When Your Big ‘Midlife Divorce’ Isn’t Your First
Unlike most things in life, divorce does not necessarily get easier with practice. Whether a separation goes smoothly or not depends more on the particulars, like how long a couple was together and during which phase of life. For Adam, his first divorce in his mid-20s felt simple compared to the one he’s going through now in his 50s. “I think the only debate was an old bill over a cable box that never got returned,” he told me. “Now we have children, cars, houses, and retirement assets.” The midlife divorce can also carry more emotional baggage. Couples have sunk more time into therapy and feel more hopeless about their future dating prospects. One woman in her 50s told me that after her first separation, she felt she still had “my whole life ahead of me. Now I just feel like I’m old Raggedy Ann,” she said. “I can’t even imagine taking my clothes off in front of somebody.” But others said their first divorces felt like a gut punch, while their midlife separations were merely the unsurprising capstones to years of unhappiness. “It was my first big mistake,” Debra said of her first divorce, at 27. “Everything I did up until that point was gold-star shiny.” She describes her second marriage, which lasted more than two decades, as something that “petered out.” “I looked at my life like a pie: one-quarter was my son, one-quarter was work, one-quarter was my friends, and one-quarter was my husband,” she says. “And I thought, You know, three out of four ain’t bad.” Below, four people on what they did (and didn’t) learn from going through the divorce process twice.
“My first divorce was simple in the sense that I knew I didn’t want to stay. My second felt like more of a failure.”
—Alice, 52, Washington
My husband and I met at college in Malaysia when I was 16. We transferred to schools in America, and by 19, we were living in California and I was pregnant. It was definitely not planned. I was in denial up until the point that I went into labor. My Christian parents supported me financially, but they did not approve of this boy because he was Muslim. They cut me off. His family insisted we get married right away. I didn’t want to because he was emotionally abusive and isolated me from my friends. But I had to keep a roof over my head. My mother-in-law brought an imam from the local mosque to our apartment who performed the ceremony. I was still in school, so my mother-in-law said she would take the baby to Malaysia and come visit us every six months. I was overwhelmed and had no idea what I was doing, so I agreed. I graduated, started working, and told him I wanted a divorce. He didn’t take that well. The day I moved out, he begged me to stay. Then he shoved me up against a wall.
At first, the paperwork to get our divorce was pretty straightforward and my husband accepted the situation. But every time his mom came to America with my daughter, she refused to let me see her; my ex would sneak me visits. I met my second husband a year after my divorce. He was working at a dating service, and I went in as a potential client. I thought he was cute, so I asked him out. At first he seemed to be different, but I wasn’t on my guard. His mom was deceased, and I was just happy not to have another overbearing mother-in-law. I see now that there were a lot of similarities between him and my ex. When we started dating, we were going away on a weekend trip. I saw the sign on the freeway and said, “Hey, shouldn’t we be going that way?” And he just lost it. He said, “Don’t tell me what to do. I’m not stupid.” I just thought it was a onetime thing and not a big deal.
He met my daughter a few times and seemed to genuinely care for her. The next time her grandparents were in the country, I decided that I would file for full custody of my daughter. My ex’s family helped him lawyer up, but I couldn’t afford one on my own. I was making $5 an hour out of school. My employer at the time ended up fronting me some money so I could pay the $3,000 retainer. The judge ended up giving us joint custody. On another visit, a few months later, her grandmother asked the judge if she could take the baby back to Malaysia for two weeks for Ramadan. I had a sinking feeling in my stomach that she was not going to bring my daughter back. And that’s what happened. When I called my ex, he said, “You know my mom; I can’t do anything.” I filed a report with the police and the FBI. But Malaysia didn’t have an extradition treaty with the U.S. then, so nothing happened. I didn’t have a lot of financial resources, so I continued on with life and kind of put my daughter out of my mind. I didn’t talk about her; a lot of people didn’t even know I had a daughter. My new boyfriend was supportive and would claim he could go to Malaysia to get her back, which I obviously wasn’t going to let him do.
I look back on that situation with so much guilt that I didn’t do enough to get my daughter back. I was 24 and became determined never to put myself in a situation where I had to depend on someone financially. I vowed to always have my own source of income so I could feed myself and put a roof over my head.
