| Family First Feature |

Second Chance

Four key insights into building a successful second marriage — and insights from those who've done it

Tammy Weber* got married at 19. By the time she turned 21, they had two children, but no functional marriage.

“It took me time to leave. I had to be ready to make the move, to get divorced,” she says. Her children were still very young when her marriage ended, and she spent several years as a single mother before she married her second husband, who was also divorced with kids. “We were still pretty young. I was 25, and he was 29. We were a little seasoned, a little beaten, but also really ready to have, and were grateful for, a fresh start.”

A fresh start is wonderful, but if so much effort goes into making a marriage successful the first time round, what happens when it’s a second marriage and you’re also dealing with stepchildren, or custody arrangements, or moving into a home with preexisting memories and possessions, adult children with their own complicated emotional landscape, and a spouse who has experiences from a previous marriage? How do you navigate all those additional factors while developing a new relationship?

Sarah Rivkah Kohn, founder and director of Zisel’s Links and Shloime’s Club, organizations which support children who have lost a parent, has a unique perspective on the topic of second marriages. Over the years working with bereaved families, she noticed a disturbing trend: Many of the widows and widowers she was in contact with had gotten remarried, but these second marriages were frequently breaking up. Sarah Rivkah and her team undertook a mission to learn more about what makes a successful second marriage so they could help prevent this painful situation. They interviewed 60 men and women who’d lost their spouses and remarried, some successfully, others less so. The question they asked was: What do you wish you’d known before remarrying?

As the team conducted their interviews, they noticed a certain pattern emerging from the responses. Looking at the data, they identified four elements that exist in successful second marriages: a) couples marry for the right reasons, b) they have a financial prenuptial agreement, c) they have a mutually respected rav, and d) they attend regular therapy sessions long-term.

Marry for the Right Reasons 

“Never marry to solve a crisis,” cautions Sarah Rivkah. “The crisis could be that the kids are so challenging, or that it’s so hard to live alone, or that it’s not possible to manage financially.

“These are all realistic things that single parents face,” she empathizes. “But however counterintuitive it sounds, marrying someone when you can’t manage alone is a surefire way to get into an unhealthy relationship out of desperation. The home front needs to be settled, everything needs to be going well, and only then should you introduce a new element into your life in the form of a new spouse.”

Tammy recalls how after her divorce, even though she was still very young and had young children, she had such a good support system where she lived that she opted not to move back in with her parents, who lived in a different city. “I had a sister in town who I was very close to, and she was always a place I could bring my kids. My neighbors were amazing.” She knew moving back home wouldn’t be the ideal arrangement for her and that the key to her having a successful future was to build the best life for herself that she could.

A Financial Prenup Agreement

Financial disagreements are one of the top reasons for discord in a marriage, and in a second marriage, the financial details can be significantly more complex. Sarah Rivkah encourages people dating the second time around to ask uncomfortable questions like: Who pays for the child’s tuition? Who’s paying for the child’s wedding? Who’s paying for a bar mitzvah? Who’s in charge of utilities? Are we moving into your home? Are we selling mine?

“There must be a financial prenuptial agreement that answers all these questions,” she says.

She also points out that people who remarry at an older age should consider making a health proxy prenuptial. It’s extremely helpful to decide who’s in charge of health decisions. Is it going to be the person’s kids or their new spouse?

Esther Berger* married her second husband, a widower with 11 children, a couple of years after her first marriage ended in divorce. She herself had four children. Esther recalls that her husband went to a lawyer and made a prenup contract. “He made it a very positive thing in my favor, but I couldn’t bring myself to sign it. The idea of a prenuptial was too unpleasant. I was so starry-eyed, and I just couldn’t do it.”

Tammy remembers the period when she dated her second husband as an almost magical time. They had so much in common and were such a good fit, and she didn’t want to mar the experience by bringing up finances. She was receiving some support, however minimal, from her ex-in-laws, and was also working, but after her second marriage, the support from her former in-laws dwindled, and she and her husband found themselves in situations so complicated that they ended up going to a din Torah and to court.

