We’ve all heard the expression “third time’s a charm,” right? Which of course means that once you’ve attempted something several times unsuccessfully, you’ll have a more positive outcome the third time.

While this may hold true if you’re trying to do simple things like grow an herb garden, take an exam, or pick out the right paint color, it’s not quite as simple when it comes to marriage.

Statistics for divorce rates vary based on the source, but generally, we see reported that in the U.S., 41-50% of first marriages, 60-67% of second, and 73-74% of third marriages end in divorce.

To complicate matters, it’s reported that the children of divorced parents are prone to divorcing four times more than the children of couples who are not divorced. So, what do you do in an era where longevity is re-defining every element of our lives and every social and economic system? We hear about the rise of “gray divorce” more and more in the media with the divorce rates of older couples, but you really don’t hear much about the notion of “gray marriage.”

Marriage is complicated the first go around, but let’s add to the complication blended families. Blending his children with hers and maybe even ours adds some very special needs to an already interesting mix. I’m reminded of a couple I worked with several years ago who requested a retirement income plan and analysis to make sure they didn’t run out of money during their retirement.

More importantly, they wanted to leave an inheritance for their children. Their story struck a chord with me and is relevant to lay a foundation for the things that must be considered before you tie the knot a second, third or perhaps a fourth time. Let’s call them Tim and Alice (not their real names) for the purpose of this example. Tim and Alice have been married for 10 years when I first met with them. They relocated to Florida for retirement, purchased a home where they both contributed half. Tim had two children and Alice had one child. No problem, right?

One would think this is a simple retirement and estate planning scenario. But, don’t get ahead of yourself. I inquired if they had legal documents to protect against probate and to ensure the estate was distributed in accordance with their wishes and desires. The looks on their faces told me I had opened up a can of worms. This couple who were very pleasant and full of joy when they walked into my office, ended up in a conflicted, non-compromising position filled with confusion and anger.

The problem?

They realized they had never discussed estate distribution before the marriage. Nor had they discussed money matters before they tied the knot. I tried to facilitate the discussion, but the matter simply got worse as I addressed more factors they needed to consider. You see, Tim felt the distribution of anything left behind would be a third to each of the three children. On the other hand, Alice felt like it should be 50% to his two children and 50% to her son. There was no pre-nuptial, and now if they wanted to resolve this conflict, each one will need to hire their own attorney and pray they can reach agreement for post-nuptial.

A few weeks after this visit, I called to check on them to see how things were going and if I could be helpful. Essentially, they didn’t want my involvement at all. According to Alice, “We never had any problems until we came to see you, and now we fight all the time.”

Really! This is what happens when you don’t discuss money and other financial matters before you tie the knot. I’m sure I created the pain, but truthfully, I’m glad I did!

Sooner than later when one of them unexpectedly passes on and at that emotional life event, the surprises arise. So, do yourself and your family a favor; have these discussions and open up the dialogue before you tie the knot, especially if you have children from previous marriages.

Remember, longevity may very well have you married not once, or twice, but perhaps three or four times. I know 90+ year old’s who are tying the knot for the second time, so be prepared.

Here are seven considerations I’ll invite you to think through before you do tie the knot:

1. Talk Money: Discuss your financial assets, what the purpose of your money is, how you’ll manage your individual assets, joint assets, etc. The financial stress is significantly higher in second marriages than in first marriages so be thoughtful about what you will do. If you had financial stress in your first marriage, make sure you reconcile this because if you were the source, then you just might be bringing the same stress into the new marriage.
2. Consider Pre-nuptial Agreement: I’m not an attorney, accountant, or an investment advisor, but I do know retirement planning and all the things that must be considered. I’m not suggesting this is right for everyone but aside from the stigma associated with pre-nuptials, it does offer the opportunity to openly discuss your individual assets, going into the marriage and what will be protected for heirs, and what will be considered joint assets. It’s easier talking about these before you tie the knot because doing so after the fact is more costly and a high risk road to open, trusting and honest communications.
3. Discuss How Two Families Will Be Merged: There are traditions that families honor so make sure you’re aware of each tradition and how to preserve them while creating your own new traditions. For example, celebrating holidays when families are disbursed can be costly if you have to have two or three holiday celebrations. Make sure you budget for this, decide who will pay for what, and create the boundaries before you tie the knot.
4. Fully Disclose Debt, Financial Obligations, Credit Issues: Many men and women end up with credit issues, bankruptcy issues, etc. while terminating a previous marriage. Also, you may be entering the new marriage with financial obligations from the previous marriage. In the spirit of full disclosure, you’ll need to openly discuss these, own up to your obligations and credit issues, discuss what you learned, and what will be different. If there are spending patterns and behaviors that created a problem, ask for help with these behaviors and check frequently so you don’t create more credit issues.
5. Agree on Beneficiary Designations: Retirement accounts, IRA assets, life insurance policies and annuity contracts are all distributed based on the beneficiary. Do a beneficiary audit and modify based on your agreements. How would you like it if an ex got some of your hard-earned money? Don’t assume you’ll do it later, because life has a way of throwing you curve balls.
6. Update your estate planning documents: All of your legal documents need to be updated to ensure they represent the wishes and desires of the new marriage, protect heirs from previous marriages, etc. That means you’ll need to update wills/trusts, healthcare and financial powers of attorney, and have appropriate living wills for the state of residence. Legal planning is a bit more complicated with second marriages, particularly if you have disabled beneficiaries, or special needs for a beneficiary. Seek the proper legal counsel to validate what you need, a will vs. a trust, the use of the home, etc.
7. Complete an Insurance Audit: Make sure you are properly insured with life insurance, health insurance, long term care protection, auto and even your property and casualty insurance. Don’t leave a stone un-turned because it could be the very stone that brings great heartache. Work with an insurance professional because the addition of life insurance, particularly if new mortgages are acquired later in life, will need to be considered based on your life needs.

These represent the essential considerations before you tie the knot. The discussions could be difficult if not challenging, but trust me, they will be more challenging after you tie the knot.

You don’t want any surprises as you journey through the blissful years of the new marriage so be thoughtful not to rush down the aisle before you’ve spent quality time with these discussions. Say, “I Do” to being prepared and ready for every obstacle on your path to living happily ever after.

Jeannette Bajalia, author of "Retirement Done Right" and "Wi$e Up, Women," is president and principal adviser of Petros Estate & Retirement Planning, where she has designed and implemented innovative estate-planning solutions for clients and their families. She also is founder and president of Woman’s Worth®, which specializes in the unique needs facing women as they plan for their retirement.