For the most part, I was happy in the relationship. He was funny, smart, and a good cook. We had a small wedding with around 15 people outside of Yosemite that cost about $3,500. A year later, we had a son. My husband didn’t have much money, and he offered to sign a prenup. I was really in love with him, and I guess I wanted to prove that it didn’t matter to me. But I started to notice that he’d make fun of my friends. If I wanted to hang out with them after work, he’d get so pissy and jealous about it. When the baby cried, my husband would say, “Can you just get him to shut up?” When our son was 3, I found out he was having an affair with someone he met online. I forgave him because I thought we could still make it work and I wanted to stay together for our son. But I started to emotionally check out of the marriage. I went from being in love with him, to being hurt by him, to feeling apathetic.
When I found out he was having another affair when our son was 5, I didn’t care. I had made a plan to stay with him until my son was done with high school. I was overprotective of my son because of what had happened with my firstborn. I didn’t want to risk losing another child through a divorce. I retreated and didn’t speak much unless I was interacting with our son. Four years later, I found my daughter on Facebook. She was 16 and still living in Malaysia. Our first contact on the phone was just a lot of crying. We kept saying, “Oh my God, it’s you!” I flew there to see her with my mother, who lived in L.A. at the time. My mother-in-law hired a couple of bodyguards to follow us around. My husband was supportive — it was the only time in our marriage that I was able to take a trip by myself.
After that, it was like a dam broke emotionally. I’d be sitting in yoga class, start bawling, and be so embarrassed that I’d have to leave. A few years later, I decided I couldn’t wait any longer to leave the marriage. I became very depressed, and when I came home from work, I only had energy to watch TV. I stopped taking my son, who was 12, out on the weekends. He said, “Mom, what’s going on? Why are you just sitting there?” That helped me snap out of it and realize how bad things were. I switched careers and got into real-estate investing. I started meeting people, and that spark for life came back. I tried to get my husband involved, but he thought my job was a scam and made fun of the people I was hanging out with.
The first time I told him I wanted a divorce, he threatened to kill himself. He walked out of the house. I panicked and called the cops. When they found him, he claimed it was all a big misunderstanding. He begged me to stay and we went to counseling for a year, but things were already too far gone for me. The second time I brought up divorce, the same thing happened. The cops brought him to the hospital, and he called me to say, “You can’t leave me. I just found out I have colon cancer.” I told him I was sorry, but I was going ahead with it. I was afraid he would get violent, so my son and I stayed with a friend. I came home a week later, and he said he’d agree to a divorce. He told my son, “I got cancer and your mom is leaving me.” My husband moved out, and I let him take everything except for the couch. He tried to come after my 401(k), so I hired a lawyer who helped us split the assets. I didn’t like spending the $7,000 on legal fees, but I didn’t want a repeat of my first divorce, where it felt like I had no control. My ex would be kind of nitpicky about splitting expenses for our son or send me a nasty email, and my lawyer would always handle it.
My son was very angry with me for a year and a half. He would tell me I was tearing the family apart and not living up to my marriage vows. What he said sounded like his dad’s words. My ex was also lying about me on Facebook, about how I was a gold digger now dating a millionaire. That wasn’t true; I wasn’t dating anyone. We had joint custody, and at our weekly parent exchange, he would park outside the house and refuse to say hello. I told all my girlfriends, “If I ever talk about marriage again, you need to slap me.” I was 40 and felt like, I’m too old for this shit.
I wasn’t ready to get married the first or the second time. I didn’t fully know myself yet and I allowed these men to control me. I was too much of a people pleaser. My first divorce was simple in the sense that I knew I didn’t want to stay. My second felt like more of a failure because I had wanted to get married, I was in love with him, and we put in all those years. I thought, Oh great, I failed again. I met my now husband in 2023. I wanted a committed relationship, but he wanted to get married. We didn’t get a prenup because, at the time, he had more money than me. I’m not worried about divorce, though. It’s a much better relationship than my previous husbands. He sold his business and moved across the country to be with me.
“The emotions of divorce don’t get easier, but the wisdom and clarity you gain makes it easier to navigate.”