Barbara Kleid got divorced after six years of marriage, and enjoyed 11 years with her second husband before his unexpected death. She is now married for the third time. She went into this marriage very prepared. “We were very up-front about financials. We have a prenuptial, of course. We have a shared bank account, but I also have a separate one. And I have certain bills I pay and certain things he does. You have to protect your children, on both sides. It’s not just what I do for my kids; it’s what he does for his kids.”

A Mutual Rav

Esther remarks that people have different criteria for a husband the second time around. “The first time around you’ll be looking for tall, dark, handsome, charismatic, all that stuff — which is nonsense. When you go through life and experience tzaros, you see that the only thing that matters is middos, and that comes in all kinds of packages.”

Because people tend to marry differently the second time than they did the first time around, with more intermixing between hashkafic or cultural “types,” it’s so important to have a rabbi that both spouses respect and can ask questions of. “There needs to be a rav compatible with the new family setup, someone who can also consider the needs and background of any children from the previous marriages,” says Sarah Rivkah.

Esther wholeheartedly agrees with this. “Things do come up, and you need to be able to talk to someone and ask. It’s really important to have a wise rav the two of you can call,  someone that’s savvy on second marriages, because I think that really makes a big difference. The fact that my husband had a rav to listen to, and his rav was a tzaddik and very wise, was so helpful.”

Benefit of Therapy

Therapy is also a beneficial avenue for working through complex feelings. Sarah Rivkah noted that all the respondents of the survey felt that when a couple is dating seriously and continuing into a new marriage, they should regularly see a therapist. Universally, they reached a stage where things were working (whether it was six months, one year, or three years into the relationship), they quit therapy, and then felt they’d left it too soon.

“As long as there are children from the previous relationships living at home, there will be complicated dynamics,” says Sarah Rivkah. “There are alliances that were previously built, and there are the curveballs kids tend to throw at couples. Continuing in therapy for as long as there are children living at home can be a very wise thing. Therapy sessions are a really good safe space to bring up things instead of allowing them to fester. Preferably, the therapist should not be one either spouse was seeing previously, as then there may be an issue of whom the therapist is aligned with.”

Managing Expectations 

In addition to the four elements of a successful marriage that Sarah Rivkah identified, there were a few additional universal experiences she noted.

“Whenever I hear someone say, ‘I never expected that…’ I know there’s a problem,” she says. “There are many permutations of this: I never expected his kids to be so difficult, they were so sweet when I met them; I never expected money to be so tight, he said he was okay; I never thought I’d have to move.”

Says Sarah Rivkah, “I can only tell you that when expectations aren’t spelled out, and in some cases, written out, before marriage, there’s a lot of room for trouble.”

She encourages people considering dating for remarriage to think about their expectations. How do you like your day to go? How do you like your home to run? “Don’t judge yourself for your expectations,” she says. “Instead, verbalize what they are. And if at any point during the dating process, what you envision makes the other person uncomfortable, and he feels he’s not up to it, then you’ve just gotten out of a situation that could have ended in divorce. You spared yourself.”

Barbara says that, “You have to expect the unexpected, and sometimes you have to let go of your expectations. Everybody, I think, has expectations, and when that doesn’t go your way, you have to come to terms with that.

Another thing to keep in mind, Barbara suggests, is to acknowledge what “My mother always said: you never know somebody until you live with him. That is completely true.” She shares that her husband has some personality quirks, as all people do, and shared how after the first Succos she was married, “I said something to my husband’s son about this particular quirk, and his son burst out laughing and said, ‘Oh, we’ve all been waiting for you to see this.’ ”

“When I first started dating after I got divorced, I remember thinking, I have to broaden my horizons,” shares Tammy. She set certain parameters for what she’d be open to, and decided she’d be okay with anyone up to ten years older than herself, and someone who had a different levush than she was used to. In the end, she didn’t have to compromise on any of the external or hashkafic things she’d considered; her challenges came from their ex-spouses.

Stepchildren and Former In-Laws

“Sometimes I hear people say, ‘the kids broke it up,’ ” says Sarah Rivkah. “But research doesn’t actually support that. Neither does anecdotal evidence.” She’s observed that couples who have worked on developing a solid relationship, who know themselves and their expectations of marriage, who created a good environment in their home before they entered into this new marriage — no kids’ shenanigans can break them up.

