the surgeon situationship

with lessons for anyone dating in the gray zone

He was tall, which is important — but not that important — but important enough. Handsome in that competent, military-doctor way: masculine yet slightly boyish; a man who knew the difference between a tibia and a fibula, but also rated every movie he watched on IMDb like it was his job. He wore a literal uniform. Three of them, I think. Anyway, I swooned.

We met on Bumble. Which is to say, we met on the internet — something I loathed to do — which is to say it was like meeting in a bar I was dragged to at 3 a.m. by a friend who didn’t know any other places that were open. A place where everyone is lying about something and no one is paying for their drinks.

He asked me questions about myself that seemed genuine and deeper than “How was your day?” He asked about my writing. He was curious about my family and my time living in PEI. He used full sentences with punctuation — proper grammar and spelling. He ended texts with periods, and better yet, question marks. At one point, I thought: What’s the fuss about online dating? I’ve found a good one. It felt like this is what dating is supposed to feel like at this age — hopeful, warm, full of Oxford commas.

I was wrong.

We slept together once. I say “slept,” but that implies rest. It started off as a spontaneous evening — not a typical “u up” text. He asked me if I wanted to play strip poker. I was intrigued. He had just come back from two months on a ship. He was in the city, he wanted to see me. I was in my pajamas. We’d been talking for almost six months at this point — with a month of no contact in between (which I’ll get to later). I thought, If we’re gonna fuck, it’s now or never.

I got out of my pajamas and into a sweatshirt, tank top, and jeans. I debated putting on some socks. Not because I’m some prude, but because I didn’t want to lose so easily at strip poker. It was my first time playing; I knew I was an easy target. And if you know me, I hate losing, especially at games where the stakes are laughably low.

It didn’t feel particularly romantic. But it’d been a long time coming. I thought strip poker would be a fun touch — a way for us to reconnect in person, something we hadn’t done in over three months. Of course it was awkward. All of it. Not disastrously so, but just enough to feel like something was… off. I assumed it was us being almost strangers — like pen pals suddenly expected to make eye contact and flirt. Like people suddenly released into the wild and expected to just… know. It was Nell, but with less tree talk and more tongue.

But he also had a cute new haircut that showed off his boyish good looks, and he was good with his tongue and fingers. It wasn’t a 10 on IMDb, but it was a definite 7. I’d recommend him to a friend.

Afterward, I thought we would do it again. It was the beginning of summer. Sand, sun, and sex just go together when sweaty thighs start to stick together. But if I was being totally honest, I really wanted to build something. Explore things. That’s what I said to him before his deployment when I wasn’t sure what to expect (another red flag), to which he agreed.

I said, “I like you, and I want to explore things, get to know each other better, and see where this goes.” It wasn’t in the Gen Z “explorationship” terms — I’m far too old and tired of ambiguity for that — but in the “let’s spend time intentionally together” way, which I texted him the next week after his post-sex follow-up: “I had fun last night. How was your Sunday?”

It seemed like he wanted the same. It felt like an invitation for more to come — instead of what my gut rightly felt: it was just a line. Something he was really good at. Writing words that felt like something — with really great grammar! — but were, in fact, a whole lot of nothing.

He didn’t disappear. At least not at first. And I suppose that’s what threw me off. Because, as disgusting as it sounds, if a man doesn’t ghost you after sex, then that’s a green light. Well, maybe an amber light. Proceed with caution. He seemed like he was interested, and I’ve noticed I’ve said “seemed” one too many times. Because when a guy is interested, he just is.

Here’s the thing about dating in your 40s — and being a dating and relationships writer: you think you’ve learned something. You’ve read the books. Been to therapy. You know what an avoidant attachment style looks and sounds like. You know what to look for.

But then a hot Navy doctor slides into your life with good spelling and a jawline, and you forget everything.

“Above Average Attractive” Navy Doctor: all text, little action (well, except for sex)

Not because I’m an idiot who hasn’t learned anything — but because I’m human. I’m a single woman with a big heart and an unruly black cat who is swiping on guys, asking one of them to love me (when warranted and vetted, of course).

But my point is: it happens to the best of us. And it doesn’t make us bad or wrong. It just means we haven’t met that person yet. Even when we really, really want to. And that doesn’t make us desperate. Again, that makes us human.

But some people aren’t on your timeline. Or built for long-term connection. Or maybe both.

I could call him a fuckboi. But that feels too modern, too simple. Too reductive for both him and myself. He was more like a Situationship Surgeon: quick to assess, efficient in detachment, emotionally sterile. And I was the patient who didn’t ask enough questions before the anesthesia kicked in.

The last time we conversed — via text, a week after — he highlighted our chemistry, which I guess was apropos and on brand for a doctor. It’s scientific. A measurement of something. 1+2=3. It doesn’t live in the liminal space for him. Although for six months of us texting back and forth with a handful of IRL meetings, he sure did like to frolic in the gray zone.

The chemistry wasn’t there. Or something. He didn’t flat-out say that, but he didn’t not say it either. He mentioned something very specific. A sexual act. It sounded almost clinical, the way he verbalized it — which isn’t surprising, considering he’s a doctor. It was like asking me whether I smoke a cigarette or not. Do you smoke? Do you enjoy smoking? How much are you willing to smoke?

