He Slept With the Housekeeper, and I Woke Up in Ancient Greece

A past-lives reader once told me that I hadn’t had a good relationship since ancient Greece. I remember thinking, “I knew I was in a slump, but wow.”

This reading was somewhere between Marriage Number One (in which, two years in, my husband realized he was gay) and Marriage Number Two (in which, 14 years in, my husband realized he was just not that into me).

Apparently I’d been a woman in every lifetime (rare) and I could have children if I wanted (I’d had plenty of children over the centuries)—but my job in this lifetime was to learn to love and be loved.

That reading was a gift…only in that it was gifted to me by a friend. Otherwise, it was a curse, because as I waded through the rubble of yet another breakup—deleting travel plans from my calendar, putting photos in a folder I won’t stumble upon daily—I am coming to terms with the idea that this lifetime might be a wash.

That’s hard for an optimist to admit.

I am also coming to terms with the idea that I might no longer be qualified to be an optimist. Because here I am, in my fifties, after writing two books about relationships, having my own relationship column in both Glamour and O, The Oprah Magazine, and writing five seasons of Sex and the City, reeling from a breakup that caught me so off-guard it might have put me off dating forever. I feel like I’m going back to square one.

And I was going back to square one. I was about to spend a week in ancient Greece.

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“I care about your toe, but I care more about your heart.” That’s what the sympathetic female orthopedic doctor said when I tried to explain why waiting to go to Greece until after my broken toe healed was not an option.

It wasn’t easy to explain. I felt as if the friends, family, and Facebook community who’d been watching the Cindy Chupack show for the past three-plus years about a recently divorced fiftysomething who met a great guy on a plane from New York to L.A. right before the pandemic would be left feeling confused and shortchanged, kind of like the people who made it all the way through Lost.

My relationship had become a success story that friends told other friends who were divorcing (“You’ll be fine! Just look at Cindy!”), mostly because of its Nancy Meyers-esque aspirational rom-com trappings. A bicoastal romance full of weekends at his penthouse Brooklyn apartment, weeks at the 1865 country house he bought upstate, Pinot Noirs from his wine cellar, fresh flowers from his garden…

“He might be the first grown-up relationship I’ve ever had,” I’d announced gleefully to my therapist. “It’s so nice to be with someone who takes care of me!”

And he did. He made travel reservations, cooked delicious dinners (and cleaned up afterward!). He even had an architect drawing up plans for a writer’s studio for me in one of the old barns on his property.

And then there was a sad side I only shared with my closest friends. Over the past year, I’d supported him through the sudden death of one of his children. It wasn’t my tragedy, but seeing someone you love endure pain of that magnitude is probably the hardest, saddest thing I’ve ever experienced. It was impossible to imagine that there would be anything we could not survive as a couple until the unimaginable became reality, and our relationship ended as suddenly as it began.

“I just found out my boyfriend of three-plus years was sleeping with his housekeeper for the last two and half of those” often raised more questions than I wanted to answer. (His housekeeper? How did you find out? Did you confront him about it? Did you have any idea? Was she still cleaning his house?!)

On the other hand, saying I was dealing with something I didn’t want to discuss had a group of my friends certain that I had cancer.

The fact that I was going through a breakup didn’t seem to capture the shock and awe of the situation, like the texts the woman had shared when I’d asked for proof of their romance, which included a picture she’d taken of the two of them in the vintage convertible he’d recently bought—the one in which I pictured us driving off into the sunset, the one I hadn’t even had a chance to ride in yet, the one that prompted me to say, “I’m so glad you’re doing something for yourself.”

There were other texts, but I think I blacked out.

And now I was in an orthopedist’s office because in the fog of those first few days, I missed the bottom stair and broke my toe.

I felt like a walking Cathy cartoon by this point. I had a broken toe, a broken heart, and a full calendar for the rest of the month that included, among other things, figuring how to break this news to my 12-year-old daughter, Olivia, without making her distrustful of men for the rest of her life. I decided to tell her the breakup was mutual, to which she replied, “So you were calling him to break up and he was calling you?” It’s a fair question. (“I couldn’t help but wonder,” Carrie Bradshaw would type, “is any breakup really mutual?”)

Then there was the trip to Dallas to help my aging parents. An emotional breakup that you’re trying to avoid can help you be very dispassionate about other things you might normally avoid, like talking to your parents about the cost of long-term care, and their feelings about cremation versus burial.

Our dirty family secret (until now, I guess?) is that my sister and I have been supporting our parents for decades, because my dad (who was ironically an accountant) seemed to have “Buy Lotto Tickets” as his retirement plan. Supporting the men in my life and somehow being resented for it was a pattern I’d repeated up to and including my last marriage, and it was something I was thrilled about not doing for the first time with this last boyfriend. He’d even offered to pay for half of the breast reduction I was considering…so, I guess, for one boob?

That was another thing I had to do. The breast-reduction consultation.

I’d waited four months for this appointment, but immediately after I took my “Before” pictures, I broke down and said I wasn’t sure what breast size I wanted since the boyfriend I thought I was getting old with was no longer in the “After” picture.

Somewhere between that and my high school reunion (yes, I had a high school reunion too!), I found myself just wanting to be quiet. To be someplace where I didn’t need to answer questions, or put on a brave face for my daughter, or disappoint my four-month-old puppy who just wanted to play.

Did I mention the puppy? Even fully grown, she would still be small enough to travel cross-country with me to see the boyfriend I no longer had. Sigh.

My heart, and my toe, just needed to heal.

That’s how I found myself on a website called Healing Hotels of the World (which is full of places so beautiful it makes you want to have a tragedy every three months). And the hotel that spoke to me, called to me really, was Euphoria Retreat.

