A Prenup Survivor’s Story: Calling all women entering a second+ marriage!

Feb 19, 2021 | Finances, Prenuptial Agreements, Second Marriages

At the time, I was not totally sure if I should be excited, or terrified, but there it was- at forty-five, I was getting married – again.

My name is Debbie and I’m from Santa Clara, CA. I have two beautiful “kids” ages 14 and 17, whom I’ve co-parented with my ex-spouse for almost a decade now. After a few years of marriage, we decided to divorce – and it was really hard financially, physically, and emotionally – especially for our (at the time!) baby girls. After giving that relationship my all, I just knew it would be better if we went our separate ways.

My ex-husband and I are amicable and both share a deep amount of love and respect for our two daughters. We have found a way to parent them and keep our family “together” while also being realistic about our individual needs as well, and our desire to move on with our lives.

My boyfriend (now husband) Rick and I met at my oldest daughter’s volleyball tournament. His daughters played against mine and after a few tournaments, we really got to know each other. Our girls became close, we became close, and decided to actually become a couple. Rick was also divorced from his first wife but he wasn’t so lucky with his co-parent. His ex-wife prefers to hold grudges and does not have a very healthy relationship with Rick – regardless of their shared interest in their kids.

Rick and I had been together for about five years when he brought up the idea of getting married a few times. Initially, I was hesitant – this is because I am in my mid-forties. I have already had kids. I have already done the “susie homemaker / soccer mom / working mom-superhero” routine. I was not really looking to “settle down,” as I was already “settled down” – just not married.

And, truthfully? I’ve been working the corporate ladder for almost three decades now and I have enough wealth accumulated to cover both of my daughter’s private school tuitions, endless living expenses, my four bedroom home, our four cars, and at least two family vacations (all inclusive) every year since they were born – all with a very healthy retirement plan. My income is the highest it has ever been.

Between you and I, I was scared shitless of marriage, due to the fact that I did not want to give away half of everything I had worked for if Rick and I were to divorce in the future. I didn’t think we would, of course, but once you have been down the divorce road, it is hard not to think this way.

To get you up to speed and to share my story, here’s his viewpoint, my viewpoint, and how we moved forward on the topic of marriage.

[Rick’s viewpoint] – “In a marriage, we should share everything.”

Yes – even in our mid-forties, and after two divorces (between us) Rick still believes that we should still share everything.Even though he already had kids too. Even though he has an ex that he would rather never hear from again. And even though he too has done the soccer games (and now volleyball) and the whole “smokin hot husband” vibe (or so he claims!).

My heart said, “this is actually really romantic and cute,” but my head said, “oh hell no, I’ve seen this pony show one too many times to fall for that line of thinking.” When Rick would bring up marriage, he regularly told me that “he wants to share everything out of love, and being together means sharing together.” I have to be honest- I could not argue with that, as that is exactly how I felt the first time I got married too. My heart led that time and I ended up paying for it during a hefty divorce with my ex-husband. And the only thing I wish I would have done differently? Get a prenup.

So, you wont be surprised that Rick didn’t respond well when I brought up the idea of a prenup.

His response was something along the lines of: “A prenup means we are expecting to divorce.”

Like classic PTSD, I went back to my virgin spouse self and I remembered feeling this way also. I remembered feeling like a prenup was out of the question because it basically meant that we were preparing for the inevitable – so I couldn’t fault Rick for feeling this way.

Naturally, I felt defeated bringing it up because it made both of us uncomfortable, even though we are both veterans at the marriage and divorce show, and have both seen firsthand how painful they are (both emotionally and financially, not to mention the lasting effects that it has had on our kids).

The only way that I was going to be able to get through to him with a prenup was to express my detailed feelings about why a prenup was so important to me, and most importantly, to my kids.

[My viewpoint]: “I worked all my life, you weren’t there for it, why would any of my assets go to you and not my kids?”

This doesn’t seem far out to me because it is my second marriage – and because there are more people involved in this marriage than my previous marriage, (and his as well), so it made perfect sense for me to protect my kids – financially and emotionally – while he also protects his.

In particular, my children were with me during really hard times – the divorce, rebuilding our family unit, family therapy sessions, counseling at school, financially burdens, etc. You name it, we felt it (and it still stings to this day).

My girls have a right to claim my wealth and assets as their inheritance in the event that I pass and I don’t want to complicate this by bringing in another person (whom was not with me during these hard times).

Rick is a reasonable, well-informed individual, who has personal experience with divorce, and I wanted him to fully understand this concept before we dove into another marriage. After discussing this openly over a few months together, Rick came around and realized that this was very fair (and actually enlightening for his kids as well).

