Second Marriage: Should You Take That Chance?

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

second marriage

I am a huge fan of second marriage, and I love love love hearing those happy stories. That said, I think I read somewhere that 72% of second marriages end in divorce, which makes me sad. If someone asked me what the key is to ending up in the 28% of second marriages that succeed, I would show that person my Love Essentially column, published today in Chicago Tribune Pioneer Press. Here it is!

30 Questions to Ask Yourself Before You Pop The Question  by Jackie Pilossoph

I know a couple who has been happily married for 15 years and who have three children. What I recently found out about the husband was my inspiration for this column.

He told me while sitting in the stands at our sons’ basketball game that he was engaged a couple years before he met his now-wife, and that he broke it off because he knew in his heart it wasn’t right. When I asked how he came to the realization, he said “I didn’t ask myself the right questions before I proposed.”

So, what are the right questions? Here are 30 I think anyone who is considering a lifetime commitment should ask!

1. Why am I getting engaged now? In other words, is it because I don’t want to lose her? Perhaps I am getting married because I want kids? Or, is it because I am ready to make this commitment and this is the right person for me?

2. How does this person handle a crisis? Does he/she fall apart or can they deal with pressure?

3. Does this person truly love me or does he/she just want to be married?

4. Do we have fun together? Can we sit in a room with one another and do nothing and still feel comfortable and happy?

5. Do we share similar goals and dreams? Do we want the same things long-term?

6. How is his/her family? Do they feel like family to me already? Do I want to spend time with them? Do they want to spend time with me?

7. Did my future wife/husband have a happy childhood? If not, has he/she gotten help for issues that might present a problem in the future?

8. Are we both on the same page as far as if we want kids and how many? If so, have we talked about religion in raising them?

9. Is my future husband/wife motivated professionally? Does he/she enjoy their career?


10. When we fight, are we able to talk things through constructively? Or do we scream and shout and/or have long periods of silence afterward?

11. How are we together in bed? Are we both satisfied and happy with our sex life?

12. What is her mother or his father like? He or she will most likely turn out just like that person.

13. Does he/she have addictive tendencies? A little too much wine at night or excessive gambling can turn into something larger later.

14. Does he/she make me laugh?

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15. Do we enjoy similar books, movies, hobbies, tourist spots, sporting events, etc.?

16. Is he/she my best friend? Do I feel comfortable confiding in this person no matter what?

17. If it’s a second marriage, does this man/woman love my children? Does he/she have the desire to offer them warmth and support?

18. Is my gut telling me he/she is the right one, or am I convincing myself of it?

19. If I get sick, will he/ she take care of me? Will I do the same for him/her?

20. If we have a difference in opinion, is he or she open to hearing my side or are they defensive and closed-minded?

21. Does this person have good values? Any red flags on their opinions of anything we’ve ever discussed?

22. Does he/she have a social life outside of me?

23. How do I feel about the friends that he or she has chosen?


Click here to read the rest of the column, published today in Chicago Tribune Pioneer Press. The last four are my favorites!

Buy novels by Jackie Pilossoph



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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorce is a journey. Live it with grace, courage and gratitude. Peace and joy are on the way! Jackie Pilossoph is the creator and Editor-In-Chief of Divorced Girl Smiling. 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.

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