Second Marriage After 40: 10 Questions To Ask Yourself

second marriage after 40

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

There is a reason the divorce rate for second marriage is over 70%. In fact, some studies even claim second marriage failures as high as 80%. That doesn’t speak well for second marriage – especially second marriage after 40.


If you’re considering second marriage after 40, or even if you are just dating, with second marriage as a possibility someday, how do you make sure you end up in the 20% of couples who get the happily ever after?

The answer is simple: If you want a good second marriage after 40, MARRY THE RIGHT PERSON.


Here are 10 questions to ask yourself to decide whether or not second marriage after 40 is right for you.


        1. Are the two of you alike?

That means do you have similar likes, core values, and interests? Do you enjoy spending time together and do you like to do the same things? Do you view world issues the same. Are your values in raising your kids similar? The list goes on. The more alike you are, the better chance your second marriage after 40  will work.

        2. Do You Trust Him/her? I mean really trust him/her?

 When things get a little rough, is he going to walk away? Do you also trust him with finances and other household decisions? Do you also trust that he will be loyal to you, i.e. not cheat?


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       3. Is He/She Your Best Friend?

Can you talk to this person about anything?  Do you feel like there isn’t one thing you don’t feel comfortable discussing with him? Does he get you? Do you get him? Do you enjoy him? Does he enjoy you?


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       4. Does he/she have a good relationship with his/her kids? 

If he doesn’t, that might make things difficult and complicated. Can you handle stressful times? Remember that his/her kids come with them.

       5. Is He/she Thoughtful and Kind? 

Is he considerate? Does he do sweet things for you with no agenda? Does he treat others in a kind way?

      6. Do you want to take care of him and can he handle it? 

A woman who truly loves a man wants to take care of him and vice versa. That is not possible unless the man/woman is willing to let her. In other words, he has to be someone who isn’t afraid to show vulnerability and the need to be loved and cherished by his wife.


       7. Does the person really want the marriage? 

“Marry someone who loves you more than you love him,” my mom always used to say to me. Although I believe that both people should be madly in love with each other when getting married, there is a little truth to the fact that the guy really has to be over-the-top and completely committed to the relationship and the marriage. He has to really, really want it. You shouldn’t have to put pressure on him to get married. He should be the one pursuing it. He should adore you. You’ll be able to feel it if he does.


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        8. Do the two of you have the same vision for your future? 

Everyone sort of has a retirement plan, right? I mean, not a specific plan, but a general idea of where they want to end up. Is that plan the same for the two of you? Think about it. This is the guy you are going to grow old with. Does he want to move to Arizona but you want to move to Florida when you are retired? That’s a problem. It’s worth discussing it.

        9. Is the sex is great? 

It’s important that the two of you are on the same page in bed. Sex is a form of communication. It connects couples on a different level. It fosters a closeness and a bond that is very important in a marriage lasting.

        10. Do his kisses take your breath away? 

Does this really need an explanation?


The thought of second marriage after 40 can be very scary to divorced men and women, and understandably so. After all, you’ve been through a long, heartbreaking breakup, followed by a legal battle that was most likely frustrating, expensive, infuriating, and scary. Why on earth would you want a second marriage?? Because, with the right person, marriage could be a totally different and better experience. In other words, he needs to be second marriage material.

Like this article? Check out, “Thinking about a Second Marriage? Topics to Discuss with Your Partner”

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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:

    10 Responses to “Second Marriage After 40: 10 Questions To Ask Yourself”

    1. Jason Silver

      Great list! Easier said than done obviously… One thing missing here is how both people define their relationship with money and how they want to use it.

      • Holly Downs

        This may be included in question #8 however I agree it is a stand alone issue and one that needs to be understood. I am a total saver and my current bf is not, this causes me a great deal of anxiety. He said not a problem, he will just give all of the money to me. This then makes me feel alone in the responsibility of dealing with money and making financial decisions.

    2. Al

      So the answer to all the questions from this man is yes!!!! The kisses especially but beyond yes on all of them except one. I have erection problems. And that is a deal breaker.I don’t drink smoke do drugs . I make close to $200000. A year and like sports travel writing love poems and holding hands. Am I. Just a loser?!
      Oh and I am fact I was called the “complete package” and I would never believe it. I am humble and can be shy. My kidneys ache constantly with cystitis or something and I have ED.drugs help at times but not all the time. Do your rules apply even for the 50 year plus womanlooking for a man. I backed away from real love because I think she deserves natural sex from a man still able. I owed that to her in my love for her. I want her to be happy.. I am however destroyed as a man and a human.I lose .it hurts

      • Jackie Pilossoph

        I feel sick that you feel that way. Ask any woman over 40 and she will tell you that sex is such a small part of a true, meaningful romantic relationship. And, sex is so much more than intercourse. I’ll take great kissing any day of the week! Have you ever considered going to therapy and talking about your mindset? You should. You are very much not alone. I think i read somewhere that 60% of men over 50 have a hard time maintaining an erection. You sound like a great guy! Beleive that!!

    3. Lori

      I really like your site but air have to admit to being utterly frustrated at the overwhelming amount of grammatical errors in almost every article. I know it is cheaper to get content writers from foreign countries or whose first language isn’t English but please…for your sake and credibility, proof read before posting!

      • Jackie Pilossoph

        OK…well just to be clear, I am writing all the content, so you can blame the overwhelming amount of grammatical errors on me, 100%. I’m doing my best with the time I have and hopefully I am helping others. That is my number one priority.

        • Pamela

          Love your advice & site and didn’t notice any grammatical errors. I wasn’t looking for them! Keep doing your thing!!!

          • Leslie

            I have to second Pamela’s reply regarding Lori’s comment. I love your advice and wonderful, helpful insight. I didn’t notice any grammatical errors. Nor was I looking. I can’t tell you how much help you have given me. Thank you!

            • Jackie Pilossoph

              Awww, thanks so much for the support! Very thoughtful of you to reach out. xo

    4. Claire

      I actually did notice the grammatical errors as well – I am a teacher, what can I say? I also write in my “free” time, haha. Feel free to send any articles to me for a free grammar/spell check if you wish. And I do appreciate the content. Bizarre time in my life for sure. Thanks.


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