Love and romance, swiping left or right

Johnny Lee recorded “Looking for Love in all the Wrong Places” for “Urban Cowboy” and that seems like the perfect metaphor for dating at this stage of life.


When most of us first entered the dating world several decades ago, we met each other at parties, college, where we lived, the gym, bars, or while shopping. I met my first husband at a small menswear store on the Upper West Side, although for the life of me I have no idea what I was doing there, and I recall one fellow I met in line waiting to vote — he worked for the FBI and I remember every time he came into my apartment he took off his gun and my biggest fear was that the cat would somehow get to it !

I met my late husband at the gym — that was really the ideal place to meet although I joined it simply because it was nearest to my office — it was in the World Trade Center, where all of us Wall Street crazies arrived when it opened at 6 a.m. We found ourselves on adjoining treadmills (along with then Mayor Ed Koch), progressed to running across the Brooklyn Bridge together, and what ultimately ensued was a glorious 37 years! Not surprisingly, that pushed many of my girlfriends to join a gym; as a bonus, I also met some women who have become my dearest friends over the years.

Dating was easy, frequent, often casual, challenging, and sometimes led to heartbreak, but for most of us, it was part of the process of finding a spouse, of meeting THE person we thought we could spend the rest of our life with. We had very definite rules and tended to judge each other critically — would our friends like the person, would our parents, did we agree on everything, were we similar in every way imaginable, and could we finally STOP dating and get married.

Fast forward to 2020 after my husband’s passing and I realized I could have a wonderful life flying solo, but I wanted to try dating again. I was still living in the City, and anticipated meeting someone “organically” at dinner parties or at the gym (again), at benefits or at the bookstore, through business or volunteering. I assumed it would be as simple as it had been 40 years before, but I was SO wrong. For starters, I didn’t have the energy to go out all the time, let alone “flirt” as I used to, and I wasn’t even sure what that would look like at this stage of life. A friend once complained to me that men no longer looked at her on the street, and I pointed out that men still looked at me, but they were just much older than I remembered!

There was always the possibility of being “fixed up,” but in a world where single older women far outnumber single older men, the likelihood of that declined with each passing year. A friend mentioned a man she knew in Boston who was recently widowed and she felt confident we would really hit it off. He suggested we Face Time, and when we did I thought he was delightful — attractive, intelligent, charming — he told me after about a half hour that we weren’t suitable for each other and ended the call rather abruptly. I was stunned, and deeply offended, but it was a fast preview of what dating life could become. I no longer had the energy to look my best every day, to sign up for classes where I might meet someone, to be the extra person at a dinner party of married couples, to travel alone, and to check on whether or not a man was wearing a wedding ring (which I realize that many of us who are widowed, often still do for some period of time after our spouse passes away).

I needed a new way to meet men, and in upcoming columns will discuss online dating — the ugly, the bad, the good and sometimes you just hit the jackpot!

Please reach out to Gwen with your thoughts or questions at GwenG@millertonnews.com

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

The views expressed here are not necessarily those of The Lakeville Journal and The Journal does not support or oppose candidates for public office.

Latest News

Wake Robin Inn sold after nearly two years of land-use battles

The Wake Robin Inn in Lakeville has been sold for $3.5 million following nearly two years of land-use disputes and litigation over its proposed redevelopment.

Photo courtesy of Houlihan Lawrence Commercial Real Estate

LAKEVILLE — The Wake Robin Inn, the historic country property at the center of a contentious land-use battle for nearly two years, has been sold for $3.5 million.

The 11.52-acre hilltop property was purchased by Aradev LLC, a hospitality investment firm planning a major redevelopment of the 15,800-square-foot inn. The sale was announced Friday by Houlihan Lawrence Commercial, which represented the seller, Wake Robin LLC.

Keep ReadingShow less
Kent commission tackles Lane Street zoning snag
Lane Street warehouse conversion raises zoning concerns in Kent
By Alec Linden

KENT — The Planning and Zoning Commission is working to untangle a long-standing zoning complication affecting John and Diane Degnan’s Lane Street property as the couple seeks approval to convert an old warehouse into a residence and establish a four-unit rental building at the front of the site.

During the commission’s Feb. 12 meeting, Planning and Zoning attorney Michael Ziska described the situation as a “quagmire,” tracing the issue to a variance granted by the Zoning Board of Appeals roughly 45 years ago that has complicated the property’s use ever since.

Keep ReadingShow less
Kent P&Z closes High Watch hearing, continues deliberations

Kent Town Hall, where the Planning and Zoning Commission closed a public hearing on High Watch Recovery Center’s permit modification request on Feb. 12

Leila Hawken

KENT — The Planning and Zoning Commission on Feb. 12 closed a long-running public hearing on High Watch Recovery Center’s application to modify its special permit and will continue deliberations at its March meeting.

The application seeks to amend several conditions attached to the addiction treatment facility’s original 2019 permit. High Watch CEO Andrew Roberts, who first presented the proposal to P&Z in November, said the changes are intended to address issues stemming from what he described during last week's hearing as “clumsily written conditions.”

Keep ReadingShow less
google preferred source

Want more of our stories on Google? Click here to make us a Preferred Source.

Kent committee to review Swift House options

The Swift House in Kent has been closed to the public since the COVID-19 pandemic. A newly appointed town committee will review renovation costs and future options for the historic property.

Alec Linden

KENT — Town officials have formed a seven-member committee to determine the future of the shuttered, town-owned Swift House, launching what could become a pivotal decision about whether Kent should invest in the historic property — or divest from it altogether.

The Board of Selectmen made the appointments on Wednesday, Feb. 11, following recent budget discussions in which the building’s costs and long-term viability were raised.

Keep ReadingShow less

Kathleen Rosier

Kathleen Rosier

CANAAN — Kathleen Rosier, 92, of Ashley Falls Massachusetts, passed away peacefully with her children at her bedside on Feb. 5, at Fairview Commons Nursing Home in Great Barrington, Massachusetts.

Kathleen was born on Oct. 31,1933, in East Canaan to Carlton and Carrie Nott.

Keep ReadingShow less

Carolyn G. McCarthy

Carolyn G. McCarthy

LAKEVILLE — Carolyn G. McCarthy, 88, a long time resident of Indian Mountain Road, passed away peacefully at home on Feb. 7, 2026.

She was born on Sept. 8, 1937, in Hollis, New York. She was the youngest daughter of the late William James and Ruth Anderson Gedge of Indian Mountain Road.

Keep ReadingShow less
google preferred source

Want more of our stories on Google? Click here to make us a Preferred Source.

google preferred source

Want more of our stories on Google? Click here to make us a Preferred Source.