Willing: A Series on Dating, Sex & Life for Grown ups

Dating is so complicated at this stage — on top of all our scar tissue from umpteen years of living and loving — we’ve got the usual nerves and butterflies. Not to mention the practical obstacles of lives with baked-in structures, demands and impediments. Too often, we just can’t break through. But sometimes we do.

Willing: Dish Stanley and The House That Jack Built by Lisa Ellex

In this installment, writer Lisa Ellex talks with Dish Stanley, who reflects on one particular dating experience and offers her advice on what we should leave behind before approaching the dating table.

“Jack and I met in the city. After the passing of my husband, Jack was the second or third person I met on a dating app. He had been divorced a decade, had an apartment in the city that he crashed at a few times a week but – because he ran his own company and had flexibility – where ‘he really lived’ was his home by the ocean in Stonington, Connecticut. Jack stayed in Stonington most of the week and all of the summer, having owned it for forty years. Prior to his divorce, it was the place where he and his family (kids and ex-wife) had spent their summers and holidays during the course of his marriage.

In the midst of a lovely second date at Jojo’s on the Upper East Side of Manhattan, the conversation turned to the respective paths of our lives, what we were each reading, and how we liked to spend our weekends. It was then that Jack said, ‘Whoever I partner with needs to want to — now or eventually — have Stonington, and my home there, as our primary residence.’

‘Oh, I’ve never been to Stonington,” I said, “but I have a friend a couple towns over in Westerly, Rhode Island and it’s a lovely area.’

Jack continued. ‘I know from experience that my partner will want to make it her own if it’s going to be her primary residence, too, but I’ve been through this already and it doesn’t need much. I could see replacing the throw pillows or something but …’

I thought that this all seemed like an awful lot of ‘staking his ground’ much too soon but, clearly, Jack felt the need to hint at some past irreconcilable dating conflict for him.

Later in the date, when we were talking about places we loved to go, Jack casually mentioned that for the last decade since the divorce he spends the Christmas/New Year holiday in St. Barts, where he rents a large compound with his ex-wife and children. This vacation situation was the logical solution for Jack’s family. With bedrooms on each end of the house and a kitchen and living room in the center, Jack and his ex-wife could maintain their privacy yet commingle with their respective kids in the common space as they pleased (or not). All was well. And then came Fred, the ex-wife’s soon-to-be-husband. A flexible fellow, Fred had no problem with being added into the family mix.

At the end of the date, as we were getting up from the table, Jack asked me what I was doing over the weekend. It was a Thursday night and he was heading out to Stonington for the weekend. I said that, actually, I was visiting my friend DiAna and her husband, Ken, in nearby Westerly. On the spot, Jack invited us to stop by for a coffee or drink. I happily accepted his invitation, since it was a chance to see this house that was such a deal-breaker for him, and told Jack I was excited to see the little beach house he loved so much.

‘It’s not much,’ Jack said. ‘It’s been the same for years, actually. And everything is original to the house. It’s classic, really.’

After telling DiAna and Ken about the whole conversation with Jack and his ‘throw pillow’ comment, DiAna saw what was at stake. She reorganized our dinner plans so that she, her husband and I could stop by Jack’s for a drink before the three of us continued on to dine nearby, and I spent the next few days enjoying visions of a classic New England seaside cottage where Jack and I could spend weekends curled up in front of the fire and enjoying each other’s company. I could not have been more mistaken.

DiAna, Ken and I rode up to Jack’s house excited with anticipation. But after eyeing the rundown Cape, Ken – who doesn’t hesitate to speak hard truths – blurted, ‘You’ll never live here, Dish. Why even go in? Can we abort immediately and catch the end of the Red Sox game at the bar before dinner?’ Unfortunately, Jack had seen us in the driveway and was already out on the porch. With Jack as our escort, we reluctantly parked our bikes and entered to find a time capsule, circa 1972. Just when I thought nothing could top the matching pea green couch and drapery, the wood paneling, the dark floating kitchen cabinetry, and peeling formica countertops, a visit to the bathroom proved me wrong.

