Love and romance: Part II

Bob Dylan wrote “The Times They are a Changin’” and that was certainly true in the dating world. I knew people who found a partner online, mostly 30 something’s, and decided to give it a try.

I researched dating sites the way I used to research stocks, with the same confidence that I’d make an “ informed” decision. I started with JDate and Our Time, but they were each too limiting — my religion is hugely important to me, but it only mattered that the man I chose respected it, and the “senior” dating sites were depressing — I didn’t want age to be our common denominator.

I then did a “trial run” on and that seemed ideal for me though it was not totally reliable, not always credible, certainly not algorithmically accurate, but replete with SO many good selections.

It’s challenging to create a profile, and I was wary of revealing too much but wanted to be clear about my negotiables (religion, career, education, widowed/ divorced, children) and non- negotiables (politics, sense of humor, motivation, compassion). I made sure my photos were recent and relevant and highlighted my career, travel, sense of humor, independence, focus on social justice, and total DIS-interest in sports. I provided my first name but was vague about other details (employer, alma mater) which would make me easy to Google.

Fortunately I was a salesman for 40 years and could handle rejection, because it came fast and furious. I initially contacted many men but so few got back to me; I reassured myself that it wasn’t “personal” — they didn’t even know me. It made me wary of continuing, (although I was in the City and had four dates the first week which felt like a good start, including two dates with one man). I recognized the challenges with online dating, encountering more problems than solutions: one man asked to see me again and ,when I readily agreed, told me he had a girlfriend but she worked evenings; another had NO internet presence and implied it was because he worked for a high level secret government agency. I realized quickly that I had to learn to manage expectations, and, as the saying goes, trust but verify.

A week later Covid started, I moved to the country, and everything changed — I could chat but not meet anyone. I learned to avoid crazies, phonies, predators, men who were unsuitable, and just took my time. I learned to ask last names so I could Google them, and insisted on FaceTime to confirm who they were. I expected to return to the City after Covid, and “met” a man who seemed perfect — highly educated, funny, sensitive, and we FaceTimed daily for months until we finally met in person. All the indications were perfect — we even predicted Match would use our narrative in ther ads — but he was really tied to the City and had zero interest in the country — confirmed when he spent a weekend and couldn’t wait to get on the train home.

After a few more dates (in the city!) I ended it.

I was clearly better off dating locally (and maybe Boston and DC), and that first summer primarily dated a retired engineer who had taken up watercolor painting — we had wonderful dates visiting every outdoor sculpture park we could find, but having lived with a fabulously talented artist, I frankly couldn’t “relate” to this man’s work, let alone live with it.

I spent a year dating men from Match and never had a really bad date, but during online chats came across one fellow whose ex-wife had a restraining order against him; another who described himself as a petroleum engineer and gemologist, and I discovered he was wanted for swindling a woman he met online out of $75,000; one who turned blatantly anti-Semitic when I suggested we weren’t a great match; one was described himself as “gender fluid” and told me if we were to meet he couldn’t guarantee he’d come dressed as a man; and one who sent me home from our FIRST date with a draft of his autobiography. That said , I also met several lovely men who were just not what I was looking for.

Please reach out to Gwen with your thoughts or questions at

Gwen lives in Pine Plains with her partner Dennis, her puppy Charlie, and two Angus cows (who are also retired!).

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