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Once she discovered who she really was, and stayed firm in those convictions, it was easier to find love

January 20, 2023

In June of 2014 at 3:30 a.m., I decided to join J-Date, the self-proclaimed largest Jewish dating community worldwide, but it might have been the insomnia. George, my husband of 32 years, had died fourteen months ago and I wanted someone to have dinner with, to once again be asked, “How was your day?” Having found love before, I had no reason to believe it couldn’t happen a second time, but I was fifty and hadn’t dated since I was a junior in high school.

A couple on their first date. Next Avenue, dating advice widow, widowers
“Five years after my loss, I did find my second person online, but it took perseverance and an almost insane belief in the future.”  |  Credit: Getty

My first date as a widow was with a handsome mortgage broker who wrote great emails, but couldn’t stop lamenting about his past loves once we finally met in person. Worse, in my inexperience, I agreed to a second date after he promised to do better but he again spent our time acting like I was his therapist. He seemed surprised when I declined a third meeting.

Not knowing what I wanted, I made bad decisions about who to date and I didn’t trust my own instincts.

Things went downhill from there. There was the wealthy depressed artist with anger management problems, the overloaded climate activist who found fault with almost everything about me, and the polyamorous doctor who wanted to see me in rotation with many other women.

I tried other dating sites, but I still didn’t find my person. Many of my experiences were downright awful, from overly forward messages to last minute cancellations to guys who thought “come on over tonight and hot tub” constituted a reasonable first date.

I wasted so much time on men I wasn’t compatible with, including getting into a bad relationship that seemed less enervating than staying online.

I had such a steep learning curve navigating midlife dating. Here are some of the most important lessons I learned so you won’t have to.

Don’t Date Until You’ve Found Yourself

When George died, I lost not only him, but the “us” we were together and the “me” that was half a couple. I’d spent so many years thinking of “we” — where we liked to go, what we liked to eat — that it took awhile to find myself as an individual. I couldn’t really pick a new person when I didn’t even know who I was anymore.

An widow holding an old photo of her late husband. Widows, widowers, estate planning, Next Avenue


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Not knowing what I wanted, I made bad decisions about who to date and I didn’t trust my own instincts. Many guys had opinions about how I should live, and I took those criticisms hard because I was so lost.

It would have been far less painful for everyone had I waited until I was more sure of myself before trying to mesh with another person. So I recommend not dating until you’ve found your new self as a solo person.

Join Groups to Help Fight Loneliness

George and I had led isolated lives, he was an engineer and I a bookworm, so when he died I had few friends and no outlets for meeting people. If I wasn’t careful, I could go days on end without talking to anyone and, over time, my loneliness became almost unbearable.

Desperate, I joined the first groups I found: a car club and Rotary. Neither of these aligned with my interests, but the car club offered Saturday breakfasts and Rotary a weekly dinner, which helped with my solitary meals. Even better, I discovered that most people were welcoming to a new widow.

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