How I Learned Not to Date Down
I thought I could spare myself heartache by settling. I was wrong.
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It’s Sunday and I’m walking around Greenlake with Sven — not his real name, in this story nor in real life.
When we connected via Bumble, he told me his real name was Steven, but he wished to go by Sven. “Fine by me,” I told him. “I’ll call you Sven.”
At 58 years old, Sven has half a decade on me, and at first impression I could see those years mattered — both in the deep wrinkles around his eyes, as well as some Boomer-like tendencies, like his dislike of texting.
But I decided to take a chance and call him, and was pleasantly surprised; our conversation was electric, charging across topics with animated ease. “Whether we date or not, we’re definitely going to be friends,” he told me. “I want you to read my film script.”
“I’d love to, and I agree,” I enthusiastically replied.
I called my bestie Sunny Hong as soon as the call ended. “I’ve maybe connected with someone who feels like my equal!” I gushed.
This rarely happens. Most men can’t keep up. He invited me to walk around Greenlake that weekend, and while I still had apprehensions about his appearance and age, I was cautiously optimistic.
If nothing else, I felt sure I’d make a friend.
I arrive first and walk to the lake’s edge, staring at the placid water and breathing in the cool air. Then I take a selfie, my freshly dyed hair fiery against the murky skies. Whatever the day brings, I think, I want proof that I look powerful, and kind of cute, too
Now we’re strolling the 2.8 miles around Greenlake on a Sunday afternoon so overcast, we nearly have the lake to ourselves. We encounter a couple sets of baby geese, ridiculously fluffy and adorable. Halfway around, I ask if he’d mind stopping so I can order a tea to keep my hands warm. He says he doesn’t, so I do. We talk and talk. Our conversation is lively, if not as overflowing as our initial call was.
And he’s cute, sorta. He has nice eyes, and his hair, while thinning, curls around his forehead. I like his British accent, as I knew I would. Average height and build, average dresser. I’m not really one for average, and he wouldn’t catch my eye on the street. Give him a chance, I think. It’s probably better to find a guy who leads with brains instead of his looks.
I also can’t read how he feels about me. But as our footfalls find us back to the boathouse where we started, he asks, “Want to go around again?”
Okay, then. Surely he’s interested if he’s committing to another three miles of conversation, right?
As we start our second go-around, we compare online dating notes. I tell him how I find it a time suck, sorting through potential prospects and investing time in mostly futile searches. “My life runs on tight margins, with my job, writing habit, and parenting schedule,” I joke. And it’s true. I have only three nights a week without my kids, I tell him, so I’m protective of my time.
“Thanks for slotting me in,” he mumbles. His tone seems off, but it’s just a blip and the conversation moves on. Sven tells me he can enjoy meeting with anyone, so long as there’s an actual conversation. “Are we having an actual conversation?” I tease him, smiling.
“No, I’d say not really,” he answers, stone-faced.
I glance over as my smile fades. Is he serious? I ask what he means.
“I expect an actual conversation involves back and forth, with the person asking questions about me,” he answers. “And you haven’t done that.”
My brain lurches. I’m hyper-aware of my propensity to talk a lot. I’d like to think it’s one of my superpowers, but I also know I can overpower people. This is doubly so when I’m meeting someone new. I make a concerted effort to both talk and listen. Sometimes, I fail. I’m certain I said, “I’m probably talking too much” more than once as we circumnavigated the lake.
But had I talked too much? Had I failed?
We’d only just started lap two when he dropped that actual conversation bomb. Now I’m so self-conscious about needing to ask him questions, all while churning inside under the weight of his accusation, silently interrogating myself with every step.
This is all my fault.
(Is this really all my fault?)
I’m no longer having fun and my feet are blistering.
I wasn’t even sure I felt anything for this guy. But now I feel something: bruised.
A week later, I meet Sunny for a delicious late-night dinner. It was a glorious pre-solstice evening and the golden hour cast a glow on my blackberry butter salmon bowl and an icy Aperol Spritz. Pure bliss.
I’m eager to hear her thoughts about my unfortunate date with Sven, and to discuss it in the context of a broader dating phenomenon I’ve experienced but haven’t been able to explain. Sunny is as thoughtful as she is incisive, and I rely on her wisdom. She also knows me better than just about anyone.