—Tracy, 47, Montana
We met at a manufacturing plant. We both studied engineering — I was doing an internship and he had a full-time job. It was totally a karmic connection and love at first sight. We got married a week after I graduated, when I was 23. It was a small-town Midwest wedding at the community center. I had eight bridesmaids, and between 300 and 400 people attended.
We moved to New York, where he had a job offer with JPMorgan and I got an offer with a big consulting company. It was 2001 and we were living in a shoe box on the Upper East Side. I loved him, but I couldn’t figure out why I wasn’t attracted to him. He would say “groovy” and bought thrift-store button-down shirts from the ’70s. He had these black horn-rimmed Buddy Holly sunglasses. My mom would always say, “Just keep working on it.” We went to counseling and bought a condo on 62nd Street, but I just couldn’t tell my heart to feel that way.
I remember driving to the airport on a work trip and driving off the edge of the road. For a split second, I thought, Maybe it would be easier if I just died. In that moment, I knew. This is not okay. I am not happy. That night, I talked to my best friend who had given a speech at my wedding, and she was the first person to tell me it would be okay if I got a divorce. I had an affair with someone from work shortly after that. I think subconsciously I was probably like: All I have to do is have sex with someone and he’ll finally give up on me. But he still wanted to make it work. At first, I couldn’t hold my ground, but a few weeks later, I said, “I want a divorce.” It took a while to sell the condo, so we took turns couch surfing at our friends’ places. There wasn’t much to split up — we each took a futon. Everything was pretty amicable. I realized that I deeply desired a masculine man.
A few months later, I met my second husband, on July 4. He was a mountain man who had a snow-removal business in Montana. I had plans to go out there for a wedding, and I spent about two and a half weeks with him. We had a whirlwind romance. I got home a week later and realized I was pregnant. We were both thrilled. I moved into his house, and I put pressure on him to get married. I loved him and I wanted us to be a family. Things weren’t perfect, but I sort of just chalked it up to us being new parents. I just thought I could make it work. It’s almost like the tables were reversed from my first marriage. Now I was the one willing to do whatever it took to make things work. We had a wedding in 2015 when our daughter was 18 months old. It took place on some land in the mountains, with a reception at a local barbecue joint; about 100 people were invited. That did not fix the relationship. I soon realized that he was very emotionally unavailable. I told him I needed words of affirmation, but it didn’t work. We started counseling, and in one of our sessions, he looked at me and said, “Okay, Laura, I think I know what you’re saying you want out of a husband. I don’t know if I can be that person, and, honestly, I’m so busy I don’t even know when I can try.”
By now our daughter was 2 and a half, and I started to imagine the type of woman I would become if I continued to stay in the marriage. I’m typically full of energy. Around him, I had to shrink. I just had visions of turning into a horribly unhappy alcoholic. I came home one night, looked at him, and said, “This isn’t going to work.” I think he knew it too. The first words out of his mouth were, “I just don’t want you to leave Montana.”
My first husband didn’t want a divorce, but my second husband was like, This is the right thing to do. If she stays here and my daughter stays here, I’m getting everything I want. The logistics were more complex than the first, but he made things as easy as possible. We were able to work through the custody pretty quickly, and I wanted it to be 50-50. He kept the ten acres of country land we had bought, and he helped me build my house on some property in town. We co-parented together for six years, and it went so well that, in 2022, we tried getting back together. Our friends were thrilled. But he was so terrified of emotional intimacy that he would gaslight me by saying, “Why are you so complicated?” and “Why do you have so many needs?” I quickly realized again that it wasn’t working. When I told him, “I can’t keep going on like this. The distance between us is impossible,” he basically said that I was 100 percent of the problem. I waited for him to finish talking, looked at him, and said, “I need to call it. We can’t be together anymore.”
For the last 12 years, I had bent my life around what he needed. I gave up proximity to my family — my daughter has eight cousins in North Dakota and is really close with her grandmother. So for this separation, I voiced my opinion in terms of what I wanted and what I thought was best for our daughter. I was priced out of our town, so I moved an hour away. Now he can’t just pick his daughter up from school on a whim, but she’s close to her dance lessons and I can see her school from my office window. The emotions of divorce don’t get easier, but the wisdom and clarity you gain makes it easier to navigate. I’ll be much more mindful of giving myself to anyone in the future. For the first time, I don’t really have an interest in dating or having a man in my life. Women will say things like, Should I go on a date or stay home, wash my hair, cuddle up with my cat, and watch Netflix? I’ll take the latter, please.
