When was the last time you really checked in with your spouse about your life, your marriage, your sex life, your kids, and even your dreams? If you are anything like Scott and me that answer would be, “Not for a long time”. Sure we communicate about all the hot topics in our life as much as possible, but the opportunity to dive deep isn’t as often as it should be. A few years ago, however, we were inspired by someone to change this and that is how our version of the Couple’s Retreat came to be.
Back in 2019, Scott and I attended a Vistage retreat, (which is a business group Scott belongs to), and we heard a speaker discuss something he called “The Couple’s Retreat”. The speaker (Eric Coryell) explained it was an annual thing he and his wife did where they went away for a night or two and really talked, shared, and connected. He gave us a handout with a list of questions on it that they brought with them every year to spark conversation. His speech ignited a fire in Scott and me to give it a shot, so back in February of 2020, we completed our first Couple’s Retreat. Scott and I booked a weekend away just the two of us. We enjoyed time alone and we also spent a couple of hours throughout the weekend answering the list of questions. We found a lot of value in the questions and felt that it set us up well for the upcoming year. We decided it was something we wanted to prioritize every year.
I am happy to say that we just completed our 3rd annual Couple’s Retreat. This year, however, we did make some tweaks and additions to it. Our retreat had three components that we found worked really well for us and I hope you will find value in them as well. Here is how we structured it:
The 100 Dreams List
I cannot take credit for the 100 Dreams List idea. A mentor of mine shared this with me. It is something she and her husband have done every year and over time their lists have ebbed and flowed.
Scott and I decided to start our Couple’s Retreat this year by doing this exercise. We both sat quietly with some loose-leaf paper and a pen and attempted to write out 100 dreams we each personally have. This exercise really stretches you and makes you think. Luckily, my mentor gave us an outline to help us come up with ideas. The suggestions she gave us are here:
- Experiences
- Money/Savings
- Travel
- Giving/Donations
- Family
- Influence (how to better the lives of others in a positive way)
- Material Items
We sat there for probably a good 40 minutes writing down any dream, big or small, that we could come up with. I was able to come up with 54 dreams in that time and Scott was able to come up with 32. After we called time, we each read our list to the other person and starred some of the dreams we had in common. We also stole ideas from one another that we liked and added them to our own list. This led to a very long and amazing conversation about which dreams we wanted to prioritize for this year. We also talked about dreams that might not happen for 15 years (Example: retirement) but we were able to discuss little things we should start doing now to make the future dream a reality. This exercise led perfectly into our next step of the retreat.
the Big a$$ calendar
Before our weekend away we purchased something called, The Big A$$ Calendar, along with multi-colored 2×1 Post-It notes (I will explain the need for the Post-its in a bit). The calendar is something we learned about from following the inventor of it, Jesse Itzler, on Instagram. (If you don’t know who Jesse Itzler is, I highly recommend following him on social media or checking out his YouTube page! I have learned so much from him. Jesse is a businessman, a husband, a father, an inspirational speaker, an athlete, a health advocate, a rapper and so much more.) But back to the calendar…
The Big A$$ Calendar is unlike any I have ever seen in my life. First of all, it is HUGE which is why it has the name it does. On one side it has all the months listed so it mirrors a regular calendar, but the other side is where the real magic happens. It allows you to see the entire year in one giant calendar. Each day has a 2×1 space available, hence the Post-It notes I mentioned earlier. What is exciting about this is it allows you to look at your year ahead and truly plan your whole year. Jesse talks a lot about how if you don’t put something on your calendar it likely won’t happen—which for me is so true.
Scott and I laid out the calendar on the floor of the hotel room and used our dream list to add experiences, trips, deadlines, projects, goals, and more to our calendar. We assigned colored Post-its to categories and wrote each item on them and then placed them on the calendar. Using Post-its allows us to make changes as needed and also quickly tells us where to look for a certain category because of the colors used. It helped us prioritize not only our dreams but also the projects we have been putting off. They are now on the calendar with a deadline that we agreed upon so we can hold ourselves accountable to get them done. Ideas for categories are:
- Trips
- Experiences (Concerts, events, activities)
- Goals
- Projects
- Special Birthdays
Once we got home we were not sure where we would hang the calendar but we finally decided to hang it in our exercise area in our basement. When we are done working out we can check it to see what deadlines or fun things are coming up. It has already worked great because I finally cleaned the kid’s small craft room out and turned it into a gift wrap area—a project I have been procrastinating on for 6 months! Because it was on the Big A$$ Calendar with a deadline, I got it done.
The price for the calendar is $99.00, which I know seems pricey for a calendar but hear me out. This calendar is high quality, it comes with a flow code where each week you can scan it with your phone and receive a new inspirational message, and it allows you to plan and see your life for a year on one page! What other calendar helps you do that? Most importantly, I view it as an investment in us—not just a calendar. If you would like to purchase a Big A$$ Calendar you can find them here. https://www.buildyourliferesume.com/big-a-calendar

Our calendar, minus a few post-its we took off for privacy purposes, but you get the idea!
The questions
This part is really fun and simple! We simply read the questions one by one to one another. We each have a turn to answer the question and inevitably great conversations are sparked. Each year I learn something new about Scott and something new about me, which is unbelievable because we have been together since 1985.
The questions listed below are our updated version of the original questions we were given. We found the original list to be repetitive in parts and we also came up with questions of our own that we wanted to add. Use our list as a jumping-off point but obviously feel free to make the list your own too! Here is a PDF version of the questions for you to print off!
I hope you take the time to invest in your marriage by incorporating your own Couple’s Retreat! Even if a weekend away is not in the cards for you, put aside a Saturday at home to do nothing else but focus on one another and the exercises in this post. Overall, my wish is that our version of the Couple’s Retreat has inspired you to take some sort of action. And even though it is already February you can still do it for this year. Who cares that you didn’t have the opportunity to do it right away in January. The first two years we did it, we did it in February because that is what worked for our schedule. Just make it happen at some point. That is the most important thing. You are worth it and so is your marriage!
XO- Kerry
P.S.- This year when we got back I decided to make a Couple’s Retreat Binder for us. In it, I am keeping our 100 Dreams Lists from here on out (we will do a new one every year), and also a copy of the retreat questions. I am thinking it will be a nice keepsake for us to one day look back on and see how our dreams have changed and which ones we have accomplished! Also…will we ever be able to come up with all 100?
Kerry – this may be my favorite Her Heart Stirs post yet! I share your passion for investing in my marriage. It’s a gift from God and the most important earthly relationship I have! That said, I appreciated you sharing about your mini-retreat and how your discussions about dreams, your calendar and other questions made it special. Matt and I look forward to incorporating some of the Couple’s Retreat Questions on an upcoming vacation. Thank you in advance for blessing us!