I said I liked smoking just fine — if the parameters and trust and respect were in place. I’m not going to just smoke for anyone. I’ve got my health and my own comfort to think about for crying out loud.

He was hemming and hawing, so then I said, “Maybe this is a conversation best suited for a phone call.”

He said he was in the middle of watching the NBA finals with his friends.

And I remember thinking: How is this the most appropriate time for a conversation like this one?

“Oh, look at that three-point shot! So… about our chemistry. How did you feel about it?”

I felt like an afterthought — which, in retrospect, I think I always was.

Just a quick debrief: there had been a gap in our conversation for about a month while he was deployed. I chalked it up to him being important on a Navy ship, and that very well might’ve been true. But it was also true that if he wanted to, he could’ve sent a quick message, even just to say he’d text me back when he could.

Instead, I reached out. I asked how he was — just like I did when I didn’t hear from him for a week during the first two months of us seeing each other. I even invited him over to watch the movie he suggested we watch. Subtle red flags, but red flags all the same.

Not too long ago, I made a declaration to myself: I wouldn’t live in fantasyland anymore when it came to dating. That I would speak up for myself, be vulnerable, communicate my needs and desires, and — more importantly — take action.

I did that. I might’ve fumbled along the way — much like the Indiana Pacers, who ended up losing the game that night — but I stayed true to myself. I took action by getting on that app in the first place. I communicated clearly and honestly, and with so much emotional intelligence — maybe a little too much — that the Gottmans themselves would probably tell me to relax… or hire me as a therapist.

I showed up. Which is more than I can say for him.

Yes, he was available… but not emotionally.
Yes, he responded… but rarely took initiative.
Yes, he showed up at my apartment — twice — but probably only for sex, which happened once. (When he came over for movie night and it didn’t happen, he asked what our “vibe” was and why there hadn’t been any “intimacy.” Yes, another red flag.)

In six months — two of which he was away — that was it.

So I’m thinking that when he looked at the hand he was dealt with me — and what was being asked of him: emotional availability, intention, maturity — the royal flush of dating requirements — he decided to fold.

I texted him a few days later, saying how it was painfully obvious to me that this was going nowhere, but how I had hoped he would’ve been upfront in the beginning. I also noted how uncomfortable I felt about his smoking comment.

I still wished him a good summer.

When Hot Navy Doctor (I think “hot” is pushing it a little, but it has a better ring than “Above Average Attractive” Navy Doctor) bounced, I was disappointed, but I wasn’t surprised.

As I said, there were questions I wished I had asked — red flags that had been waving in my face like I was at a NASCAR race.

So to save you time — and if I could go back in time — here are the questions I would’ve asked. Not just to "get answers," but to give you clarity on whether the person you’re interested in is emotionally available, genuinely interested, and aligned with the kind of connection you are hoping to build.

Before things get physical:

1. “What are you actually looking for right now?”
   Not in a “scare him off” way, but in a direct “are we playing the same game?” kind of way.
   

2. “How do you like to get to know someone?”
   Is he a texting guy? Does he prioritize in-person connection? His answer would show whether he had space in his life — and mind — for you.
   

3. “What does a healthy relationship look like to you?”
   His vision for partnership would say more than whether he was “open to seeing where things go.”
   

4. “Have you ever built something meaningful with someone before?”
   Not to dig into his past, but to understand if he has the capacity (and interest) in long-term emotional intimacy.
   

During those early texting months:

5. “What makes you keep reaching out?”
   Especially if there were gaps in communication — this would’ve helped clarify whether he was breadcrumbing or genuinely circling back with intention.
   

6. “Are we on the same page?”
   Simple, bold, and underrated. If someone can’t answer it with clarity — there’s your clarity.
   

7. “How do you handle things when you're not sure how you feel?”
   Tells you if he’s the kind of person who avoids, disappears, or communicates.
   

Before (or after) sex:

8. “Does having sex change anything for you?”
   It shouldn't — but the answer reveals his maturity. If he flinches or deflects, that’s your answer.
   

9. “Is there anything you’re unsure about with us right now?”
   This invites honesty before you’re tangled up in mixed signals.
   

10. “Are you still figuring things out romantically, or are you clear on what you want?”
    You deserve to know.
    
    

So back to the dating drawing board I go. I do so with a bit of a heavy heart — it really is a battlefield out there — and for all the downfalls of Above Average Attractive Navy Doctor, there were qualities about him I liked and wanted to explore further. But I go back with some hope and excitement, too. Because we all need that. That’s how we proceed. That’s what feeds our hearts and souls when the carpal tunnel kicks in after swiping left for so long.

I’d like to think I’ve learned some valuable lessons from my Surgeon Situationship — and that’s all we can really do for as we dodge this dating minefield.

And hey, at least I got laid! With an average movie score equal to The Godfather Part III or Fast & Furious 6: entertaining, maybe even a little memorable, if not retrospectively blurry. They can’t all be Oscar winners (even if some men would like to believe their performances are award-worthy).

Maybe that’s okay sometimes — that we get to try some people on for size. Because dating is all about that: figuring it out — both ourselves and what we want. And we deserve the royal flush. At least, that’s what I’m holding out for.

Thanks for being here.
Love, Brie xoxo

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