Second Marriage After 50: Is It For You?

second marriage after 50

By Jackie Pilossoph, Creator and Editor-in-chief, Divorced Girl Smiling site, podcast and app, Love Essentially columnist and author

Recently, four couples, including myself and my boyfriend, met at a bar to have some drinks. Of the eight people who were there, all are divorced with children, and seven out of the eight are over the age of 50. None are in a second marriage. Of course, I brought up the subject of second marriage after 50, wanting to hear their thoughts and opinions.


Of the four couples, my boyfriend and I have been together the shortest amount of time. Another couple has been together for six years, and the two other couples have each been together for eleven years. Again, none of us are in a second marriage or engaged.


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I know for a fact that one of the women would like to be engaged, but her boyfriend has said he does not wish to be married again. Ever. He said he is too scarred from the pain of his first marriage.

Another couple, who lives together decided to label themselves as “life partners” and stay unmarried permanently. The third couple said they are happy with the way things are, that things are very complicated with their kids, and that for now, they do not wish to get remarried for that reason. They said marriage is a possibility, but not for the foreseeable future.


As for my view on second marriage after 50, although I definitely think I’m with the right person, and that a marriage to him would work, both of us don’t feel ready to get married or to move in together right now for a couple reasons.

1. We have such a wonderful relationship, why change anything?

2. The blended family situation scares me. I don’t know one person who got into a second marriage after 50 who isn’t miserable when it comes to the blended family. Even if the couple is still happy together, they will tell you it’s very difficult living with each other’s children.

So, are my friends and I the norm? Do the majority of divorced people shy away from second marriage after 50?


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There are countless statistics about divorce and second marriage after 50. Let’s start with divorce. According to The Pew Research Center, divorce over 50 (also known as “gray divorce”) is on the rise, with the divorce rate in this age group doubling since the 1990’s. But remarriage is also on the rise for men and women over 50 in the US.  In recent years, 67% of men and women aged 55-64 remarried, up 55% from 1960.


The case for second marriage after 50 is strong. There are tax benefits, insurance benefits, and social security and pension plan benefits. Also, God forbid one person gets sick and/or is hospitalized, the other person can make medical decisions that someone who is just a girlfriend or boyfriend cannot.


There are also reasons why someone would want to be in a second marriage after 50 that have nothing to do with practicality, but rather with the beauty of tradition. In my opinion, there is something deep and meaningful about standing up in front of a crowd of family and friends,  saying vows of commitment to each other, and promising to love and cherish each other, especially through the difficulties that can come with aging.


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So, why wouldn’t someone want to tie the knot again? The case for staying legally single is also pretty compelling. There’s the “been there done that,” attitude, where the mindset is that marriage wasn’t a particularly great experience and there’s no need to do it again.

Also, many people think there is no need to get married if you aren’t planning to have more children. People also don’t want the stress of blending families—even if the kids are older. In other words, the Brady Bunch mentality doesn’t appeal to them.

And then there’s money. Anyone who is divorced will tell you that the stress of possibly co-mingling financesagain can be overwhelming, no matter how much you trust someone. Even with a prenup, marriage can feel scary in this regard.


I think the decision to get remarried is entirely personal, every situation is unique, and that there are so many factors to consider. In my opinion, what’s most important in a relationship after a divorce is happiness. Ask yourself:


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1. Does this person make me happy?

2. Does he or she respect me and vice versa?

3. Do we have fun together?

4. Is this relationship easy?

5. Do I like him or her?

6. Do I adore him or her?

7. Do I like myself with him or her?

8. Do I trust him or her?

9. Would I take care of him or her in sickness and vice versa?

10. Do I want to grow old with him or her?


If you can answer yes to all of these, than you are with the right person, whether you have a ring on your finger or not.

Like this post? Check out, “Dating After Divorce: Advice, Tips and Why This is an Exciting Time”



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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorced Girl Smiling is here to empower, connect and inspire you. Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling, the site, the podcast and the app. A former television journalist and newspaper features reporter, Pilossoph is also the author of four novels and the writer of her weekly relationship column, Love Essentially. Pilossoph holds a Masters degree in journalism and lives in Chicago with her two teenagers. The author of the novels, Divorced Girl Smiling and Free Gift With Purchase, Pilossoph also writes the weekly dating and relationships advice column, “Love Essentially”, published in the Chicago Tribune Pioneer Press and the Chicago Tribune online. Additionally, she is a Huffington Post contributor. Pilossoph holds a Masters degree in journalism from Boston University.

4 Responses to “Second Marriage After 50: Is It For You?”

  1. Christine Lewis

    I disagree with number one. It is not your spouses job to make you happy. One reason marriages fail is the unrealistic expectations we put on the other person. Not sure what she means by Is this relationship easy. Marriage is hard work. Just my opinion.

    • Jackie Pilossoph

      I respect your opinion and you are right. Marriage is hard work. But, there is a difference between wanting to do the work and giving up because it’s just too difficult all the time. Anyone who is in a healthy, happy romantic relationship will tell you “it’s easy.” Not that they mean they don’t have to make an effort to keep things that way, but for the most part, things just go smoothly with the other person.

  2. Byron

    “Is it for me” is an important question to ask. With “happiness” now clarified, I’d like to nominate “trust” as the next test that bears deeper consideration. It’s a frequent topic of conversation in the group of “over-50″s I find myself hanging out with.

    We always want to consider whether we “can trust them?” That might tend to suggest that we’ve found someone to give the tests here to? But there’s another side of this that might better determine whether we’re in the dating pool at all: “Am I someone who can be trusted?”

    Most of those in my group of friends – men and women – aren’t so much worried about moving up in their careers, about parenting and household responsibilities that come along with kids. We talk about what retirement is going to look like. We wonder what grandparenting is going to look like. We don’t have the time, money, or energy to tie ourselves and our families up again in a divorce. And if we truly can find happiness within ourselves, it’s that much more difficult sometimes to see why we’d want someone else in our life – and yet that’s often attractive all on it’s own.

    How are we with money? Do we pay for our fun before we pay the bills? Do we squirrel away what’s leftover for that fishing rod or pair of shoes we know our partner won’t exactly be thrilled about? How are we with our friends? Are we someone different than we are with our partner? Do we badmouth, criticize, or make fun of them when they’re not around? “Romance” is great, but how are we when there’s hard relationship stuff going on? When that fishing rod or pair of shoes has been discovered by our partner? When we disagree about something else? Can we disagree without attacking our partner? Are we prone to cutting our losses at that point and finding someone else, or is that when we take responsibility, apologize, and find a place to move forward from? This is the person who could be left with two doctor opinions that you’re not going to make it, and one that you will – and then the decision whether or not to pull the plug?

    Being trustworthy has to come before someone else trusting in us. If we can’t live up to what we expect of them, we shouldn’t be wasting their time.

  3. Kim

    I loved your article ! I do agree, getting remarried for the second time is my fairy tale because I finally found the one man I want to spend my life with. But I do not need to be married to love him forever or trust him or vow to take care of him or vice versa 🙂


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