What if your goal was to run a marathon? You signed up. Got your number. Put your toe on the starting line. Ran a dozen or so miles. And then it got hard. Real hard. And you didn’t make it to the finish line.
You said you were going to complete a marathon. And then you failed.
A few years later, you still want to run a marathon. You even get a number again. But now you are afraid; you have already failed once. So, this time, you train. Hard. Every day. You put in the time and the work. You make it a priority.
I found myself in my late fifties, post-failed marriage marathon, and edging into loneliness when I reluctantly volunteered for the tough-mudder obstacle course, otherwise known as online dating. Surprisingly, I gruelled through the course, in the end, standing on the winner’s dais next to a guy we’ll call Grey. My new running partner?
On our first date, we kayaked down the Chestatee River. We stopped at a patch where the bank of the river became a beach, and many folks before us had apparently stopped as well, as the small beach was populated with stacked stone miniature monuments. A crowd-sourced work of public-generated art.
We climbed out of our kayaks, and like so many before us, Grey began to build a tiny stone structure. After collecting a few rocks myself, I began to stack mine too. What if I could stack an elegant pile of stones next to an existing pile, and somehow, toward the top, the two became one, like an arch? I would build a secret monument to our first meeting in person, an expression of hope and vulnerability. I stacked my rocks close to an existing stack and every time I placed a long, skinny rock on top to connect the two stacks, both stacks toppled over.
As we worked to craft our mini-sculptures, we talked. Tell me a secret, I asked. And he did.
When you begin a new relationship after a failed long-term marriage, you ask different questions, you stack your stones differently, you look more closely and more carefully at what is swimming beneath the surface and at how he communicates it.
After our second date, we needed a plan. Grey and I lived on opposite sides of Atlanta, over an hour apart. Picking me up for dates and dropping me back home with an hour’s drive ahead of him late at night was not a reasonable go-forward plan. What if we considered this a long-distance relationship, and he came into town and stayed with me? We planned out the next three weekends. “After that,” I suggested, “We can evaluate the situation.”
Although it had been some time since I experienced the pain and disruption of my ex-husband closing the door on what had been our life together, I was fearful. I feared making a mistake, letting my heart get ahead of Grey’s, or his heart getting ahead of mine. I feared every outcome, especially things going so well between us, that his expectations exceeded my readiness.
After three weeks, we sat outside under a pergola, holding hands. Time to evaluate. Should we go forward? If so, how?
Early in a relationship, a conversation about the future can be a dance of sorts. He took the lead. We are, he said, independent adults with our own lives, but we were going to be a couple and be exclusive. I loved what he said. I loved that he wanted me to feel safe and important, things that he knew I wanted because he had listened carefully to me over the past weeks. I listened, took a shaky breath, and responded, “I can be all in,” I said and hastily added, “For three months. And then we can evaluate again.”
And that’s what we did. Every three months, from then on, we had what we came to call Eval Weekends.
For the first twelve months or so, the weekends really did kick off with a Friday night conversation and agreement to keep moving forward. Saturday and Sunday, we focused on getting to know each other on a deeper level, sharing expectations, talking through fears, and bringing up touchy subjects. Training. Hard. Now that we have another race number, we don’t want to quit or fail. We want to make it to the end. In other words, doing the real relationship-strengthening work while at the same time creating joyful and memorable experiences.
Pausing here to say yes, we really do this, and also to say that I know it’s not normal.
Every three months, my boyfriend, aka Grey HingePin, and I devote a full weekend to each other and to our relationship; we focus entirely on ways to know each other better; how can we get to the next level of loving each other? We examine our own lives and our lives together from every angle with courage. How can we find issues and head off resentments?
Are these weekends tough sometimes? Sure. Are they amazing? Always. Are we crazy? Maybe. Though you could argue that embarking on a committed relationship in the wake of the failure of your previous twenty-year-plus relationships without actively working to learn and change from the experience is probably crazier.
I love to share the Eval concept with people, and I typically end up fielding a few questions.
The first question (always): How does your boyfriend feel about Eval Weekends?
He hates Eval Weekends, of course! Or at least he loves to act like he hates them when he knows one is coming up. It’s part of the fun.
I can understand why everyone asks that question. Evaluating the relationship sounds scary. I’m glad we overcame that fear. After almost five years, we would both say our Eval Weekends are the key, the best part of our relationship. Like Babe Ruth said, ‘Never let the fear of striking out get in your way.’
If you step up to the plate, who knows, you might hit a homer.
Now, on to the other frequently asked questions.
Next Question (typically): What in the world is an Eval Weekend?