“Both divorces taught me to be better about speaking up. I’m a people pleaser and always have a fear of making someone else upset.”
—Debra, 57, New York
I met my first husband at summer camp when I was 19. We both went to the University of Florida and moved to New York so he could do a Ph.D. in psychology. I liked his look: dark hair, dark eyes, Jewish. He wasn’t crazy tall, which was important, because I’m barely five feet. We moved in together and got engaged. There was a little bump when my parents were planning the engagement party and he got cold feet. We just took the pressure off of having the party and stayed together. We had a typical country-club wedding in South Florida with 150 people. My parents paid for it, but it wasn’t over the top. I was definitely happy. I felt secure. He became part of the family. But less than a year later, he looked at me and said, “I don’t know if I want to be married anymore.” This felt different from his engagement jitters. From that point on, we were living in limbo and just playing the roles of being in a couple. As our anniversary approached, he said he was going to stay with his cousin. At that point, I told him we needed to go for counseling. We went to a session, and I was surprised by how much I had to say. I’m a Pisces and usually go with the flow.
One day I was feeling really low and called him hoping for a little token of reassurance. He told me that he didn’t want to go back to therapy. I said, “Say what you mean. Don’t be wimpy.” He finally said, “I want to end the marriage.” I said, “You’ll hear from my lawyer” and hung up. Maybe that was a line from something I’d heard on TV. Then I went and saw my girlfriends. I packed up all his garbage and put it in the building’s storage room with a note that read: “Your stuff is waiting for you.” When he called during a family tragedy, I told him, “You’re no longer part of this family.” The person he knew had always made things easy. It felt empowering to take back some control, because he had always been in charge. But it also felt like a loss of innocence. It was my first mistake in life. Everything up until that point had been a gold shiny star.
It was a very easy divorce because we didn’t have that much together, maybe some bank accounts and investments. We were renting an apartment. I think the total legal bill was around $1,200. I put the emotional part aside and focused on work, which I’ve found out is my M.O. I went to Club Med with my girlfriends and dove back into the dating world. I started seeing a very close friend who was in our wedding party. We were raised with the same middle-class values and had a lot in common. My ex was the kind of guy who left the house at 11 p.m., but my new boyfriend liked to stay in and watch T.V. I was still living in the same apartment, now by myself, when I started having insomnia and panic attacks. All those feelings about the divorce I had repressed were coming back up months later. There were a couple of times when I would call my boyfriend really late at night and he never picked up. Once, I was melting down over whether or not I should move back to Florida, and all he said was, “I’m not coming.” Those should have been red flags.
I went to therapy, started taking medication, and got myself together. My boyfriend and I moved in together and got married in 1996. It was more of a party. I wore a cocktail dress. This time, we paid for the wedding, and it was around $12,000. A few years later, I had my son. I noticed my husband becoming more reclusive. In the beginning, he had friends and would go out for dinner, but that happened less and less. He just became less happy and never really wanted to go anywhere.
He worked in his family plumbing business, and when our son was in kindergarten, it shut down. His father wanted to retire, and my husband didn’t want to take over. I was so excited for him because he played in bands and he could finally pursue some form of creativity. Instead, he fell apart and had big mood swings. He went to therapy, started taking medication, and eventually got another job doing plumbing and construction. But sometimes he couldn’t handle the pressure. One time, he had a panic attack at work and had to go to the ER. At home it was kind of the same thing. Sometimes he was the good version of himself. Many times he was withdrawn and there was no intimacy between us. I can remember crying about how he didn’t want to be sexual with me, because I knew it wasn’t normal. It didn’t change, so I just got to the point of apathy.
I was a working mom trying to be everything to everyone. When I got home, I just wanted to go to bed. I looked at my life like a pie: one-quarter was my son, one-quarter was work, one-quarter was my friends, and one-quarter was my husband. And I thought, You know, three out of four ain’t bad. I lived like that for a very long time. I didn’t mind if he didn’t want to see my family. It was easier when I didn’t have to deal with the weight of his moods. After seven years at his job, he was fired, and he talked about pursuing big ideas, like writing scripts. This time, I had no faith in him. I could see he was all talk. He loved nothing better than to talk about himself and not change.