Not only was it gorgeous, but they had a new program called Inner Emotional Harmony specifically for traumatic life experiences that, according to their website, “allows for the release of negative emotions and bitterness whilst leaving you armed with greater resilience to deal with whatever difficult trials you may be facing.”

It wasn’t until after I’d started to book the trip that I realized Euphoria Retreat was in Greece, where 3,000 years ago, I had my last good relationship.

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When I arrived at Euphoria (a two-and-a-half-hour drive from Athens) and was greeted in its beautiful, airy reception area by warm smiles and cold, oregano-infused water, I wondered if I was already healed.

Then I discovered the indoor Sphere Pool, which had a sliding glass door in the pool to the outdoor pool, and a central sphere where you could float, looking up at a skylight, while listening to the underwater sounds of dolphin and whales. I spent so much time floating there that, if I had another week, I think I’d be able to understand what they were saying.

Around the central sphere were all different kinds of hot tubs that, to me, were like a metaphor for the entire Euphoria experience, because you have no idea what is going to happen when you push a button in this funhouse/Russian roulette of water jets. One hot tub is like a chaise lounge, and bubbles rise up and surround you. One button activates a powerful shower that, if you don’t turn around immediately, pelts you in the face. But the one that really caught me off guard was the standing hot tub where, upon pressing the button, a geyser explodes underneath you.

That geyser was one of many things I didn’t see coming on this healing-while-reeling trip. But unlike my breakup, I started to look forward to the surprises that every room, treatment, pool, and person seemed to have in store.

Although the Inner Emotional Harmony program was described in a notebook I was given, the combination of ancient Greek, Chinese, and modern medicine was so new and mysterious to me, I was never sure whether what I had scheduled required me to be in a swimsuit, regular clothes, or a robe, and whether I would be talking, floating, getting massaged, or just relaxing while my chakras were being cleared.

Despite this constant confusion about what I was doing next (or maybe because of it), I have never felt more relaxed. I couldn’t anticipate or control anything. All I had to do was show up.

The only treatment I felt like I survived rather than enjoyed was the Hydrotherapy Multi-Sensory Experience. That was partially my fault, because when the therapist asked if the water temperature was good before she started this high-tech treatment, I said it was (I like hot showers), but I didn’t realize what a hot shower would feel like if you were horizontal and the water went on and off unpredictably for 20 minutes. There was no changing the water temperature once it started—believe me, we tried—but I kept thinking I’d get used to it, or that it was about to get better. Which is my problem in relationships! In fact, I found myself thinking about all of the men in my life who had disappointed or hurt me, thoughts that had not come up during my more relaxing treatments (which would be any other treatment), so maybe even my least favorite treatment was useful because I will now relate that horizontal hell with people who make me feel unwanted pressure, helpless, and trapped.

On my last day at Metaphoria (as I started to call it), I finally had my “Anger Release” session, which, disappointingly, didn’t involve yelling or breaking anything. It was a treatment more generally for the “release of trapped emotions,” which turned out to be part talk therapy, part guided meditation, part tapping a magnet on my spine and seeing which way I leaned (toward or away) from certain ideas.

My guide was Mary, a lovely presence, who told me the trapped emotion I needed to release, it seemed, was my fear of being alone.

That didn’t resonate with me at all. I explained that I was relieved to be alone for the moment, that this last breakup had leveled me in a way that even my divorces had not, and that I was tired, and hurt, and tired of being hurt. I said I couldn’t seem to express anger, or even feel anger on a gut level, even though intellectually I knew I was angry. I said my anger always came out as sadness. Then I started to cry, as if to illustrate the point.

And I said I didn’t know how to mourn a relationship that I’m not sure I had with a person I’m not sure I ever knew. And I was worried that what made him so different from every other man I’d ever dated—the fact that he didn’t need me for financial support—was why he felt entitled to be so reckless with my heart. Was it male privilege at its worst?

That was all painful to admit. But the hardest thing to say aloud to Mary was how I felt like he stole my hope, and I didn’t want to do this again.

I didn’t want to try again.

Which meant I might spend the rest of my life alone.

Mary was right. I was afraid of being alone.

And the guided meditation she gave me to put on my phone and take home was so comforting that I still think of it (and sometimes listen to it) almost every day.

She said, in her calming Greek accent, that there was a star above me, shining light down, and a little earth below me, shining light up, and this formed a bubble of light, like a sphere (like the Sphere Pool!), and I could decide who to let in, and I didn’t need to do anything. I could just be.

That hadn’t occurred to me, that I didn’t need to “try again,” that I could just live my life and see who came along. I felt myself exhale for the first time in a month.

I started to imagine everyone who was making my life hard outside of this bubble, talking as if they were on mute. Their mouths moved but I couldn’t hear them. They could reach for me, but couldn’t get in.

And then I imagined gently bouncing safely through the air in this bubble—over mountains, over waterfalls, underwater—and I realized that, of all of the people in the world, my daughter Olivia was the person I would want next to me on this ride. We would laugh at the same things and be in awe about the same things, and maybe that’s all love is: It’s who you would want with you on the most amazing ride you can imagine—and that ride is life.

I was afraid I’d forget that idea as soon as I left Greece, so in the airport on the way home, I bought a bracelet with a glazed ceramic charm that looked like a bubble inside a bubble to remind me I get to choose who to let in. And that whether I’m alone, or with Olivia, or with someone else one day, I still get to be on this ride, and it’s beautiful and breathtaking, and full of wonder. And like Metaphoria, you don’t know what will happen, and that’s part of the fun.