A soft sun was beaming in through the windows of Vinegar Hill House, a très Brooklyn restaurant. I was sipping a Bloody Mary with extra olives at the bar. It was a pretty springtime morning, and my parents were babysitting Hazy so that I could go on a first date. When the café’s front door squeaked open, I swiveled my head around to see who it was, and the sun was so blinding I had to squint to make sure the silhouette was the man I’d been waiting for.
He was indeed the man I’d been waiting for. And he was walking toward me.
“Hey!” I said, rising up from the barstool, not shaking his hand, which would have been the appropriate thing to do, but instinctively hugging him hello. “I’m Alyssa. Good to meet you.”
“Sam,” he said, hugging me back, not reluctantly, with a soft, deep voice. He was both sexier and taller than I had imagined—which in the world of online dating happens approximately never.
When Hazel was six months old, I joined Tinder, spontaneously creating a profile that read Single Mom in a very uncomplicated situation. (In other words: no ex-husband or baby daddy drama.) The first guy I met was obsessed with Jesus, the next with cunnilingus. Neither impressed me much. But Sam. Even his name breathed ease.
He pulled up a barstool next to me like he was out of a Western and not a row house in Greenpoint, then politely nodded to the bartender. “I’ll have what she’s having.” He was wearing a vintage Johnny Cash T-shirt that I knew was all beat-up not because he paid for the distressed look but because he’d probably had the thing since high school and worn it ten thousand times before that day. That was so much hotter to me than some Theory men’s top, not that this scrappy documentary filmmaker dude would know what Theory was.
“Should we get some food, too?” he asked. Passionate. Generous. Hungry. His pale blue eyes were strikingly kind and he smelled like a bar of plain white soap and maybe half a cigarette. Normally, the answer would be no. When you’re a single working mother, you must be a meticulous custodian of your own time, so I never agreed to meet anyone for more than one drink, not even my best friends. But bending the rules to get to know Sam seemed worth it. And whatever, I wanted to stay for a while. He was calm and I was kooky and the alchemy was there.
We ordered the lemon pancakes, the restaurant’s famous fried potatoes, and another round of Bloody Marys, with the works. He, too, loved an olive.
Then came the requisite first date small talk, which was not tedious in this case but quite lovely. I learned that Sam took the bus to our date. Gritty. He went to a very good college that typically attracted ski bums and trust fund babies. Interesting. And his favorite food was a blueberry cake that his maternal grandmother, Minnie, always made for him on his birthday. Sweet. He learned that my parents, who now officially went by “Dodo” (my mother) and “Baba” (my father), lived on the same floor as me, in a building right down the block in DUMBO. We talked about our siblings, who were our best friends, and when he spoke of his family, I could tell he was a man who was not afraid of togetherness or closeness, and that compounded with the fact that he looked like a six-foot-tall and free-of-meth Jesse Pinkman seriously got me going.
Of course, I couldn’t go too long without making things awkward.
The first terrible thing I said was that, per Facebook, we had one mutual friend in common. It was a guy who I grew up with in Longmeadow and who I once “blew in the Unitarian church parking lot.” To that little nugget, Sam nodded politely, informing me that this person was not just a random acquaintance but a close friend. “Well, don’t feel weird about it or anything. It was a pretty sloppy hookup,” I elaborated, as if Sam wanted to keep this particular thread going for one second longer.
Believe it or not, the next thing I said was arguably worse.
“So, you got a thing for single moms, huh?”
I mean, what is wrong with me?! I thought: How about next I tell him that Nordstrom Rack officially broke up with me because I returned over 90 percent of my purchases last year? No, seriously. I got a letter from Nordstrom’s corporate office saying they were “ending our relationship.” And I’d actually been really sad about it lately. Oh. I know.
Maybe I should tell Sam that I always know I’m getting a cold when there’s a canker sore on my tongue.
Or that I’m a 24-7 bathrobe person.
That I used to have great legs but I have no idea what happened to them?
Wait, is he interested in functional constipation?
What about my teenage trip to Auschwitz?
Sam—as refined as a crescent moon—teetered between charmed and stunned by the single mom question. Charmed and Stunned being his new baseline for all things with me, moving forward. We had already messaged each other a little bit online, so he knew I had a baby, and he knew I’d used an anonymous sperm donor to make her, but he didn’t know any other details. And it was in his wonderful response that I knew, conclusively, I not only wanted him but I liked him:
“I think you’re the first one. But yeah, I’m down. I’m totally down.”
Suddenly our barstools were positioned closer beside each other. We kept chatting. Sam was not a guy who liked to talk about himself very much, but luckily I was skilled at asking personal questions. Mostly, I was intrigued by his family. They were all Mainers. Coastal Maine. Rural Maine. Simple Maine. Farming Maine. Fancy Maine. He said his dad bought a dilapidated shack, in a town called Verona Island, back in the early eighties, and as he painstakingly built the family something more sustainable, they all slept on mattresses in the hallways and everyone used an outhouse. Before I could fish around for any more details, Sam led the conversation in a different direction.
Without saying it in so many words, Sam wanted to let me know that nothing about my motherhood felt fraught to him. He told me that within his closest family and friends, they’d experienced one pregnancy through surrogacy, another through egg donation, and there was an adoption in the works. Because he had sisters and sisters-in-law and lots of aunts of all ages, he was open and enlightened when it came to fertility, and that was really refreshing.
“Thanks so much for telling me all that,” I said, a smile spreading across my face like butterfly wings. It wasn’t like I needed a guy to tell me he was okay with my choices, but I also didn’t realize how comforting it would feel to hear it.
From This Might Be Too Personal by Alyssa Shelasky. Copyright © 2022 by the author and reprinted by permission of St. Martin’s Publishing Group.

This Might Be Too Personal is available from Amazon and Bookshop.