Since I have already kicked off a baseball analogy, why not keep it going? Below is our basic lineup.
Example: Eval Weekend Basic Lineup
As you can see from the lineup, we usually include a couple of deep work blocks. Setting some time aside for what we call ‘deep work’ is essential. This is the time to do the actual work to build and strengthen your relationship, batting practice. More about this later.
The deep work blocks are just part of the secret. What is important is spending as much time as possible with 100% attention on each other, often doing an activity together we normally wouldn’t do.
As a guide, a solid Eval Weekend is a combo of deep work and meaningful conversations, goofy activities and memorable experiences, creativity and romance that you have prioritized and planned together.
The Official Guide: The Eval Diamond
For our Eval Weekends, we look to cover all the bases of the Eval Diamond, and I share more about each below. That said, it’s just a guide. We keep it flexible.
The Eval Diamond
First Base: Planning it Together is the Single Most Important Element
The most essential ingredient in making the Eval Weekend special is that each of us contributes to the planning and prep. Even a small amount of forethought and planning as to ‘how’ to invest the time adds to the effectiveness of the Eval. Simply taking the time to share ideas about the upcoming Eval elevates the experience.
One approach we use is to divvy up the planning into chunks; we take turns, volunteering to plan and provision portions of the weekend. He might offer to prep and plan for Friday night, Saturday afternoon and evening, with me stepping up to take on planning for Saturday morning and Sunday morning.
As the upcoming Eval Weekend approaches, it’s crazy how much it means to me when Grey brings ideas and suggestions. When he invests time in planning and getting ready for the weekend, it shows me that our relationship is important to him. I go into the weekend so grateful for what an amazing team player he is.
Second Base: Double Down on Creativity and Romance
You may be thinking an Eval Weekend sounds uncomfortable enough, but having to plan it together is even more concerning – and now you want me to bring in creativity and romance! I’d rather speak in public!
I get it, and for those uncomfortable with speaking in public, Dale Carnegie provided a great suggestion, a framework for planning a presentation that helps ease the anxiety over whether or not it will be a good presentation. Carnegie suggests that a speaker should always give the audience “Something to feel, something to remember, and something to do after the presentation.”
So, as you’re thinking of your upcoming Eval Weekend, you can use Carnegie’s ideas to provide a framework as you plan.
For instance, when it comes to coming up with ‘something to feel,’ I might want us to come away from the weekend feeling hopeful. So, suppose I had volunteered to plan Saturday night. In that case, I might plan an after-dinner activity where we go out in our backyard, roll out a blanket, lay on our backs, and look at the stars, holding hands, taking three deep, wonderful breaths. Then, we each make three wishes. And when we know what our wishes are, squeeze the other person’s hand three times (I – Love – You). I would typically add some structure here to make it easier: One wish for myself, one wish for my partner, and one wish for us as a couple. Or I might suggest a start, stop, continue version as in ‘what is one thing you wish we would stop, one thing you wish we would start, and one thing you wish we would continue.’
That activity would potentially give Grey and me something to feel, remember, and do. And it would be a creative way to bring romance to the weekend.
Third Base: There’s Nothing Better than the Triple Play – Distinctive, Goofy & Memorable
While the time we spend on Deep Work will always be most important, how we spend the remainder of the weekend matters too.
Even though our weekends were more serious at first, we had histories, triggers, and icebergs to talk through and look under – feelings and fears to share — we would always incorporate playfulness and activities that were slightly out of the ordinary for us. The best weekends are fun, goofy, and memorable. So we might plan something normal, like going for a hike, but then choose to make it more memorable by going at sunrise or dial up the goofiness by adding a unique twist to the venture: Every time we see a beautiful view, if there are no other people around, we will stop and kiss.
One time, we were hiking on a segment of the Appalachian Trail, something I had never done before and always wanted to do(!), and as we stopped to take in the view, Grey took me in his arms and sweetly kissed me. We heard a woman farther down the mountain say, “See! If they can kiss, we can too!” and when we caught up with them a few minutes later, we had the best laugh together.
Lately, we started coming up with themes for Eval Weekend. One weekend, we knew the weather would be amazing, and we wanted to spend as much time as possible being active; before we knew it, we themed the weekend’ SPORTS!’ and even ordered t-shirts that said ‘SPORTS!’. With SPORTS! in mind, Grey surprised me with a Friday night picnic at a nearby park, including delicious ballpark hot dogs, plus all the equipment we needed for a badminton tournament and a follow-on game of catch, including (I couldn’t believe it) baseball gloves he had purchased.
