Being single in my 40s has led me to places I could’ve never imagined—including marrying myself at the biggest theater festival in the world.
Calling off an engagement to the wrong person is tremendously relieving. It’s finally finding a women’s toilet after being stuck on Berlin’s U-Bahn for an hour, then tearing through the station, helplessly mewing, “Wo ist die WC?” to anyone who will listen relieving. It’s 500 thread count satin sheets, room darkening blinds, and no alarm set after a harrowing day at work relieving. It’s some shade and an Aperol spritz on a hot day; it’s that business trip you were dreading going on getting cancelled at the last minute.
It’s also, if we’re being totally honest here, deeply embarrassing.
Chapter 1: The Princess Saves Herself in This One
People seem to understand the gravity of things like death and divorce. A broken engagement? I got the stupidest comments.
“Will you get to keep the engagement gifts?” Why would we?
“Too bad, I was really looking forward to that party.” So was I, deal with it.
“But you were such a cute couple!” Thanks, I was dying inside.
And my personal favorite, “For the sake of our social group, we’re not taking sides and we hope you will still show up at parties together.” I’m so heartbroken I can barely get out of bed in the morning, but it’s great to know that the ratio at brunch is the most important thing to you.
The worst part was people feeling sorry for me. As a woman in her early 30s, I’d outrageously flunked the find a man and get him to the altar ASAP test that somehow even my most feminist friends seemed to be embracing and acing.
How did I manage to finish last in a race I didn’t even know I was running? And what was my life going to look like now that the American cookie-cutter dream was no longer in my near future? Did I even want that anymore? What was wrong with me that I didn’t want that anymore?
Some days flunking the marriage test felt like having a contagious disease, one that other women were distancing themselves from me to avoid catching. For some, I was a reminder that perhaps their safe little lives weren’t as locked down as they’d like them to be. After all, if it could happen to me, it could happen to anyone.
Above all, people wanted answers. Why did this seemingly perfect couple break up four months before the wedding?
Did I owe people answers? Did I have to put my pain on display to deserve empathy? Was I supposed to explain how exhausting it was to come home night after night to a relationship where neither of us felt like we knew each other anymore? Where we lived in separate orbits, carefully giving each other space while maintaining the illusion that we were happy for everyone on the outside.
Thankfully, some people understood the assignment.
The divorced friend who showed up at my home with wine and tarot cards to sage the space after he moved out. The cousin I barely knew who sent me a message saying, “That was brave. Most people wouldn’t have the guts to call things off after they set a date.”
I will remember the people that reached out forever, and I’ll also remember the silence from people who I thought really cared.
Chapter 2: Starting Over is Punk AF
There’s a corny old saying that the cost of the life you dream of is the destruction of your old life, and for me that is absolutely true.
A broken engagement in your early 30s will call into question everything you thought you knew about yourself and the life you thought you were supposed to be living. It will force you to bury the version of your life that was on schedule, where everything was going as planned. It will make you feel like a failure, like you’ve let down your family and your community. Like you’ve let down yourself.
It will also teach you life lessons that many women don’t get to learn until they’re in their 40s or 50s, and for that I’m incredibly grateful.
For me the most important of those lessons was decentering romantic love and not waiting to “find someone” to start living the life I wanted. For a lot of women, these revelations don’t come until years of marriage and kids, years of self abandonment, years of silencing the little voice inside us telling us that it’s OK to want more.
I didn’t have it all figured out in the months after my engagement fell apart, but I did have a gut feeling that I’d been handed a second chance at life and I wasn’t about to waste it.
What did that look like for me?
Getting a job abroad in Switzerland, letting go of the life I’d spent over a decade building in Boston, packing what was left of it into two suitcases and moving to Europe.
Extreme? Maybe. But it was hands down to this day, the best decision I have ever made.
RELATED: All the Cool Girls Are Single in Their 40s
Chapter 3: Emily in Paris Lied to Us
Picture yourself as a newly single woman who has just moved to Europe. What do you see? Sipping a cool glass of white wine on a sun drenched terrazzo? Effortless weight loss from eating European bread and strolling across cobblestones in your newly purchased vintage Prada mules? Dates that begin on the back of a moped with Sergio (who smells fantastic by the way), and end with the two of you kissing passionately in front of the Trevi Fountain?
OK, now picture crying because you can’t figure out how to use your washing machine, crying because your elderly neighbors just took you to task for not sorting your recycling properly, crying because you’ve put on a bunch of weight after being too tired and overwhelmed to exercise or cook properly, crying because instead of a moped, Sergio has three other girlfriends and a cocaine problem.
There was so much crying in my first year abroad.
