I Went on My Third First Date in Over Six Years
(The first was too hot. The second, too cold. Would my third first date be just right?)
I was pursuing my perfect bowl of porridge
When I decided to start dating again — in my 50s and after a nearly seven-year gap — I made a promise to myself: I would only date men who excited me. I know all too well the time and energy suck dating can be. Unless he seemed amazing, I’d pass.
One unintended outcome of this resolution? I became the pursuer, instead of the pursued.
It’s been… uncomfortable.
But I’m kind of good at it. I’ve now asked out — and gone on — three first dates in the past month, with results that made me feel like a romantic Goldilocks:
The first first date was too hot.
The second first date was too cold.
Would my third first date be just right? I hoped so. It had been a lot of time — and pursuit— in coming.
I’d had a crush on this guy for months.
Last year my bestie and I attended an arts gala and at our table sat this beautiful man. He was tall, slender, sable-skinned with long braids, immaculately dressed and accessorized — he had the coolest arrangement of rings I’ve ever seen — and his long, sinewy hands made me blush, they were so indecently gorgeous. He had a gentle presence and warm smile and ugh, I couldn’t look straight at him; like an eclipse, I feared I’d be so blinded by his radiance I’d never see again if I gazed at him full-on.
Eventually we spoke and I learned he’s an author, at the gala because the organization had featured his book. Swoon.
I figured a man that pretty and accomplished likely wasn’t single, or straight, or age-appropriate, or interested in me.
At the end of the night, our fun-loving table mates all exchanged contact info, so I got his digits without trying. How could I not shoot my shot? I messaged him and asked for the name of his book. He replied, I ordered it, and texted him a photo of me holding the book once it arrived.
He thanked me, and that was it. His book languished on my nightstand for months, as most of my books have.
Fast forward a few more months. The same friend who took me to the gala texted: “Guess who’s on Bumble?”
There he was. Single, seeking a woman, and exactly my age. What was a smitten girl to do?
I finished his book.
And then I texted him and told him I thought it was beautiful.
He took a couple days to respond, but eventually wrote back and thanked me effusively, and suggested we get together to talk about it. I was giddy. A few more weeks (and nudges from me) later, we settled on a place for dinner and cocktails.
Was I going on an actual date with this beautiful, talented man, after all this time, and effort, and delays?
I think I was.
I was too nervous to eat. My mouth had other plans.
The day arrived and so did I, wearing a cute dress with a peek-a-boo matching vintage slip, a cardigan, and my favorite boots.
He walked in moments later, all smiles and just as gorgeous as I remembered. We ordered cocktails — an old fashioned for me, something fancy and French I can’t recall for him, except that we laughed at how we both enjoy ordering cocktails where we don’t recognize at least two of the ingredients. Our drinks arrived quickly and I was grateful to have something do with my nervous hands and mouth.
My hands stayed to myself all night, regrettably. But my mouth was in overdrive and I. Could. Not. Stop. Talking. I am a storyteller and extrovert by nature, but this was like I had an out-of-body self telling me, you’re talking too much Dana, but talking Dana was too overstimulated to do anything except apologize. “I think I’m talking too much,” I said more than once, though he just laughed and assured me I wasn’t.
But I think I was? Ever since that night, I keep thinking of half-heard tidbits and stories unanswered as our conversational topics overflowed one atop the other, my mouth the source of the deluges. Perhaps my logorrhea was a compensation, an output run wild while my other senses were rattled with giddy nervousness.
The restaurant I’d picked served fancy Creole. There was no way I could taste or feel hunger at this point, but I had to order something, and actually said out loud, “I’ll have the étouffée because it’s fun to pronounce.”
If you’re wondering how much game I’ve got, well, now you know.
Our dinners arrived, along with another round of beverages. I stared down the étouffée, a soupy rice dish with sausage and seafood and spices throughout. I chuckled inwardly, recalling my Goldilocks dating wish.
It didn’t look unlike porridge.
But was he just right?
I was unable to choke even down a mouthful as I tried to figure it out.
We shared stories as I drank my dinner. We talked about his book, of course, and especially the protagonist, who was baffling to me, a figure who seemed like an emotional blank slate amid dynamic locations and ancillary characters. My date confirmed that the neutrality was intentional, which felt affirming — I’d grasped the narrator he’d created. So this is how you build a world around a character, rather than make the character the central focus. Fascinating.
I pondered, is that who he is, at least to me? For all my crushed-out nervousness, I couldn’t read my date at all, just like I couldn’t grasp the intentions or emotions of his protagonist.
He was attentive and smiled a lot and seemed to encourage my storytelling, sure, but did he… like me? Find me attractive? Want to make out with me? Did I even want to make out with him? I could’ve been staring at a marble statue for how much of a vibe I picked up during our nearly four-hour dinner that I didn’t eat.
We stayed so long our server sheepishly approached the table at 9:45pm and nudged us along, stating they’d been closed for 45 minutes. We apologized. He surprised me by picking up the tab. I thanked him and asked if he wanted to get a nightcap elsewhere. He declined.
