Family Matters

The Art of Dating Your Ex

A Therapist Finds Love Where She Least Expects It

Alissa Hirshfeld
Magazine Issue
July/August 2023

Over Christmas, while watching Encanto, my college-aged daughter squeezed my hand and whispered, “Bruno is Dad!” These words started me on the long, humbling process of reconciling with my ex.

In the movie, Bruno is a truth-teller who hides in the bowels of his intergenerationally traumatized family’s magical house after predicting one too many catastrophes. Because so many family truths have been buried, including Bruno’s very existence, the house begins to crack. Bringing Bruno back into the fold is the only way to repair the family’s magic.  

Up until the last six months, my daughter’s only contact with her father had been over text. At the end of my relationship with him, he’d demonstrated manic symptoms that had scared her. A brilliant, creative man, my Latino ex has often been misunderstood. At times, his visions, theories, and pronouncements verge on paranoia, but eerily, they’ve also turned out to be prescient on more occasions than I can count. 

“Lis!” he called out, sitting bolt upright in bed on the morning of September 3rd, 2001. His face had been pale and agitated in the dim light of our bedroom. “I had a terrifying dream! Towers were on fire. People were jumping. There were sirens. Something bad is coming, I can feel it.”

He’d grown up in an abusive, alcoholic home, which at one point had caught fire. I interpreted this dream as a working through of his own childhood. Then, a little over a week later, 9-11 happened.

In the darkened movie theater, my daughter’s words took me off guard, and tears streamed down my face. After dropping her at our condo, I returned to my car, took my phone from my purse, and dialed my ex. 

“Are you okay?” he asked. A question about our daughter followed. I rarely called, so it made sense he might think something was wrong.  

“We’re fine,” I said, “We just saw Encanto.

I could hear him exhale.

“I want to heal our family,” I blurted out. Then I began sobbing, not fully understanding why. My cheeks were hot. My heart pounded with a mix of emotions: relief, longing, anguish, love.   

“We are a family,” he said gently. “I’m still here for you.” 

Tin Men, Scarecrows, and Cowardly Lions

I was devastated when my ex left me. Though we’d never fought much in our marriage, the end had been bitter. We’d been growing apart for years. He’d focused on his daughters from his first marriage, as well as on his music career. I’d gotten caught up in my writing, political work, and book promotions. I had little patience for his fascination with the occult and with what I perceived to be conspiracy theories. I’d even gone so far as to diagnose him—a low blow for the spouse of a therapist. Some days I decided he had post-traumatic stress disorder. Other days, I was sure he suffered from generalized anxiety disorder. When things were really tough, I concluded he had bipolar II with psychotic features. Nevertheless, he agreed at first to couples therapy to try to fix our relationship. But when I discovered  that he’d strayed into the arms of another woman, I knew our marriage was beyond repair. 

After we divorced, I wanted to find the person I was meant to be with next. As a woman in my mid-50s, I was eager to prove I was still desirable. After two decades of married life, I had no idea what kinds of potential partners I might meet. As I began dating men online as well as IRL, I noticed—movie lover that I was—how elements of The Wizard of Oz provided a useful framework for grouping my experiences. Mostly, I found myself dating Tin Men, Scarecrows, and Cowardly Lions.

The Tin Men were interested in sex, but not emotional intimacy. They were disconnected from their hearts. Sam was a prime example of a Tin Man. He was several years older than me, and I found myself falling for him. He’d invite me over on Saturday nights and we’d cook creative vegetarian dinners. Snuggling in front of his fireplace would lead to passionate sex. Afterward, he’d yawn, sigh, and say, “You’re welcome to stay over, but I have a handyman coming at 8 tomorrow morning.” I’d leave soon afterward, feeling confused and lonely. 

The Scarecrows were ignorant of current events, including COVID protocols. Jack, a yogi a few years younger than I with a boyish physique, fell into this category. He appreciated my writing, which gave me an ego boost. I’d been suffering from insomnia since my divorce and his ready supply of weed, CBD, and CBN gummies were welcome sleep aids. 