What we included in our prenup

Rick compromised and we decided to move forward with our prenup. The major topics we wanted to discuss were fairness, equality, and inheritance. In particular:

  1. Keeping inheritance for our kids (Debbie’s inheritance goes to Debbie’s kids and Rick’s inheritance goes to Rick’s)
  2. All property (ie money) will be considered separate (unless otherwise specified and placed in our joint bank account for shared bills – PG&E, water, entertainment, etc.)
  3. Our prenup would expire in twenty years from now when we are entering our retirement ages of 65 and 67, per a sunset clause.

And that’s about it.

Our check-in point and the sunset clause were good areas of compromise to get Rick on board and feeling more comfortable with the idea of this prenup.

Our prenup is designed for protection, prevention, and compromise

Because in the end, we didn’t want to deal with the messy divorce proceedings that come with separation, and we really didn’t want the hefty lawyer bills that took years to pay off (my previous divorce cost my ex-husband and I $15,000 – each).

Protection from any financial triggers that could arise in a marriage – like one spouse overspending, an unexpected health expense, or debt

Prevention from divorce or separation by forcing us to have hard conversations early and often (instead of waiting when it’s too late and we are in the thick of an unforeseeable event like infidelity, addiction, or incompatibility).

Compromise because no marriage can survive without it – and this prenup forced us to work together on our newly blended family and compromise on behalf of everyone involved.

Also, we realized that second marriages end in a higher divorce rating than first marriages, our kids are entering this marriage too, and we have more to lose as we age. After having some tough conversations with our divorcee thick skins, we realized that a prenup was worth its weight in gold for the pure fact that it saved us a lot of heartaches and headaches that come with getting divorced.

As for his romantic heart, I feel really lucky to be able to marry into it, because no one should feel bad about falling in love again in their mid forties, and going for a second marriage (even if you have already done all of “it” already).

Getting a prenup was the best decision we ever made because it gave us the opportunity to lead with our heads and our hearts. Without going too far off on the spectrum with heart, we were able to get a good balance of what matters for us as individuals emotionally and intellectually, and what matters for our kids emotionally and intellectually as well. Prenups enforce a great foundational building block that requires empathy, introspection, and intellect that if taken seriously could account for a major relationship breakthrough later.

We both know that no relationship is perfect, and we are absolutely going to disagree on things – like money, dinner, how to parent our girls and grandkids (hopefully one day), and we want to make sure that we discussed the hard stuff early and often so that if it comes to fruition, we are armed and ready to protect ourselves as safely and fairly as possible.

In a nut shell…

If you’re entering your second marriage, congrats!

It’s not “too late.” You’re not “too old.” And you’re not “starting over.”

The only thing that is “too” anything is not getting a prenup.

It’s too risky.

Getting married, whether it’s for your first or tenth time is exciting, so be excited about it and go all in with those big hearts of yours. However, your heads cannot be ignored as divorce, separation, death, and so many unforeseeable events can occur in this crazy thing we call life. If you’re entering your second marriage, get a prenup. If your soon to be spouse is entering into their second marriage, get a prenup. It only costs a few hundred dollars compared to the thousands, upon thousands, you will pay in divorce – through lawyer bills, a new down payment, new furniture, and ultimately a new beginning.

If this is a second marriage, the data is stacked higher against you, so protect yourself, prevent divorce, and create your compromises with a prenup (so you’re never put back in that awful post-marriage rebuilding mode again).

The good news is that there is a really, really simple solution to getting a prenup (and you can start it the second you stop reading this from the chair that you’re sitting in now).

HelloPrenup is a platform that is designed to work with second marriages (and beyond). Whether you both are entering into your second marriage, or you’re entering into your first, HelloPrenup’s easy-to-use questionnaire will address all of your property needs, your inheritance for any kids, infidelity clauses, health insurance clauses, and so much more.

With a highly customizable prenup from HelloPrenup, you avoid the billable hours associated with a traditional attorney, streamline the process from the comfort of your home, and can keep the conversation between the two of you and your kids while documenting all of your wants and needs together as a family.

Simply make a free account, go through the questionnaire, notarize with your favorite notary (we prefer Notarize.com), and prepare for your wedding. It’s that easy, and it saves you so much time, money, and heartache down the line.

Congrats on your second marriage. My gut tells me it’s going to be much, much better the second time around.


Two times the charm.


You are writing your life story. Get on the same page with a prenup. For love that lasts a lifetime, preparation is key. Safeguard your shared tomorrows, starting today.
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1 Comment

  1. Would you be interested in coming onto a podcast to talk a bit more about your story? If you’d like to remain anonymous that’s totally possible! It’s called Lovestruck Daily, and we seek out compelling, unusual love stories just like this one. We’d love to hear you tell it! Please email at the address below if interested.

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