Love in Midlife Is Extraordinary. It Is Also a Lot.
On finding your person after you've already found yourself — and what it actually takes to build a life together.
I don't talk much about finding love the second time around, though I did share my recent wedding with you here. What I haven't shared is what came before, and what has quietly surprised me since.
Before I met Andy, I had ten glorious years of being single. I use the word glorious with full intention, because those were the years I came home to myself. In that decade, I moved three times, after spending 45 years in the same place. I learned to let go of possessions, relationships, jobs, alcohol, and ways of being that had long since stopped working. I ultimately learned to let go of what I thought my life was supposed to be.
Every single time I let go, there was a cycle. First came fear and grief, real and powerful, the kind that throws you off balance. Then came possibility, a small and stubborn light that asked: what could be on the other side of this? Then came the adrenaline of one step, one decision, one day at a time. And then, eventually, something I didn't expect: courage. confidence. A resilience I had quietly built without noticing. Every letting go had sweetness and sorrow braided together.
By the time I landed in Colorado, I had built a life I loved. Real rituals, real friendships, real spaciousness. A relationship with aloneness that was nothing like loneliness. It was freedom. It was mine.
And then I met Andy.
I knew pretty quickly that he was my person, the man I wanted to explore forever with. And yet. Love in midlife is extraordinary, and it is also a lot.
We came to each other with careers and homes and aspirations, with two children each and ex-spouses and four living parents between us, all somewhere between 85 and 95. We each arrived with our own financial realities, our own estates and the people inside them, our own visions for retirement and legacy. Not to mention the rituals and habits and idiosyncrasies that had become the architecture of who we each are.
So while we were doing all the things new love does, spending time together skiing and hiking and going to concerts and beginning to imagine a shared life, we were also having the other conversations. The ones that took more courage than any of the fun parts.
Financial disclosure, which for me surfaced real discomfort and old shame around my own money story. Building a shared budget when our financial realities are different, which was vulnerable and exposing in a way I hadn't anticipated. Navigating a prenup, which I'll be honest, felt deeply uncomfortable at first, and which ultimately left us both feeling more connected and more safe than before we had the conversation. Estate planning together, which meant sitting with every possible future, including the ones we didn't want to imagine. Getting clear on how we would show up parentally, individually and together.
None of these conversations were easy.
All of them were worth it.
What I keep coming back to is this: the heat of new love is extraordinary. And what has been even more extraordinary is being asked, at 59, to walk my talk.
I love my relationship with aloneness. I love Andy.
How those two things coexist is a daily practice, not a problem to solve. It is one honest conversation at a time. It is spoken truth, and choosing to show up for each other, and compromise that doesn't ask either of us to lose sight of who we are.
It is the continuous work of figuring out what belonging looks like when you have already learned to belong to yourself.
I don't have a tidy ending for you here, because there isn't one. We are in it, the beautiful and complicated and occasionally maddening work of building a life together. What I know is that I would not trade any of the years of aloneness, because without them I would not have known how to do this. And I would not trade this, because he is worth every difficult conversation we have had and every one that is still coming.
If You Are Newly in Love in Midlife
Have the money conversation early, and have it fully. Not just income, but debt, spending patterns, financial fears, the money story you carry from your past. It is uncomfortable. It is also the foundation. You cannot build a shared life on financial secrets or assumptions.
Get clear on your non-negotiables before you need them. Your time with your children, your relationship with your own solitude, the habits and practices that keep you sane, the things you are not willing to give up. Not as a defensive list, but as an honest one. A partner worth having will want to know. And knowing your own edges makes you far easier to love.
Do the legal work, together. The estate planning, the prenup conversations if relevant, the decisions about what happens in the futures you don't want to imagine. I know. It sounds wildly unromantic. What it actually is, is one of the most intimate things Andy and I have done. Facing every possible future together, including the hard ones, made us feel like a real team in a way that hiking and dinners and falling in love did not.
Stay in the practice of being alone. Don't let love collapse the life you built. Your solitude, your friendships, your rituals, your self, these are not things to sacrifice at the altar of partnership. They are what you are bringing to it. Protect them. A relationship that requires you to disappear is not the right one.
This is part of my unfolding that I didn't see coming. Not the end of the story I built alone, but the next chapter of it, written by two people who already knew how to stand on their own.