“I don’t get it,” I said glumly once, while we were walking through a park near my home. “How come people aren’t taking Fauci’s messages seriously? It doesn’t make any sense.”

“You really think masks make a difference?” he asked, adjusting the bandana he wore on his face in lieu of a mask.

“Yes,” I said. “Don’t you watch the news?”

“Not really,” he said. “Honestly, I’d rather do yoga.”

The Cowardly Lions were traumatized by unresolved childhood wounds or painful past relationships. They feared they’d never find “the one”—that special partner who’d make them feel whole again. They tried hard, needed constant validation, and wanted me to do double-duty as a lover and therapist. Pat—a well-meaning IT guy around my age —was a Cowardly Lion. Although I admired him for the work he’d been doing on himself after his divorce, I didn’t like it when he made a habit of calling me immediately after therapy sessions.

“Today Carol held me while I sobbed about my mother. It felt so good. She wondered if I’m too dependent in my relationships and recommended some books on attachment. Could I borrow some of yours? Maybe we could talk about it when we have dinner together this weekend.”

Even as I dated other men, and explored my needs, desires, and boundaries in these relationships, I missed my ex. I couldn’t help wondering if there was something wrong with me. Was I more codependent than I thought? Was this a sign of complicated grief? Or was I just lonely?

In Search of Authentic Connection

Decades ago, I’d learned about the power of psychedelics in healing from Stanislav Grof, and with the resurgence of evidence-based research in this area, I enrolled in a certificate program at my former graduate school and found a local clinic where I could get hands-on experience guiding patients. They offered me a few sessions of my own to get a taste of what my clients might experience.

During one of the psychedelic journeys I took, I recalled the deep love I’d felt for my ex when we’d first met. I empathized with him for the pain he’d carried from childhood traumas, which sometimes flooded him emotionally and played a part in the ways he acted out with me and others. During another journey, I saw spermatozoa implanting eggs in colorful, organic, plantlike shadows on the wall, which in my mind represented how our daughter was the perfect manifestation of both of us–the miraculous result of our union. These guided journeys helped me work through my grief and rage toward my ex and connect with the possibility of forgiving him. I was also able to confront my existential loneliness and receive the message that we’re never truly alone, bound as we are in an interconnected network with ancestors, spirit guides, and all living beings. 

My breakthrough came when I finally admitted to myself how much I missed him. After two decades together, not a day passed that I didn’t see or hear something that reminded me of him. An Elvis song on the radio conjured up memories of the two of us at a party we’d attended early in our relationship at the home of one of his close musician friends. He’d sat in with the band, dedicated a song to me, and begun singing “I can’t help falling in love with you.” When the new season of Shtisel came out on Netflix, I longed to watch it together. When famous comedians died, I recalled his impressions of them and laughed out loud. I wanted to connect with him beyond our old labels of “husband” and “wife,” focusing on loving moment-to-moment and staying present in my body.  For months, he’d been sending me drawings he’d made and songs he’d recorded, and I began returning his texts. I read an article about how after so many years together, your nervous system literally regulates to your partner’s. No wonder that with him gone, I felt like a limb was missing. 

“Don’t get back together with him,” a handful of friends warned me.

My therapist was skeptical as well, at first, reminding me of my frustrations with him and of how misattuned he’d been to my needs toward the end of our marriage. But she also recalled how much I’d loved him and how safe his physical presence had made me feel.

Giving Us Another Chance

After the post-Encanto call, we began talking regularly, in increasingly greater depth. I was dating someone else at the time, but not falling in love. My ex told me the details of his failed relationship with his former girlfriend. He claimed he’d never truly loved her. I found it telling that he’d broken up with her right after we got together for a conciliatory lunch. 

