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Here's the Reason I Decided to Marry Again at 66

It all boils down to a great guy — and this.

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photo collage of happy couple surrounded by wedding rings, second marriage
David Weissberg (portrait courtesy Flash Rosenberg)
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Stepping off the mirror-lined staircase at Tiffany’s flagship store at 5th Avenue and 57th Street in New York City onto the third floor’s "Love and Engagement" department, Paul and I encountered a swarm of 20-somethings cooing over display cases aglow with megawatt bling.

Momentarily losing the composure earned through 66 years on the planet, I clutched Paul’s hand and asked: “Are they going to think we’re shopping for our grandchild!?”

A spry 69, Paul gamely endured my crushing grip, declaring: “You are the person I’ve wanted to share my life with since we met 38 years ago. I want you to have a ring you’ll treasure forever.”

At this stage, why make it legal?

Three weeks earlier, I’d never imagined myself strolling through this temple to aspirational jewelry, much less debating the finer points of carats, color, cut and clarity (the 4C’s defining diamond quality). However, I’d always known Paul was a 4C human — compassionate, caring, constant and communicative.

But in the early 1990s after four years together, we ran aground when I confessed to my Jewish parents that I had a secret Irish Catholic boyfriend.

Mom still wanted me to partner within our tribe even though, after three-and-a-half years of a tortured, straight-out-of-college marriage, I’d divorced the Jewish bridegroom who turned out to be psychotic.

For a few more months Paul and I limped along — ultimately capsizing along the shoals of our inability to figure out in which faith to raise the children. While I deeply grieved the death of our relationship, a piece of me wondered if my constantly questioning persona and Paul’s steadfast nature would have meshed well over the long haul.

Seven years later, despairing she would never see a grandchild, Mom wrote an apology letter which included this appalling phrase: “If I’d only known he was your last chance…..”

I settled into a mostly fulfilling single life — doing work that impassioned me first as a journalist, then a psychotherapist; creating a family consisting of friendships and other fulfilling exploits, such as accompanying a cargo plane stuffed with food and medical supplies to a war zone. I also had several passionate loves over the ensuing decades — but none of "forever" caliber.

Paul and I kept in contact through phone calls, social media and occasional lunches. However, when one of us was open to a second try, the other was unavailable. I often thought of Mom’s “last chance” prophecy.

By the time Paul and I rekindled our spark in 2015, he was 61 and I was 58. Both of us were childless, unattached and weathered by the loss of loved ones (my parents; his father and sister Diane). We shared a keen awareness that we could have a redo-life, and that it had a timestamp.

Having aged out of parenthood, and each having attained financial independence, a legal commitment seemed pointless. We were already an established couple. I was with Paul in Michigan at his mother’s deathbed, and he accompanied me to Berlin when I spoke at a summit of wellness leaders about how heartwarming it felt as a child of Holocaust survivors to be so warmly welcomed in Germany.

In March 2020, the pandemic shut down New York just as I received a stage 2 breast cancer diagnosis. Paul moved in to take care of me during treatment. Thankfully, the malignancy was dissipated. Thankfully, Paul hung in there.

In early November our beloved friend Joanna died after a five-month fight against metastatic pancreatic cancer. A few days later, Paul placed a Macy’s shopping bag on the coffee table. Wrapped inside red tissue paper nestled a jewelry box containing diamond studs which Paul explained represented his “intention” to propose.

“Yes, I will be your ‘Intended'!" I exclaimed, moving my prancing terrier Shea aside to kiss Paul, exclaiming, “Joanna guided you into Macy’s!” His response: “She’s smiling down at us.”

Joanna’s death brought home that with so much out of our control, it felt empowering to take charge of what was doable. This translated into Paul and I joining a pack of seniors choosing to say, “Until death do us part” again, after the death of a spouse or divorce. Indeed, according to the 2024 Gitnux Market Data Report, nearly half of people over 55 remarry.

And we didn’t go for a Tiffany’s ring. While it was fun play-acting Audrey Hepburn’s iconic diamond-dripping Breakfast at Tiffany’s gamine Holly Golightly ultimately, I preferred reality.

While it felt magical to view a fantasy ring, I wanted my symbol of eternal love to come from somewhere more mom-and-pop that better fit my coupon-clipping life.

At the start of the New Year, we selected my two-karat solitaire from a small Midtown manufacturer of man-made stones. “Laboratory-grown” diamonds are not only more environmentally friendly than traditional earth diamonds but they’re also plenty bling-y, and cost thousands of dollars less. I then told my husband-to-be: “When the ring is ready (it takes approximately one month), surprise me with a sweet proposal.”

On Valentine’s Night, after a candlelit meal of shrimp scampi and Prosecco, Paul presented me with dessert. Tucked into the bottom of a crimson red wine shopping bag overflowing with tissue paper was a ring box.

With Long and Winding Road thrumming from Paul’s iPad, he went down on one knee and asked if I would do him the honor of traveling with him down the road he desperately wished we’d taken 30 years ago. With zero hesitation, I whispered “Yes” and we began joyfully dancing our way, together, towards whatever will come next. We will be married later this month!

So I got the guy — and I got the perfect ring.

Have any of you married later in life? Let us know in the comments below.

Follow Article Topics: Relationships
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