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The Downside of Second Marriages: 3 Observations on Stepchildren

by Ray Gregoire (Mr. Boomerina)

Unlike the book “I’m OK – You’re OK,” in real life the reality is “I’m Screwed Up – You’re Screwed Up” and so are your kids. That’s just the way it is, although very few of us will readily admit it. We all come with our own baggage and preconceived ideas of how things should be, especially when it comes to stepchildren.

If you were under 25 when you got married the first time, you slowly, almost invisibly, developed your ideas concerning marriage, child rearing and finances. Your first spouse was part of that process, so he or she agreed with you more often than not; and if your spouse disagreed with you, he or she at least understood your point of view.

Remarriage after 50

Now, at 50 plus, you are a widow or widower or you are recently divorced. You and your future husband or wife have preconceived, and often unchangeable, notions of how the world should be. However, the wild card in your relationship will be your relationship with the children from your partner’s previous marriage.

You Spoiled Your Kids!

You Spoiled Your Kids!

In my opinion, stepchildren are the greatest danger to any second marriage.

Why Men Remarry

What motivates men to get married for a second or third time is quite different than it is for women.

For men it is sex, sex and companionship, or sex and shared interests. Get the point? For women it is security, security and a home, security and assistance with their children, which is quite different from what men want.

Keep your eyes wide open before you take the leap again. Not only should you pay attention to your potential spouse, but you should read the attitude of his or her children, because in the long run this will play a huge role in the success or failure of your marriage.

Observation #1: Stepkids

  • Daughters seem to have more problems getting along with new stepparents than sons do. With sons, it’s all about the money. Boys worry more about the new stepparent getting their inheritance.

Observation #2: Divorce

  • If one of you is divorced, the children, regardless of age, still dream of mom and dad getting back together again.

Observation #3: Parenting

  • You will never be as good as their real dad or mom was.

Unfortunately, it is very common for children (who are at an age that they should be independent) to be dependent on mom or dad for financial help.

These are observations I’ve made in my second marriage and I’ve seen similar issues develop in my friends’ second and third marriages. If you are at the point where you are considering remarriage, you should analyze your potential spouse’s attitude about his or her children’s financial and emotional dependency.

I’m sure several of you have different opinions. Please leave a comment to express your views.

More Articles for Baby Boomer Women Over 40:

Should You Stay Married After the Magic is Gone?

Dating for Newly Divorced Women Over 40 & 50

Divorce Over 50: Gray Divorce - The Good & the Bad

Second Marriage Advice for Baby Boomer Women Over 40, 50, 60

Resources: Photos courtesy of prshots.com.

  • Main Photo: Fashion shots from Jacamo and Dorthy Perkins.
  • Your Kids: Children's fashion photo from Sainsburys.

What do you think of this article by my husband? Do you agree or disagree? Leave a message at the bottom of the page.

Ray Gregoire is a retired executive from Johnson & Johnson.

Follow Me on Pinterest Follow My Boomer Lifestyle Blog on facebook

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  1. Beth

    Hi Ray, I think your article is pretty spot on in many areas and it would be a good article for someone thinking about taking the plunge a second time to read and pay attention to. However, I thought it was sad that you put home and assistance for the other two traits women want besides security, while for men it is companionship and shared interests. Your view on women seems to be that we only want your money. The truth is that women also want the companionship. I think shared interests would be under the umbrella of companionship, much like home and assistance would be under the umbrella of security. Therefore, it would be more accurate to say men want sex and companionship and women want security and companionship.

    You are correct in your assertion that anyone thinking of a second marriage should look at the children carefully. In my case it was my husband's child who was exceptionally spoiled. I did see this going into the marriage, but I never dreamed how much money was going to be taken out of our income before he truly saw the light and the situation improved. Now it is my child, a very stable non-spoiled girl, who needs our help because of a very unexpected divorce.. I'm very happy to say that my husband responded with generosity and love and I'm sure she will be back on her feet in no time. The point is, children, no matter how old, could still impact your marriage much more than you were expecting. But I would like to make the point that in the marriages of my friends I have seen dependent adult children from both sexes raised by either gender. In other words, girls can be spoiled and boys can be spoiled. Women can spoil their children too much and men can spoil their children too much.

    So, I find fault with your insistence that females are the ones who are spoiled and are out for your money. The article seems to reflect some anger against women which makes it unbalanced. However, the main thrust of the article, which is people going into a second marriage should observe the way their future spouse interacts with their children, is definitely correct. I think the assumption is that since the children are grown, there's no reason to worry about how they will impact your marriage. This is not true. It is always going to be a case of "love me, love my dog" or in this case, "love me, love my family." Your next to ending statement is excellent advice, "you should analyze your potential spouse's attitude about his or her children's financial and emotional dependency." If you do that and discuss your expectations and boundaries you feel should be in place for the children, you more than likely will save yourself from some potentially hurtful surprises and difficulties in your new marriage.

    • Ray Gregoire

      Beth I would agree that in many cases I have seen that it is occasionally the man that is the one more interested in the "money" however I am speaking of real life events that I was involved in. One being a spouse (not my current spouse) and one being the spouse of one of my children. In both those cases massive amounts of money ($250,000) were spent and hidden by the female in the marriage with little regard of the negative effect on the children's education, future etc.

      Yes those events made me jaded and suspicious and helped form my opinions.

      When I re-married after my wife's death from breast cancer to Tina (love her to death) we agreed to keep all assets separate and we did so to avoid either one of us from falling prey to any chance of maleficence.


  2. carole

    I am trying to reach you... I am getting married for the 3rd time.. though I am not sure the 2nd counted as it was to the same person... LOL! I found a dress I absolutely on Pinterest. When I pinned it your website came up.. I have been on the site and can't find any information about it. Can you help me? I am not sure how to tell you what dress it is as I can't seem to find a way to attach it to anything. You are welcome to view my pin under my name and mom's wedding. It is the lavender or silver looking vintage looking dress. I would love to get this dress for my February wedding. Please help if you can. thanks

    And the article is very good... I agree step children are alot to handle... I have learned a lot about my self thorugh dealing with them. thanks

    • Tina-Boomerina

      Carole, I'll try to find you on Pinterest, but I must warn you that some of my articles are older and the clothing may no longer be available online. I'll email you.

  3. Linda

    I'm 20+ years into my 2nd marriage & glad I/we toughed it out. Your article is spot-on. Remarriage with stepchildren is not for the faint-hearted.
    My relationship with my kids has stayed pretty much intact - but not after dealing with serious drug problems both of them got into. (I have to add that I have seen that happen to many of the children in blended families. We try to escape the damage divorce causes our children with exceptional parenting, but I'm convinced they were previously referred to as broken families for a reason.)
    My husband's relationship with his daughter is very strained to this day. (She's now 40 years old.) In retrospect I see that she was jealous of me from the beginning - as if her father loving me would deprive her of the love he had for her. I have tried to allay her fears, but it is pretty hopeless. After all this time, I accept that she will never "like" me and my biggest regret is that my husband doesn't have the close relationship with her that I think he had before my entrance in the picture.
    You always wonder if any of these things would have occurred without the divorces and subsequent remarriages. Would my kids have gotten involved with drugs anyway? When my husband realized how self-centered his daughter was, and refused to comply with her narcissistic demands, would their relationship have soured anyway? We will never know and have resolved to concentrate on our relationships with each other.

    • Tina-Boomerina


      I am so sorry to hear about your problems. I wish I could just say "the magic words" and make every stepfamily into The Brady Bunch... complete with maid.

      Tina Boomerina