So I blurt out, “Men are just… mean.”
“Didn’t we know that already?” she replies, unimpressed.
“No, this is different,” I insist, and I try to explain it to her in the best way I know how: storytelling.
I tell her about my six-mile date with Sven and his dismissive shut-down. But he’s just one of many men — both in real life and online — who haven’t so much tried to date as denigrate me.
I tell her the latest on Rex*, a multi-year flirtationship I’d blocked years earlier after he declared his romantic disinterest in me and then violated my boundaries with his relentless (and unwanted) suggestive DMs. He’d just resurfaced after he saw my dating profile, and asked me out. And for the first time, he seemed in earnest; he told me how disappointed he was in himself for never acting on his feelings for me. Bewildered but intrigued, I said yes, only to go on a miserably dull date that ended with him telling me, “I thought I could get out of my head and feel attraction for you, but I can’t. I’ll own that.”
Sunny groans. She’s known about flaky Rex for ages. “Why did you give that bonehead a chance?” she asks.
“I’m a sucker for vulnerability,” I reply. “After all these years, I was curious.”
I’m no longer curious. But my ego is a bit singed, once again.
Then I tell her about Paul, the GenX indie wanna-be sommelier-but-actual waiter, who’d asked me out a couple months earlier and the night of our date, bailed, telling me he wasn’t in a good headspace. He’d just popped back into my Hinge messages and wrote, “So I guess you don’t wanna get a drink with me.” He offered this as a statement, not a question — and seemed belligerent, as if I’d somehow affronted him.
“Paul, I wanted to go out with you. You’re the one who’s bailed on me,” I replied. “If you’d like to meet for a drink, just ask me properly.”
I thought I was being firm but flirty.
He blocked me. Ouch.
I don’t get it, I lamented. It’s not like these men are super hot or successful. They’re men who should be aspiring to date me. “These aren’t my Harvards,” I say to Sunny, laughing. “They’re my safety schools.”
“That’s exactly your problem,” she answers.
“My problem is I can’t get into my safety schools?” I ask, perplexed.
“No, Dana,” she says. “Your problem is trying to date down.”
I sip my Spritz and swirl the glass thoughtfully, listening to the clink of the ice cubes as Sunny’s words sink in. Then she continues and affirms that yes, these men have been mean to me. And the reason I’m seeing a spike in meanness? It’s because I’ve started dating men who aren’t worthy of me.
Did I really think Sven, Rex, or Paul were smart enough to challenge me, kind enough to nurture me, hot enough to attract me, or bold enough to keep up with me, she asked?
I had to admit, she had a point.
But also, I’ve tried to date more attractive, interesting, and brainy men. They’re all so flooded with options, they can’t be bothered to pursue me. Or they’re relationship anarchists, seeking casual encounters without consequence. These options aren’t acceptable to me. That’s why I’ve expanded my search to include men who fall outside my ideal requirements.
I explain this all to Sunny and she says, “You may be right. But also? You’re overshooting.”
The unattainable men I’ve described — the proverbial 10s — are mostly indifferent or assholes, because they can be, she says. But they’re not purposely cruel. At most, they’re ego bruisers, because no one likes to be ignored. It’s just not personal. These men have no intention of settling with just one person. But Sven and other men I’ve tried to date recently? They’re like 3s, maybe 5s, tops.
“You’re more attractive, accomplished, and interesting than any of them,” she says. “They should be elated to have a shot at you. But that’s not how it works, because they’re too insecure to shoot their shots. They resent you.”
“So instead of pursuing you, they get off by knocking you down.”
I stare at Sunny, dumbfounded by how much she gets this. “Is this a thing?” I ask.
“Oh, it’s definitely a thing.”
“So I’m not crazy for thinking the cruelty is the point?” I ask.
Sunny shakes her head, and then drops her final knowledge bomb. “Don’t date down, Dana. It’s not safe. Men can always sense it, and will take it out on you.”
I heard from Sven one final time. He texted me before I even got home from our walk.
“dana thank you again for using one of your times for me. i enjoyed our walk. all the best for this year and i hope you realize your goal of writing for 2024. warm regards, steven.”