Instead he walked me to my car, and we stood outside talking a few minutes more, each shivering into our coats against the gusty, frigid January night as cars on the main thoroughfare rushed past. I wasn’t ready for it all to be over. But he leaned in and our date ended with a hug and his enthusiastic but noncommittal, “We should do this again soon.”
Then he walked off, leaving me buzzing and bummed out on the sidewalk from too much booze and frenetic energy and nowhere to put it.
Before I left for my date, I texted my housemate with where I’d be, because safety first. I told them I was nervous and they replied emphatically, “Stop downplaying yourself! Walk into this with the mindset of ‘what does he bring to the table for YOU?’ How do YOU feel around him?”
This was excellent advice and I absolutely did not heed it.
He certainly brought a lot to that table. He was kind and responsive and gave me plenty of space to express myself. He was an excellent date.
What did I bring to the table? Well, I referred to my speaking style as diarrhea of the mouth. I called myself an idiot three times, and used the word “nervous” five. I brought a lot of self-deprecation to the table, and that’s just not like me. Turns out, spending those nearly four-hours chatting with my date didn’t make me feel all that great.
If I felt not right, how could I have expected him to be just right for me?
This wasn’t his fault. Being a romantic pursuer is hard. After three rounds of it — not to mention a prolonged crush on this guy — I think my emotions had a momentary meltdown, one that’s abated but lingered ever since. All of which created just the sort of dating energy suck I wanted to avoid.
I lost sight of myself at that table in my nervous (there’s that word again) haze. But in truth, I’m a thoughtful speaker who can hold a conversational partner rapt with a good story, and one who adores listening when my partner does the same. Nervous isn’t my nature, and I rarely worry I’m an idiot. I love the idea of meeting someone who rattles my nerves with excitement… at first.
But only if he calms them shortly thereafter by assuring me the feeling is mutual.
I am not Goldilocks.
I’m not a lost child. I’m not wandering into a bear’s den to forage for sustenance: emotional, romantic, or literal. I don’t need to settle for gruel — at any temperature. I don’t need to sneak into a strange bear’s bed — no matter how comfortable.
What I am is a complex, brainy, sorta demisexual, assertive, emotionally intelligent woman with a full-to-overflowing life. Dating isn’t going to be a fairy tale.
I wouldn’t have it any other way, as I love my life, and girls don’t tend to fare too well in fairy tales.
But what is dating going to be like for me, now?
My date and I have texted a bit. He halfway suggested getting together again, but has taken no steps to make it happen. The same thing happened after those first two dates: interest, outweighed by indifference. I have a strong aversion to apathy, but I’ve made peace with it as the result of my romantic pursuits, mostly.
I’ve left the door (and chat windows) open with all three fellas. If there’s to be a second date, then it’s on them to walk through it and pursue me.
If that happens, great. If not, that’s fine too.
I’ve done what I can. I took on the work; that part feels good. It’s empowering to know that the next time a man strikes my fancy, I feel confident I could do the work pursue him.
But also, I kinda hope I won’t have to? As much as I’ve learned from going after what I wanted, it’s also dawned on me — shouldn’t dating be… fun?
I think I got so immersed in the effort of pursuit that I lost sight of what I was pursuing. I may not be Goldilocks — or Snow White or Sleeping Beauty or Cinderella, or any other damsel-in-distress princess in a fairy tale. I’m seeking a man, not a prince. But still, I want him to be charming, and charmed by me. Dating should be fun.
And silly, and energizing, and flirtatious, and affirming, and sexy, and arousing, and giddy. Especially first dates.
Dates shouldn’t feel like work.
They should feel… just right.
{This story originally appeared in the Age of Empathy publication on Medium on January 30, 2024.}
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Greetings!
I’m Dana DuBois, a memoirist and GenX word nerd living in the Pacific Northwest—and founder of I Write Out Loud. I’m the co-host of The Daily Whatever Show and Editorial Director at Blue Amp Media. I write across a variety of topics but parenting, music and pop culture, relationships, and feminism are my favorites. Em-dashes, Oxford commas, and well-placed semi-colons make my heart happy.
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Hi Dana, I'm enjoying your dating stories, your passion, smarts and vulnerability. As a therapist and dating coach, I'm also always collecting people's romantic (or not so much?) experiences.
For what it's worth, it seems to me that you could reduce the pressure on yourself and your companion re: how immediate and powerful the connection needs to be, w/ your reward being more ease & fun. Looking at it through a temperament angle, you're probably in the catagory of "Romantically Impulsive" vs "Romantically Cautious" - and it can hurt when your date is constructed differently - if they need to take more time, collect more impressions, and whose emotions accrete at the pace that info is gathered. It's one reason that being similar re: impulsivity v caution helps relationships get off the ground. But it's possible to adjust somewhat, if you want to experiment. Wishing you well!
Dana, another great story. I love the reflection and I restacked with my favorite (but hard to choose) quote, "I’m not a lost child. I’m not wandering into a bear’s den to forage for sustenance: emotional, romantic, or literal. I don’t need to settle for gruel — at any temperature. I don’t need to sneak into a strange bear’s bed — no matter how comfortable."