“I know I screwed up with you,” he told me. “I did a lot of soul searching during COVID and went back to therapy. I know you have no reason to trust me, but I want to win back your trust. Even if you just want to be friends, I’ll accept that. I’ll be your best friend for the rest of our lives.”

He brought me flowers. He reached out regularly, came over and took initiative to sweep and mop my floors, fix loose handles and broken appliances, and help me tend to my garden. Whereas he’d been MIA during our daughter’s first year of college, he now voluntarily moved her in and out of her dorm room at the end of one term and the beginning of the next. He was financially generous in ways he hadn’t been in the past. 

He was also vulnerable. He admitted to past mistakes and cried openly. In his dramatic way that I likened to magical realism Latino authors, he told me he’d never stopped loving me, and that he’d give me all the blood from his body, should I need it. When I went on a ski trip with the man I was dating at the time, my ex bought me waterproof pants, a scarf, kindling, and matches to make a fire in case my boyfriend and I got stranded. When I saw these offerings in my satchel, my heart melted.

Could I reconcile with him after years of drifting apart? I’d spent so much time journaling, crying, processing, and learning to live on my own. Our old life had been ripped apart–like the wedding contract he’d torn up in a fit of anger the day he moved out. How would we heal as a family in a way that worked for us all?

I didn’t have the answers to these questions. But I also knew what we’d been through had humbled me, opened my heart, and taught me to stand on my own. I had more clarity about what I valued most in a relationship. Dating different men had helped me learn to communicate better. What if I practiced these newly acquired skills with a man I’d already loved for so many years—and still loved to this day?

No Place Like Home

My ex and I are in a new relationship, together. We started slowly. On our first date, we went to see an immersive Picasso exhibit, sat on a blanket in Golden Gate Park, and sipped wine as he stroked my hair. He suggested that we do some “cuddle therapy,” which sounded wonderful to me.

“I’ve realized I do better in a relationship when I have my own space,” I’ve told him. “I don’t want to move back in together. I want to love you because I choose to, not out of obligation.” I’d heard couples therapist Esther Perel talk about eroticism and how fire needs air, and this idea has resonated with me. Some space between partners keeps attraction alive.

“I understand,” he’s responded. “I don’t want to own you. You’re living your life. I want to be with you but only when you truly want me there.”

We’ve been doing more of the things we enjoyed when we first met. We paint together in his artist’s loft. We go out dancing. We hike and swim. We sing duets. We enjoy family outings again with our daughter. We explore sexual fantasies we never allowed ourselves to act on when we were married, distracted and busy as we were with work and parenting.

Even though the novelty of our current relationship is invigorating, my ex still gets under my skin at times. His very big personality sometimes feels overwhelming, as I am more introverted and quieter than he is. I don’t always agree with his spiritual beliefs or political views. We’ll always have to deal with our cross-cultural differences. Being together without a legal structure, and prioritizing our connection over predictable routines, requires patience, mindfulness, commitment, and open communication. We need to keep working on ourselves and looking at our part in what went wrong the first time around. 

But none of this changes the fact that my ex feels like home—and there’s no place like home. Loving means knowing, accepting, and embracing each other with our faults. It’s being with someone who knew and loved friends and family members we’ve each lost. It’s holding one another’s narratives—in our case, from the past twenty-five years. It’s being able to finish each other’s sentences or laugh prematurely at a joke you know the other person is about to make from the context you’re in, such as impersonating the meditation teacher who pronounced focus with a short o. It’s being with someone who loves the person you love most in the world—your daughter—as much as you do. Ultimately, love isn’t really a choice. It just is.  


Alissa Hirshfeld, MFT, is a marriage and family therapist and a spiritual director practicing in Santa Rosa, CA. She works in a ketamine clinic and has been certified to offer psychedelic-assisted therapy to clients. She’s the author of This Whole Wide World Is Just a Narrow Bridge and Living Waters: From Harvard Halls to Sacred Falls and a coeditor of Fury: Women’s Lived Experiences During the Trump Era. Contact: