the game for a fancy coffee, or two. I drove her home around 1:30. She didn’t invite me in (no doubt to keep the dogs quiet (and I wouldn’t have gone)), but I did enjoy a nice big wet kiss goodnight. ‘I can do better than that,’ she told me. I drove home thinking maybe there was life after Emily. We didn’t agree on politics – Liberal Red/Tory Blue – and she was historically challenged. We came a cropper on the phone Saturday night. She hung up on me. I brought her flowers the next day but she wouldn’t answer the phone and I couldn’t rtng the doorbell because of those blessed Cotons so I left the bouquet on the porch. She did text me later. She said I had some issues – sexist, racist, and a few other -ists I don’t recall. Damn.

My relationship with my organic friend from Saskatchewan lasted several months – movies, meals, Mexico City. I really liked her, and she was very tolerant of me and my mental state. Compatible values, love of the CFL (except for the Rider green part), good intellect, but no sexual chemistry. Physical attraction may be hard to defend but for many (I’m glad to know It’s not just me), it is crucial.

I pursued, Andrea, a hard-working dark haired beauty, a former client and lobbyist in bureaucratic Ottawa and now a proprietor of a business up the Valley. Compatible politics, but too many gaps – she gave me no encouragement. 

Match generated quite a few coffee meetings, sometimes lunch, but mostly non-starters. A poodle woman from Richmond who accepted my books but not my wit. A Carleton (adult) student who had little to show for her studies. A golfer who was to meet me for lunch at her club, but never showed: Or maybe she observed me from a distance and concluded I wasn’t a match. How did she know I hated golf? A lobbyist for lunch at my favourite restaurant downtown; she was deep into the Ottawa political scene and talked the whole long lunch. Maybe I couldn’t stand the competition. My waiter friends gave her the thumbs down.

I met Patricia from Bath at a restaurant in Kingston. She showed a lot of promise: an author and consultant herself, an MBA from Ivey School of business don’t you know, and a card-carrying Conservative. And a fundamentalist new-age Anglican. We had already conversed about my state of mind and the second thing out of her mouth as we greeted each other were, ‘you wouldn’t be so depressed if you had a personal relationship with Jesus Christ. Agnostic Unitarian Doug did his best to explain, as diplomatically as he could, Unitarianism to this ignorant educated woman. She knew nothing. She ordered Arctic Char for lunch after I explained that to her as well.

I met Maggie through a friend – maybe these personal chance encounters would bear better fruit. She was a high energy European who ran a flower shop. Quirky, sexy, age ?45? She didn’t like chocolate and there was no point in bringing her flowers, so I brought her popcorn to her shop. She was surprised for my surprise visit, and probably the popcorn. I think she was flattered and pleased, but also perhaps a bit taken aback but my approach. Does this only work in the movies? But she had just broken up from a long-term relationship. She wasn’t ready, and I guess she had more time than I did. She promised she’d set me up with a good friend of hers. She never followed up., a sister internet site to, produced Francine, a wonderful retired lawyer from Gatineau; pragmatic, sly sense of humour, in both official languages, she even encouraged my cigar aficionado claim. But there were issues, health and no chemistry for me. ‘Lets just be friends,’ I suggested. And that’s what we did, cultivated a friendship with many dinners and lunches over six months. I think we’re still friends.

And then another Cynthia, a PhD psychologist, blonde, slim and sexy, age appropriate. I’d even met her in a previous life when she was a search consultant for a high priced international firm. She had been five times married and had recently retired to Florida. I told her I had good friends in Naples. But after some scintillating conversations on Saturday and Sunday night as our plans were shaping up, she sent me a text Monday morning – she judged that I didn’t have the means and the flexibility to match her life-style needs. Maybe she was right but I thought I should be the one to determine that. With my hair on fire and a modest bank account, I thought I could keep up for five years. I wondered what had happened to the other husbands.

[1]I was almost a cliché, I admit. ‘Studies have shown’ that married men are happiest, followed by single women!; least happy, married women.

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