At a certain point, it seemed like he was just choosing to be miserable. He was like a fuse that could go off at any point. If he had to wait to make a right turn because there was traffic, he’d be pissed off. I was very sensitive to his anger because of my son. How much of a happy face could I always put on?
It was our 16th anniversary, and I remember not being able to find one card at the store that resonated. I wasn’t feeling any love or warmth toward him. A few months later, on New Year’s Eve in 2013, he kissed me on the mouth at midnight. I was grossed out and immediately turned my head.
He was smoking a lot of pot and spending a lot of time on Facebook. One day, I read his messages and found out that he was having some kind of an emotional affair with a woman he had met at his high-school reunion, which I had encouraged him to go to. He immediately said, “I’m going to end it.” And I said to him, “You don’t have to.” I didn’t care. At that point, he started sleeping in the back room. I reached out to a lawyer, who confirmed that since my husband wasn’t employed, I could be on the hook for alimony. It would be better to wait until he had work to go ahead with a divorce. A few weeks before he started a new job, I looked at a cell-phone bill and saw that he had spent a whole weekend calling this woman. At that point, I told him I found a mediator.
He just went along with it. He never once tried to fight for anything. We spent 2014 in a lot of mediation appointments, which cost around $5,000. My lawyer was $18,000. I wasn’t looking to screw him. I was staying in the house, but I agreed that at the point of sale, it would be a 50-50 split. At first, I wanted a legal separation — an agreement to divide up our assets that would allow me to stay on his insurance since I was self-employed and needed the benefits. I was the breadwinner for our whole marriage, so I thought now he can keep me on his plan until our son goes to college.
Before anything was set, this woman he had been seeing broke up with him. He was a mess. He came to me in the wee hours of the morning, and I talked to him like a friend. He said, “I can’t believe how understanding you are,” and inside my head, I’m thinking, I don’t want anything to delay getting him out of the house. A few months later, the legal separation was through and he moved out.
He’s a good dad. He never missed a child-support payment. He’s honorable, and all that good stuff I know about him too. We finally got divorced in 2023. It was just paperwork at that point — he had already taken whatever it was he was taking. I was in such a different space than I was in my first divorce. I was an adult. I had savings. I owned a house. I had a grown child now. I was confident that it was the right choice. Unlike the first divorce, it was my choice. He was ten years older than me, and I just thought, I don’t want to wipe his butt. But I experienced a lot of loss in terms of his extended family, which I didn’t deal with the first time around. I would call my mother-in-law as often as I would call my own mother. I used to talk with his sister once or twice a day. He had all these nieces and nephews, and I just loved being part of that big family.
Both divorces taught me to be better about speaking up. I’m a people pleaser and always have a fear of making someone else upset. I sacrificed a lot in my last marriage — there were many social situations I turned down because I knew he wouldn’t want to go. I still fall into this habit, but I’ve been with my partner now for seven years, and I’m always trying to improve on that. I’ll tell him when I don’t have the energy to see his family. He’s not talking about marriage, and I’m not looking to do it a third time. That would put me in a panic. I’ve already been divorced two times, and that wasn’t part of the plan.
“Unlike in my first divorce, our decisions impact other lives.”
—Adam, 51, Colorado
We met in college in the mid-’90s. Those years are a little blurry. I didn’t realize she had a drinking problem at the time because I was a 20-year-old idiot and everyone was drinking too much. Our relationship had a major emphasis on convenience, and we had a good physical connection. Five years later, we had a small wedding with immediate family in a hotel downtown. It cost maybe $5,000 and our families paid. After that, her drinking became more of an issue. One time, officers from the Denver Police Department were banging on my door at 2 a.m. because they had found her wandering around in the cold with a bloodied head and very little in the way of clothing. While I was sleeping, she had hit her head on the tile wall and then ran out into the chilly February evening in her running shorts and tank top. Other times, she just never came home. She also had an affair. There was a lot of friction in our relationship, and I would call her out on her shitty behavior. Within a year, she said, “I’m moving out. I want a divorce.”
