I am a man flipper. I meet a man, fix him up and flip him to someone else. Unlike people who flip real estate — buying houses, renovating them and selling them for a tidy profit — I see no gain from this arrangement, only loss.
I don’t want to be doing this, but something attracts me to men who are emotionally withdrawn, and I have a talent for drawing them out. For their future wives and girlfriends, apparently.
I once saw a meme about the “dating pool” in midlife that featured an empty swimming pool with lawn chairs and debris blown into it. I laughed because it was so true. I never expected to be dating again in my 40s. I thought I had avoided this fate when I married in my 20s.
My first love was a heavy-drinking academic who quit drinking after we broke up and settled down with a wife and a baby on an acre in the Pacific Northwest. My second love was an emotionally stunted biologist who drove a Toyota Tacoma and listened to Kid Rock but within whom I recognized, and nurtured, a deep tenderness. He broke up with me the day after he finally told me that he loved me (I guess it scared him), and he later married the woman I had lived with when I was dating him.
After those two heartbreaks, my friends joked that my secret talent was teaching men how to love someone — just not me. I thought I had broken the pattern when I married, but the man who became my husband turned out to be mercurial and cruel. We had a child together, but as hard as I tried, I was never able to fix him. At least not for me.
After our divorce, he married a woman a decade my junior, and I wondered if all the work I had done making him own up to his behavior and understand the need to change would mean that his new wife would be spared the mistreatment I received. I wished a calmer marriage for her, which they appear to have achieved.
Years passed, and in my post-married life, the men flipping resumed. There was the former monk who abstained from everything, including sex, but when I stopped seeing him, he moved into a comfortable relationship with an acupuncturist. Then the wildland firefighter who chased me for years and disappeared when I was finally available. All of those setbacks had turned me into a woman who was disillusioned, celibate and ready to give up.
Then, at 40, I met Rich. He was sitting across a bar and looked like he was 25 (he turned out to be 32). Tall and skinny with kind eyes, he felt safe to me, like someone I would never really fall for — not in the way where I lost control.
I invited him over, had sex with him, told him that we should do it again sometime and entered his number into my phone. I knew it was risky, but he was so sweet and earnest. That safe feeling wasn’t something I was used to.
Because I’m a divorced mother and protective of my son, I only let Rich visit when my boy was at his father’s house, so we saw each other every other weekend. It was intensely casual but also weirdly stable. These weren’t booty calls; they were planned visits. I cooked us dinner, and we cuddled.
We liked each other, but our dynamic was that I took care of him. I knew that for a relationship to be serious, I needed someone who took care of me too. Still, I enjoyed our time together and wanted it to last.
As we grew to know each other, I learned that he was old-fashioned in matters of the heart. The youngest of seven children, he was the family baby. He was strictly monogamous, and I never worried that he was seeing anyone else because he was honest — almost to a fault in how he routinely expressed his hesitations and doubts.
He also didn’t try to charm, flatter or otherwise tell me what I wanted to hear, which was both disarming and strangely nice. My marriage had made it hard for me to trust men, but I trusted Rich.
The first time that we almost broke up was when he came over and said, “I feel like we should break up. I just have a feeling that this is going to end terribly.”
I looked at him for a long time, then said, “But what if it doesn’t?”
Someone asked me once where I thought my resilience came from. I hesitated, then said, “For women, too often, I think what we mistake as resilience is actually just endurance.”
I don’t know if my endurance has served me well. It takes a special kind of endurance to look at the train barreling down the tracks and say, “But what if it doesn’t hit me this time?”
Rich and I had more breakups after that. I started to want more, but our lives were incompatible, so we broke up and remained friends. Then I accepted a job 70 miles away, so it seemed OK for us to have sex “just one more time” before I moved, but then I wasn’t moving that far away, so it seemed OK if he came to visit occasionally.
Then the visits were so nice that they became regular, then we spent four days together while my son was at his father’s over Thanksgiving break, and during that visit, when I had the beginnings of a cold, Rich walked my dog for me, brought me tea and cooked for me.
Suddenly, I sat at my kitchen table while he made cornbread and thought, “Oh, no. He’s taking care of me now. This is dangerous territory.”
And what does it say about me that when a relationship starts to get good is when the dread creeps in? What does it say about my history of heartbreak that I assume men will leave me when they finally learn how to love me? In horror movies, things are always calmest just before the monster springs from the closet. I have spent most of my adult life anticipating monsters.
And they arrived. In January last year, just before the pandemic, he had a crisis of faith and broke up with me. This time, it lasted. Neither of us entered this relationship thinking it would be forever, but still I was devastated.
There is a peculiar kind of bittersweetness to living with a broken heart in winter, even more so while socially distancing alone with my son. I kept expecting to wake up and not miss Rich, but each morning was a disappointment.
It turned out that he missed me too, so in July, while my son was at his father’s place for a long summer stretch, we got back together, and we were honest with each other — that we didn’t know where our lives were going, but we could be committed to each other while holding space for that unknowing.
I have never existed well in a space of uncertainty, but my divorce taught me that there are no guarantees in relationships. Maybe, I thought, just this once, the train would jump the tracks before impact. But if it didn’t, I knew I would have the endurance to survive it.
In the eight months that we have been back together, we have finally said “I love you,” and he has met my son (they like each other). We have also talked about making a home together. I send him listings from Zillow, and he offers commentary. I know that neither of us has ever loved another in this way, and that what we have is special.
Still, he has told me that he thinks he wants to have children someday, and more children are not in my future. The monsters loom. I have to live with this unknowing. My endurance keeps me here: Watching the train and hoping that it will jump the tracks. He told me the other day, “You’ve helped me grow so much. I’m a different person than I was when I met you.”
I know it’s true, and when I look at him, I can see his future with someone very lucky, which is why I don’t want to flip this one just yet. Maybe, this time, that very lucky person will be me.
Kelly Sundberg, who teaches writing at Ashland University in Ohio, is the author of the memoir “Goodbye, Sweet Girl.”
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