Saturday night, we decided to have dinner at a local sports bar. Over dinner, sitting at the bar, we would acknowledge how amazingly the other had performed over the last three months by bestowing sports-themed awards on each other. Some of the awards I gave Grey were Best Team Player, Offensive Play of the Year, Defensive Play of the Year, Home Run Derby Winner, Coach of the Year, and Best End Zone Dance.
Grey had the idea to dig up a bunch of old participation trophies that we could bring and stack in front of each other at the bar. That visual always makes me laugh at how goofy that would have been. Each of us with a cache of previously-used little league, cheerleading, and soccer trophies in a bag hanging on the back of our chairs, pulling them out, presenting them, and setting them in front of each other.
The activities we plan together are not always goofy. Eval Weekends are also about investing in our best selves, so since having healthy habits that make us stronger physically and mentally is important to both of us, we make sure our Eval Weekends incorporate exercising and meditating together, too. In other words, Eval Weekends reinforce our commitment not just to our best relationship, but to our best selves.
The idea is to make it distinctive with goofy, fun, unusual, or affirming activities you think your mate will enjoy – you may not hit it. Still, you planned it; you brought something to the table. There is a vulnerability in planning surprises for each other, being goofy together, and a bond that forms between us when we try something new together.
The Stretch: Deep Work
We love to plan activities like doing a YouTube yoga class, watching a Master Class on negotiation, playing a board game, trying our hand at reading Tarot cards, or maybe making a batch of homemade Limoncello.
At the same time, we set aside time, ideally at least three to four hours spread out over the weekend for learning and sharing.
Most importantly, Eval Weekends are a prime opportunity to focus one hundred percent of our attention on each other and build the best possible relationship. Committing to the effort.
It’s like saying to yourself, only I can make sure my body gets stronger, making the decision to commit, walking into the gym, putting my hands on the weights, and then stepping forward with the weights in my hands and bearing the weight. It just makes me stronger.
Likewise, an Eval Weekend is weight training for our relationship. If we are not lifting the weights and getting stronger, then what? I know the answer to that question already.
This time is all about heart-to-heart communication. We come up with interesting ways to interact – how can we get to the next level of really knowing and loving each other? Let’s say we have the idea of taking a personality test together, like Love Languages. As part of the advance prep, I offer to come up with a few prompts or questions around Love Languages that would give us ideas for conversations we have not had before.
Example: Deep Work Prompts
I just made up that set of exercises given the Love Language prompt. It took me about ten minutes to jot down a framework and another ten or fifteen minutes to write out a short guide as I thought the concept through.
The time we spend on deep work is to examine ourselves and our relationship from different angles. Sometimes, we reflect on issues or parts of our relationship we need to face head-on. However, one of the most interesting and unexpected outcomes of prioritizing regular Eval Weekends is how often we now address issues proactively because the Eval Weekend is coming up. Why ruin a perfectly good Eval with tough stuff if we can address it now? The focus is really on a better relationship through learning and experiencing together, not just fears and obstacles but achievements, gratitude, hopes, and dreams.
The Love Languages prompts above are just one example of a topic to explore. What would work for you?
Bringing it Home
By now, you are probably thinking, even if I could get my partner to agree, who has the time for this? Work, children, and chores take up all our time.
So maybe you have an Eval night or an Eval Saturday. Our favorite approach is an entire weekend, just the two of us at my family’s lake house. However, now Grey has a career that requires him to work every Saturday. We still have Eval ’Weekends,’ we just don’t get a whole Saturday and Sunday together like we used to. Yet, the Eval Weekends are more valuable than ever. We are still doing the work, lifting the weights. Committed to being strong.
Eval Weekends started because I was afraid; afraid of committing to a relationship when I didn’t have a way of knowing if it was right for me.
Remember the stones? When, on our first date, Grey and I got out of our kayaks and started to build our own little stone sculptures. How I wanted to stack my stones next to another sculpture and place a stone on top of them, like an arch, to connect them. That day, when Grey finished his stack he came over next to me, and I admitted what I was trying to do, that I wanted to use a stone to connect the two stacks, but every time I tried, they tumbled over. “Let’s try this,” he offered and he knelt down, picked up two thin, flat stones, and balanced a single stone at the top of each stack; the two top stones ouching, connecting.
Eval Weekends helped us understand and get through our fears and build on our hopes. Our hope for a better, stronger relationship prompted us to continue building sculptures we call Eval Weekends, where we genuinely connect while also providing us the opportunity to stop and notice the beautiful view right there in front of us.
What are you afraid of? What do you hope? What could you build?
Example: Sample Eval Weekend Plan
Orange Door Hinge 
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