It wasn’t a surprise because our relationship was really emotionally difficult. It was heartbreaking because I loved her, but it wasn’t financially or logistically complex. We were renting a place and had no real assets. We drove a couple of junky cars that had been paid off.
I moved into a complex of condos and lived across the courtyard from a woman I started dating. There was a physical attraction and we had a lot in common, like the fact that we have divorced parents and are Jewish. Within a few years, we bought a house and got married at a private dinner club with 200 guests. It was in the neighborhood of $50,000 and was everything you would picture an awful, overpriced wedding to be. Our first son was born a year later. The next ten years were amazing. She was doing administrative work for the Department of Energy outside of Denver, and when our oldest was born, she left her job and didn’t go back. I started a real-estate finance company, and after years of trying to conceive, she got pregnant again in 2014. As the kids grew older, she spent a lot of time at their school volunteering, which eventually developed into a full-time job. She ended up getting a master’s degree in education and is now a teacher.
By 2018, her aging mother and stepfather were not in good shape. Her mother also had Alzheimer’s and had to be on a lot of pain medication. The cost of putting them in retirement facilities was really significant, so we decided to move into a home that could accommodate all of us. I warned my wife that this was going to eventually be very traumatic and that she needed to prepare for the fact that they were going to die there. But I think that was kind of in one ear, out the other. I enjoyed living with them, but it took an enormous toll on my wife. She had a complicated relationship with her stepdad, and her mother deteriorated to the point where we had to change her diapers. Her mom passed away in 2021, and I think this was the beginning of the end of our marriage. Her stepdad died a year later after falling and breaking some bones. We slowly started drifting apart. She began sleeping in the guest room and claimed it was because of my snoring. We had done counseling in the past, and I remember suggesting we go back. She said we couldn’t afford it, which I was surprised by. I thought, I’ll eat ramen if it means we can figure out a budget for this. A few years ago, on Valentine’s Day, I bought her custom jewelry from an Israeli artist, inscribed with our children’s names in Hebrew. Her reaction was very narcissistic: She accused me of giving her something thoughtful just to make her look bad because she hadn’t gotten me anything.
She had dropped a ton of weight, and I didn’t really think there was a problem until 2023, when I stumbled upon a bottle of Adderall and realized she was taking it. I didn’t ask her about it, because at that point we were so defensive with each other. The ability to have any kind of communication had gone out the window. But I did wonder about how the drugs were affecting her behavior and whether she was abusing them. I still don’t know.
I was trying to diet and exercise since she had expressed concern about us being older parents. My son made a comment about how I was making changes in an effort to salvage our relationship and his mother was not. He said it bothered him. I realized I didn’t want my children to be burdened by this. Last spring, I said I couldn’t do it anymore. She absolutely agreed. We both knew we were never going to get back to a good place.
We agreed we would do this without legal representation, which is how most affluent couples are able to get through it, but then earlier this year I received a court notice that she had hired an attorney. She believes there’s money that’s not being disclosed and that my parents are helping me hide it. There’s no money. I wouldn’t have lied on a sworn financial statement submitted to court. She made a fairly thoughtful split-custody schedule for our child who is still a minor, but we had agreed to certain things that she has not followed through on, like that she would take all of our pets. Instead, the three cats and one of the dogs is still with me. We agreed to a date when she was going to move her stuff out, and that didn’t happen.
She is certainly a very different person than when we met and married. There’s a lot of delusion and behavior that I want to blame on the drugs. I want to believe that’s not actually her. But in truth, I don’t know what’s going on. After my first relationship, I would have recognized and walked away from even the slightest hint of alcohol abuse. With that type of addiction, you can see the evidence and the results. When we’re talking about prescription drugs, I have no idea whether she has a problem or not. By the time I found out my wife was taking Adderall, our relationship was already over.
Now I’ve hired a lawyer as well, and it looks like whatever we had in the way of liquid assets will all be spent on legal fees. Compared to my first divorce, everything is more complex, like our co-parenting schedule and all the bank statements and tax returns that have to be assembled for the divorce to go through.
There are still moments when I think I would like to rectify things between us. Those are becoming few and far between. But unlike in my first divorce, our decisions impact other lives. I think about the long-term devastation. How will this impact my kids? What will my future relationships be? I worry about whether I’ll ever find someone compatible to be with again.