But the knowledge that my life now belonged 100% to me kept me going. And in the immortal words of RuPaul, I was not going to eff it up.
Language barrier? I started taking lessons and spoke my crappy German to anyone who would listen (spoiler alert: it was mostly elderly people and little kids).
Culture clash? First I made friends with other foreigners who taught me the mysteries of Swiss recycling. Then I made Swiss friends. People will tell you that’s impossible, but the key with Swiss people is to play the long game, take off your shoes when you enter their home, and never, ever flake on kaffee und kuchen once it’s on the calendar.
Boy problems? I deleted my dating apps and focused on cultivating a girl-gang of ride or die besties. I discovered the magic of solo travel sans Sergio. I knuckled down on my career, my writing, and went back to school to get a doctorate. All of that was way more satisfying to me than an Insta-worthy Trevi Fountain snog ever could be.
The old me who thought nothing would make me happier than walking down the aisle in a white dress, surrounded by my nearest and dearest was such a confused, sweet summer child.
Absolutely nothing has made me happier than throwing away the blueprint of life I was handed, knitting my own net while I’m falling, and building a life that was meant for me. One full of friendship, purpose, creativity, and connection.
Moving abroad was without a doubt the hardest thing I’ve ever done, but it was also the best.
Chapter 4: Marrying Myself in Front of an Audience of Strangers
The thing about living your dreams is that those dreams don’t get laid to rest, they get bigger. When you do what you thought was impossible, your realm of possibilities gets even bigger.
I’ve been solo abroad for a little over a decade. Now in my 40s, I’m coming into my witchy wisdom era in a way that would leave the old me gaping.
I love my solo life. I don’t feel incomplete. I feel self-partnered.
But I do feel like I’m tired of watching my life rush by, the moments I’ve worked so hard for barreling past me like a high speed train.
I want a chance to mark my milestones and celebrate the things that society doesn’t give single people a ritual to mark.
It’s time to create my own ritual.
As a girl who makes theater, my ritual was always going to be a show. I decided to marry myself live onstage. And I decided to do it at Edinburgh Fringe, the largest theater festival on the planet.
The idea didn’t come to me all at once. I’ve been writing and doing comedy for a few years now, and inevitably, my solo life abroad has been the fodder of many a tight five at an open mic. People often come up to me after shows and say, “Girl, you’re singing my song.” Even men sometimes tell me they find my story relatable.
We all know the stereotype about the hapless, single woman. Obsessed with her career, hopeless at dating, holding on for dear life to friendships with married people who have long since moved on but feel sorry for her.
To me, none of these could be further from the truth. So I started writing. I decided that I’m going to tell my story live onstage and at the end of the 50-minute show, I will be married to myself in front of an audience of strangers.
I threw my hat into the ring for a Fringe venue. I have no director, no production team, no designer, no PR, just myself and a burning desire to tell my own story.
I got the Fringe venue.
Immediately after I received the news, I put up a social media post saying I’m doing a show at Edinburgh Fringe so I couldn’t back out of it.
I went to Edinburgh and trolled thrift stores for the perfect second hand wedding dress to commit to myself in.
There have been moments in this process when I’ve doubted myself. Is it horrendously cringe and embarrassing for a single, 40-something year old woman to put on an actual wedding dress and marry herself onstage?
Maybe. But I don’t care.
My Edinburgh Fringe show Married to Myself opens on August 8th. I’m in Edinburgh to connect with audiences who are like me. Maybe you’re solo, maybe you’re partnered, maybe you’ve had a moment in your life when you’ve felt like you’ve lost everything. Maybe you’ve had to promise yourself after a personal setback, your story doesn’t end here.
If this sounds like you, you are cordially invited to my wedding. And if you can’t make it to Edinburgh, I encourage you to make a vow to yourself in your own heart, and stop waiting around for Sergio to take you on that wild ride. You are infinitely capable of sweeping yourself off of your own feet, and I guarantee you, the scenery will be better when you’re on your own adventure.
THE ALLY O SHOW, MARRIED TO MYSELF is at Edinburgh Fringe 2026
Pizza Geeks Easter Road (venue 220)
August 8-9th: 12:10pm & 7:10pm
August 10th-15th 12:10 pm
(no show August 12th)
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by Alyssa O
Alyssa O is a writer, actor, improviser, and immigrant who has lived in Switzerland, Scotland, and Germany. Her comedic writing has made her a finalist for the BBC’s Scottish Voices Talent Development Programme and has been longlisted for Helen Lederer’s Comedy Women in Print Prize. She writes and performs for every woman who’severbeen told she’s too much. You can find her on Instagram at @alyssaowrites.
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