“I really wanted to protect our relationship,” shares Tammy. “That was the most important thing to me. I saw our marriage as the tree trunk that had to continually get stronger and stronger to uphold the branches. And there were storms, but the stronger we were as a couple, the better we were able to weather those storms.”

Even though she dealt with challenges, like a stepchild with profound disabilities, former in-laws who weren’t cooperative or supportive, children from her second marriage with disabilities, Tammy noted that she and her husband almost intuitively understood that the drama going on outside of their relationship was just that — outside the relationship.

“Hashem puts a challenging person in everybody’s life, and it’s our choice what we’re going to do with that challenging person,” Tammy said. “Hashem’s perfect and just, and it’s not my business to let His cheshbonos occupy my space, my time, my mind. Thinking this way is a very freeing experience.”

“I think it’s very important to have a very good relationship with the stepkids,” says Barbara. “I do know of people who don’t, people who say, ‘Well, I married their father, and I don’t have a relationship with the kids.’ We don’t feel that way. We feel you marry into a family. That’s something we talked about while we were dating. We felt we should be involved with each other’s family and each other’s simchahs, and go as much as we can to visit the married kids.”

When it comes to children living at home with you, “If the kids have issues with their stepparent, you have to let them take care of it. Try not to get involved. Don’t try to fix everything. The issue isn’t with you. Let the two of them work it out.”

Esther suggests that, “If your stepchildren are  babies or very little, then you need to be their mother. But for the older kids, you don’t have to take the place of their mother. I can’t tell you that I did a great job of that because I’m that motherly type, that type that tells them they have to make their bed.” For her teenaged stepchildren, she says, “I didn’t act like I was their mother. I didn’t insist we sit together in shul. I let them do their own thing. I didn’t force us to become a family. I didn’t force that at all.”

“My husband stepped into the role of being a father figure to my kids,” says Tammy. “He was very respectful of his role in my children’s life. He never disciplined them, and he was never the bad guy — that was my job.” Remarking on how close his relationship is with her daughter, she says, “He’s not her father, but he’s everything she wants in a father.”

Barbara shares that, “When I met my third husband I said, ‘It’s not just my siblings you have to be involved with. I’m still close to my late husband’s family.’ They all came to our wedding. They have a wonderful relationship with my third husband, they accepted him and took him in. It’s really special. Not everyone knows how to do that. Sometimes it’s overwhelming. He said, ‘There’s so many of them!’ But it’s really nice, and I attribute that to my late husband’s parents.”

“Do whatever you can to have peace,”  says Esther. And with careful pre-planning and great rabbinic and therapeutic support, a second chance for marital happiness is entirely possible.

Adult Children as Support

Sometimes adult children are the only supports a single parent has and so even if the parent is still processing the marriage she no longer has, the adult child may push her to get remarried.  Don’t rush her, but when she brings it up, especially if it’s a done deal, try to be supportive.

A common challenge for adult children upon their parent’s remarriage is being unseated from whatever role they may have been playing in their parent’s life, whether it’s emotional, financial, or physical. If a child has brought a parent supper for two years, but after the parent’s remarriage finds she’s not invited for Shabbos, that can feel really strange. “And that’s okay,” reassures Sarah Rivkah Kohn of Zisel’s Links and Shloime’s Club. “That’s normal. That’s what happens when there’s a new relationship being built.”

She goes on to say that if you have younger siblings still at home, they may kvetch and complain to you. “Don’t let yourself get triangulated,” she says. “I’m telling you, it’s not worth it. Get an outside party who can assist and mediate. Don’t get involved!”

Wisdom along the Way

“It’s a very good idea for a couple who are getting married for the second time to start out in a new home. It’s not always feasible, but it helps a lot with kids who are unhappy about their stepsiblings invading their turf.”


“You must have a sense of humor.”


“When I moved into this house, somebody said, ‘Don’t compare. Don’t compare your late husband to your new husband.’ ”


“Everyone comes with a peckel, everyone comes with a past, and everyone is affected by their past. Just knowing that enables you to appreciate where someone else is coming from, and be more understanding of who they are. Hopefully people are in a healthy place when they get remarried, but know you may have some battle wounds, you may have some scars, they’re there.”


“New spouses should try to appreciate how their partner has grown through his challenge.”



(Originally featured in Family First, Issue 825)

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