He’s written me ostensibly to be polite, but in reality to be cruel. This was his petty power play, a small gesture to dominate me, just as his actual conversation criticism had given him the upper hand for our second lap around the lake. He wanted the last word: to underline his rejection of me, in writing.
It stung at first read. Were my shortcomings really that egregious, I worried? But revisiting his words now, I’m bemused that this man rushed to text me the dating equivalent of a corporate form rejection letter.
I’ve also realized that for someone who allegedly didn’t ask questions, I sure learned a lot about Sven: his work, his kids, his volunteerism, our mutual acquaintances. I asked, he answered. And I heard him just fine.
This had nothing to do with Sven/Steven not feeling heard.
It had everything to do with him wanting to disparage me.
He heard me say “I’m talking too much” and identified it as my insecurity. Then he flipped the whole vibe of our conversation with his accusation, aimed where I was most vulnerable — and just as we had to walk another two miles together, too.
If I was such bad company, why did he invite me on that second lap?
The cruelty was the point.
It no longer works, now that I recognize it.
I took that selfie by the lake ahead of our walk for a reason. Knowing recent dates had ended similarly, I wanted to ensure I could see myself as I am, not as how my dates made me feel.
I stare at the photo now. My hair looks audacious. I see my quirky features, wrinkling into the wisdom and experience of my years without the benefit of Botox, as many women my age do as basic maintenance.
I also see my bright smile, my sense of style, and a spirit shining that transcends my imperfections. I’m not the sum of my physical assets and flaws. I’m much, much more: creative, resilient, wise, and a helluva lot of fun — and kind of cute, too.
Sure, I talk a lot. It’s a feature, not a bug.
And my sense of self is not negotiable. Anyone trying to disparage it isn’t worth another lap, or another question from my inquisitive mind.
Sunny is right: I don’t need to date down.
Any man worth dating will need to meet me where I am.
(This essay originally appeared on Medium in Age of Empathy in July 2024)
Thanks for reading.
I’m Dana DuBois, an essayist and GenX word nerd living in the Pacific Northwest—and founder of I Write Out Loud and co-host of The Daily Whatever Show. Through memoir writing, I explore the larger cultural forces shaping relationships, feminism, parenting, media, modern dating, and life in mid-flight. Em-dashes, Oxford commas, and well-placed semi-colons make my heart happy.
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I’m a 67 year old woman that has gone the route of online dating. What a completely shitty experience. One guy, halfway though my first drink, tells me he’s not really divorced. He’s just separated. I smiled and made some excuse to have to leave. The jerk actually got up to walk me out and on the way, had to hide because his wife’s bff was sitting at a table we had to walk by. I laughed at him, turned and walked away. I also turned back and said, just loud enough for the bff to hear, “You shouldn’t be on tinder if you’re not really divorced. That’s a slap in the face to your wife!” Then I walked away. As I got in my car, I actually gave myself a fist pump. It’s not fun out there, and at my age, the men are leftovers. I’m much happier single. Way less aggravation.
Being a woman, over 50 and single, but wanting a true companion, is I find a lonely place at times. I am quite independent, and feel, as you do, that I should have a partner, someone who appreciates what I bring to the table. Well adjusted and confident men seem so hard to come by. Which brings me back to articles I have been reading for some years, that it is not our daughters who we are raising incorrectly it is our sons. These articles are few and far between, and the more I observe the more I have come to believe that these articles may be onto something. We teach our daughters they can be and do anything, that they are valued, love, appreciated, and their relationships should also reflect that. We teach them that relationships are a give and take, sometimes you the lead and sometimes your partner takes the lead, but its a complex dance, where you must read the other and lead or follow as the situation necessitates. I don’t have a son, but I see others with sons, and even my most well meaning and intentional friends are allowing their sons to forget that they are simply equals to the others in their lives, not more or less. They forget to tell their sons, that sometimes they need to step back and let the other person lead, to know when your partner needs a hand up and when they need a hand off, and that bad behavior cannot be unaddressed by a “boys will be boys” mentality. I wonder if in part what we are seeing is how we ourselves and how women our age and younger have been raised, confident women raising more confident women, to see our value, to be proud of our independence, to want a true partner - and maybe how we raise boys has not yet caught up?