An Adventure into 26
Sara Rayfield talks about dating a younger man and how life doesn’t always bend to your changing plans.
When I started dating again after my divorce, I wasn’t really sure what to expect. A single mom in my mid-30s, well-educated and entirely self-sufficient, I had no idea if dating was going to be easy, entertaining, weird, complicated. …
It turns out, it’s all of that.
I did that online dating thing for a few months. People who know me are oh-so-shocked to discover that I lack the patience for the pitfalls of online dating — the questions of did I use the right picture and is this person probably a serial killer were just too overwhelming, so I stopped.
I did meet an older man — and it was fun. But like most things in life — my marriage and a recent election spring to mind — it didn’t work out, so I tied up those heartstrings and decided to climb in a car with some friends for an adventure.
If only I’d known where that decision would lead.
Standing in the kitchen of my best friend’s house, we waited for our friends to arrive. This Saturday night was particularly painful because it had been scheduled for something else, with someone else. But distractions are a sad woman’s best friend, and I accepted the invitation for a road trip to Quincy, Illinois, for a roller-derby bout. My friend had retired from the sport a few years earlier after breaking her leg in two places, but her roommate and most of our friends were still active players. Carly and I were older and mothers, so as we made new friends, we adopted them into our family.
Once Beth, Renee, and Chris arrived, we set off in the car. Carly navigated in the passenger seat while Renee drove, and Beth, Chris, and I squished into the back. Somewhere around Hannibal, the mocking started. Chris, the youngest of our group, did something gross, juvenile, and smelly with his young-person plug earrings. I handed him a moist towelette from the bottom of my purse as he looked at me wide-eyed.
“Dude, I’m a mom. Of course I have wet wipes. I have some suckers, too, young man.”
We hit it off quickly, despite our 10-year age gap. Apparently older women are his thing, and apparently being a single woman is not my thing. We joked around for the remainder of the evening. At the after-party at the bar, he tried to buy me a beer. I say tried because he wasn’t carrying any cash, and I saw the fear in his eyes about the ATM charge at this bar that wouldn’t accept his credit card. Enjoying any chance to flip the script, I pulled out a wad of cash and bought him a PBR — because of course — and a Bud Light for myself.
In the car on the long drive back to St. Louis, he sat on one side of the car and I sat on the other, with Beth asleep in between us. With all the confidence in the world, he reached his arm across the back seat and started playing with my long, blond hair. We made eye contact — and I just shook my head at him, laughing. What in the world, I thought.
We started texting the following week, and he asked me out shortly after. I said no at first, because while flirting is fun, I had found dating to be anything but. And then he asked me out again, until I said yes.
Here’s the thing. You don’t get a guide on how to date after divorce — although I’m sure they exist and I could probably have one with free shipping through Amazon Prime. So, like everything else I do, I dove in with my whole heart. Our first date was more fun than I could have imagined — Thai food, delicious cold beer, skee-ball, and people-watching. After a few drinks, we went back to his place, where I forced him to watch my favorite Broadway musical, Newsies, and then stated matter-of-factly, “You know we aren’t going to have sex tonight, right?”
He looked at me the same way he did when I thrust a wet wipe into his hand, somewhere between St. Louis and Quincy. A little amused, a little uncertain, but fully interested. Halfway through the reprise to “Seize the Day,” he forced me to stop my mini-singalong by kissing me.
Turns out that “we aren’t going to have sex” were famous last words.
Later in the evening, we cuddled close to each other, absorbing each other and discussing our various tattoos and scars. I got up to leave, not knowing what to expect from my tryst with a millennial.
“Do you want to borrow a pair of sweatpants to sleep in?” he asked.
You have totally done this before, kid, I laughed to myself. Light years past my comfort zone already, I had no idea where this was headed. I put on the heather-gray sweats that he placed into my arms while he took out the dog, and then we drifted off to sleep.
Our next dates alternated between our age ranges — we spent evenings bingeing Netflix and window-shopping. We spent his birthday weekend at Oktoberfest, where we had sex in a parked car, and he held my hair back while I threw up from one beer too many. We welcomed his 26th year together; we attended weddings and brunches and poetry readings. It was never boring, although it was exhausting. Twenty-six is a turning point for most people, trapped between student-loan debt and entry-level jobs and roommates in order to get by on a budget. Holidays started passing us — Halloween, Thanksgiving, and Christmas. We celebrated my 36th birthday together, holding hands in a Winter Wonderland filled with Christmas lights and red roses.
It started as an adventure, but around New Year, it turned into more. We had been fairly private about our relationship until then, but as the midnight turned our life into a new year, we opened up. I met his mom, and he got to know my child. We shared a Netflix account, and I helped with his résumé. Conversations would occasionally cross into more serious discussions about the future — a stark contrast from my earlier refusal to plan for anything more than a month in advance. He kept me young and wild, and I helped him grow into his age.
I woke up one morning next to him and discovered I had accidentally fallen in love. With a 26-year old. With someone who didn’t know what song I was singing when I talked about the song I was named after — “Sara” by Fleetwood Mac. Someone who was EIGHT when I graduated from high school — who was graduating from high school when I was at my 10-year reunion. We had learned how to deflect the inquiring looks, questions, and comments we received when we went out together. Most people thought our age difference was amusing, but more than anything, we just didn’t care. Although the differences were often apparent, more often than not, they were exciting. We each had our hurts and scars and strengths and skills, and we pushed through it, because we held each other’s hearts at the same time.
For almost ten months, we were each other’s cheerleaders. We got new jobs, discussed insurance plans, shared house keys. But as I fell more in love with him, I opened a rift. I knew what I wanted. I know, in general, where I am headed. I steer my ship the way I always have, with the stubbornness of a woman who has gone through a divorce and a custody battle. Chris — well, he lives with the naïveté of someone who claims to have only been in love once. The realization for both of us that my feelings were deeper than his was like a lightning bolt between us. I put away the plans I had made, now scared by his own uncertainty. On his behalf, he tried his hardest to play catch-up with me — but how can you? How do you make up for ten years of extra experience?
We broke up on a Monday. We both wept as we sat on my bed, realizing that we were unraveling something we had spent hours, days, months building. Despite our age difference, he handled our separation far better than I did. He called his mom while I called him asking to stop what we accidentally set in motion. My heart was aching with emptiness. We spoke the next day and agreed to see each other the following Friday.
As I sat on his bed one last time, it was obvious neither of us knew what to do. We looked at each other and laughed. “I feel like this is our first date all over again,” I whispered. He pulled me in and kissed me, the same way he always had. The way he had on our first date standing on a bustling city street, our second date nestled on Carly’s couch, on my birthday under Christmas lights, and on New Year’s surrounded by friends. We had discussed how we wanted one final night together — wrapped in each other in the familiar way that old lovers know.
“Why can’t it always be like this? This is what we want.” I whispered into the soft space between his shoulder and chin. Our bodies knew each other; even the simplest touches created intimacy.
“It’s because we know it’s the last time,” he sighed back. He stroked my hair with the same tenderness he had for months. I rested my hand on his arm and could feel the goosebumps on his skin — one last physical sign at our emotional connection.
Dating Chris at 26 was something entirely unexpected. He made me wild, carefree, immature, and reckless. The last thing I loved — a love and loss that will remain with me in the memories of his hand on my hand, his heart in my heart.