Against a backdrop of pink and gray tile, a coordinating suite of bubblegum-colored toilet, sink, and bathtub sat atop a worn linoleum floor. As I sat on the toilet, I braced myself, certain that Sonny and Cher would jump out of the shower to sing a chorus of ‘I Got You Babe.’ When I came back out, Ken gave me a look to remind me that the Red Sox were waiting. We politely excused ourselves, thanked Jack for the visit, jumped back on our bikes, and peddled our way back into 2015.

And right then I realized that if Jack was a man with whom I would have to pick my battles, I would have no choice but to surrender to ‘The Battle of the Seventies Beach House.’ But hard as I tried to give in to the adventure of it, it felt like a big defeat - not just uprooting myself and my life in the city to this lovely but sleepy little beach town — but also to living in the little beach house with its pea green couch that his ex-wife had decorated decades ago.

The next time Jack called though, he brought up St. Barts.  Already having finalized the family’s plans to spend the upcoming Christmas at the St. Barts house with his kids, his ex-wife, and Fred, he already wanted to know whether — if we progressed — joining them was a possibility. Candidly, I told him that if things progressed between us I’d be open to the arrangement every other Christmas, but probably not this one, as I had promised my octogenarian parents that I would be celebrating my holiday with the whole family in their home. And with that, Jack announced that that would be a deal-breaker for him, as he had no desire to be the third wheel for his wife and her partner.  And that’s when it was clear: Jack would never be the Sonny to my Cher, the Steve to my Eydie, or the Captain to my Tennille.  And with no desire to be with a man who could not respect my relationship with my own family, not to mention my living preferences, the way he demanded that I respect his, I closed the door on Jack and his 1970s beach house, belting out Nancy Sinatra’s ‘These Boots Were Made For Walkin’ all the way home.”

Are you Willin’? If you’ve got your own later-in-life dating story to share, write me at Dish@PrimeCrush.com. If you don’t want to write it yourself, you (like Dish) could share your story with Lisa Ellex and she’ll write it.

Willing: A Series on Dating, Sex & Life for Grown ups

“A girlfriend sent me a text last week saying she had a very special man she wanted me to meet, so I replied “sure!” Minutes later I got a text from an unknown number saying “my dear friend Susan said we should meet. Tough to ignore Susan—she’s so often right.”

Mike and I had dinner Wednesday. We got side-by-side seats at the bar for a drink first. The bar was crowded and we were getting jostled a bit but I noticed that whenever our legs brushed up against each other he jerked his back as if he’d just been electrocuted. Jarring! Still, we ended up in an easy, lovely conversation when we ended up seated across from each other over dinner.

When he walked me home he slipped my arm in his and said “I have to tell you something. My girlfriend of four years died of cancer three months ago. I took care of her for the last two years of her life. All the appointments, everything. This afternoon I had a little breakdown and considered canceling dinner, but I’m so glad I didn’t. I’m sorry if I seemed shell-shocked at first.”

The next day Mike sent me a text with “all the usual” thoughtful thank you’s and things to say. And he wrote this: “I’m still grieving, but I’d love to stay in touch and get to know each other better. As my life becomes grooved, who knows? In the meantime, you’re such a big reader, perhaps we could start by discussing some books?“ When I went to my front door the next day I received an Amazon delivery of Erik Larsen’s new book The Demon of Unrest. He’d remembered that we’d both said over dinner we were eager to read it. And later, I got a note saying ”How about discussing Demon sometime after Labor Day?”

Got a dating story — funny, not funny, touching, awkward, fabulous, other? We’d love to publish it. Don’t want to write it? You can tell it to Lisa Ellex and she’ll turn it into poetry. Write to her at LisaEllex@gmail.com.

The Crush Letter
The Crush Letter is a weekly newsletter from Dish Stanley curating articles & intelligence on everything love & connection - friendship, romance, self-love, sex. If you’d like to take a look at some of our best stories go to Read Us. Want the Dish?