Second Marriage After 50: Topics to Discuss

second marriage after 50

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

A member posted this message on the DGS Facebook Group page, regarding second marriage after 50:

What topics should you make sure you and a partner discuss before you consider a second marriage after 50? I’ve read articles but they all address a first marriage when you’re young. I’d like topics to make sure we discuss at this stage in our lives. We are both 50 years old, we both have careers, and we both have older kids.

Here’s my advice:

Second marriage after 50! Wow! Isn’t it wonderful? Just a few years ago, you got divorced, and probably never dreamed about a second marriage. Well, here you are: excited and giddy and happy, yet I have to believe that every divorced person walks into a second marriage with a little bit of skepticism, a certain amount of fear, and on a positive note: a lot more wisdom.

A lot of divorced couples find a happy, healthy romantic relationship and stay in it for years and years without feeling the need to get remarried. There is certainly nothing wrong with that, and if others start pressuring you, just smile and say, “We’re really happy.”


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But let’s say you now have a ring on your finger and second marriage is imminent. Let me answer my reader’s question and address what topics you should discuss before jumping back into marriage.

Here are 5 topics you should discuss with your partner before getting into a second marriage after 50:


1. The finances.

I would have to say that finances are the number one thing needing to be discussed when going into a second marriage after 50. First, sit down and have a detailed conversation–as uncomfortable as it may be, about who is paying for what. What happens if one loses his/her job 0r is unable to work? Having all the details worked out before the nuptials will take all the pressure off and avoid any surprises and/or potential arguments.

“What’s mine is yours and what’s yours is mine,” is a really really bad attitude in a second marriage after 50. Once you have the somewhat awkward conversation, everyone knows what to expect and goes into the marriage with no unrealistic expectations.


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2. The kids-no matter how old they are.

What if Joey (who is 27) needs to move back home for a few months? Is the other person OK with it? What if Jenny wants to have dinner with her dad once a week without you? Will that work for you? Kids, no matter how old they are, sometimes have issues with step parents. You have to be ready for that and know going into the marriage that life when it comes to his/her kids, might not always be rosy.

Remember that when you marry him or her, you are marrying the kids, too. If you truly love him or her, you will put up with the sometimes bad behavior that step kids can exhibit, and appreciate them for who they are, without unrealistic expectations.


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3. The household.

Who is doing the cooking? Who is cleaning? Are you OK with his wet towels on the floor? What can you ABSOLUTELY not put up with? Tell him now or forever hold your peace! Actually, that’s not good advice. When you do move in together, if something is bothering you, tell him or her in a nice way, immediately. Don’t let things fester and build up resentment.



Also, who is doing what chores? Lastly, have a conversation about what your daily life is going to be like. Tell her now if you think you need a little alone time after dinner or during the weekend. Remember that the newness is going to wear off, and you will be married to the real him or her. That’s not a bad thing, it’s just reality.

4. Retirement.

Having a conversation about retirement is huge! Does he know when you want to retire? Do you have this idea about moving to Florida in a few years? If so, better to bring it up before the wedding, so just in case he says “Let’s move to Arizona,” and you hate extreme heat, you don’t find yourself in a relationship that is geographically undesirable! Also, it’s important to share retirement funds. Knowing how much each person has in their retirement savings will help you know what you are getting into.

Then, you have to talk about who will be supporting who and if you are OK with that. Also, what happens if one of you gets sick or gets to the point where you need full-time help (meaning a caregiver)? Many couples decide to take out long-term care insurance that will pay for a caregiver or for the person to live in an assisted living community. It’s a horrible thought, but better to be prepared!


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5. Will and Estate Planning.

Perhaps the most uncomfortable discussion to have is the one about your death. But, it’s also very very important! First off, both people getting married should have an updated will and trust. That’s a given! Secondly, let’s say you are moving into your new husband’s house and his name is on the deed. You might want to have a document drafted about him allowing you to live in the house for the rest of your life, should he die first. It’s OK if both of you decide to leave everything else separately for each of your kids. But, it’s a discussion that must be had. Helpful hint: have the discussion over a glass of wine or two, and make it a positive one. Remember that being prepared is everything!


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In closing, 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.


I am a huge fan of second marriage after 50, IF (and this is a big IF) the situation is right, the timing is right, and the people are getting married for all the right reasons.

How do you know if you are getting married for the right reasons? Ask yourself these 10 things:


1. Does this person make me happy 97% of the time?

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 when I am 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, then you are with the right person, whether you have a ring on your finger or not.

Like this post? Check out, “9 Signs of a Healthy, Happy Romantic Relationship”

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    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

    5 Responses to “Second Marriage After 50: Topics to Discuss”

    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 🙂

    4. Ann

      I would agree with the thought that second marriages are difficult and require a lot of commitment and communication. In my cases it is sometimes a weekly struggle with drama introduced by one of our 6 adult children. I never want to make him choose between his children and me, but wrong life choices are always going to be wrong. The trick is open conversations about right and wrong, sharing experiences from are past and not pointing fingers. Allow him the time to think the situation through, and right always prevails.


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