What It’s Like To Date As a Therapist

The good, the bad and the downright awkward…
Published March 7, 2025

(Image: Getty Images/Canva)

It’s a Wednesday night, and after a full day of nodding, listening, and subtly guiding clients toward their breakthroughs, I should be in my comfiest trackies, deep in Netflix. But no, I’ve rallied. I’ve done my hair, swiped on lipstick, and gone on that Hinge date my friends begged me not to ditch.

He’s cute, like, actually cute, and as we settle into our seats, drinks in hand, the usual first-date small talk begins. And then, barely fifteen minutes in, he asks- what do you do? And so it comes, I drop the T-bomb. “I’m a therapist.” And like clockwork comes the inevitable smirk, followed by the all-too-predictable: “So, what am I thinking right now?” If I had a dollar for every time I’d heard that on a date, I’d be sipping cocktails in Santorini, not dissecting Melbourne’s dating scene over a mediocre pinot.

As a single thirty-something navigating the wild west of modern romance, I’ve got no shortage of dating tales. But does being a therapist make it easier, or infinitely harder? Honestly, I do not know. But here are some standout moments, so I will let you be the judge.

1. Prepare For People to Open Up—Fast & In Painful Detail

It’s the third or fourth date with a man who’s recently divorced. The vibe is good. The conversation is flowing. And since he has finally mentioned his past separation, I figure it’s the right time to ask. Big mistake.

What I thought would be a breezy overview turns into a full-blown, unfiltered, hour-long TED Talk on his divorce, complete with emotional flashbacks and unnecessary legal details.

Don’t get me wrong, empathy is my bread and butter. As Brene Brown puts it, “Empathy is communicating that incredibly healing message of… You are not alone.” But how much empathy is required in the early stages of dating? Because by the time he finishes, he exhales dramatically and says, “Wow, that felt like a therapy session.” And I’m sitting there, sipping my drink, thinking… “WOW this is just so not sexy.”

2. The Wild World of Dating Apps (aka Potentially Running into Your Client’s Dad)

Swiping through dating apps is already a jungle, but add being a therapist to the mix, and suddenly it’s Survivor: Hinge Edition. Because here’s a fun twist: What if a client pops up? Or worse… their dad?

Yes. This happened to me. I opened the app, saw a heart, a message, and immediately turned BRIGHT red. My survival instincts kicked in. I slammed my phone down, hid under my bed, and considered moving cities. It was awkward beyond words and led to a very fast supervision session.

And while we’re here, let’s talk about putting my profession on my profile. Do I risk attracting men with unresolved childhood trauma? Or ones who think I’ll psychoanalyse them over cocktails (as above)? I worked so hard to become a therapist, and I’m incredibly proud, but honestly, it’s safer to just put “mental health” and call it a day.

3. Turning Off My Therapy Hat & Being Blindsided

“Jamie, he is so controlling.”
“Jamie, he’s a narcissist.”
“Jamie, he is gaslighting you.”

That was my friends, trying (and failing) to shake me out of a bad relationship. And look, I of all people should have seen it. I can spot these behaviors from a mile away when it comes to my clients’ dating lives. But my own? Fully blind. It was like my therapist brain took a holiday the moment I caught feelings.

And of course, it got worse. Cue my own therapist saying, “Jamie, can you see that you fell in love with a man exactly like your father?” How does that make you feel? MORTIFIED I tell you. 

4. Having My Profession Used Against Me

And then, there’s that guy. Mid-date, out of nowhere, he looks me dead in the eye and says, “HOW are you a therapist? You have no empathy.”

Excuse me, sir?

Upholding boundaries doesn’t make me unempatheti—it makes me a functioning adult with standards. But sure, let’s call me heartless because I didn’t laugh at your barely passable joke. (Cough, narcissist.)

5. Remembering. Everything. They. Say.

My job requires me to really listen. Which is great for my clients- but for the guys I date? Terrifying.

Take this one time: First date, going well. He casually mentions his birthday is later that week. Fast-forward a few days, and I’m agonising, do I text? Do I say nothing and pretend I don’t remember? Is it weird to remember? I went for the casual birthday message, and thankfully, it landed well. But let’s be honest, dating a therapist means we will remember everything you say, and you will constantly wonder if we’re analysing you. 

And as for what it’s actually like to date a therapist? Well, that’s a question for my exes, and maybe the next article.

The Therapist In Therapy by Jamie Maserow

$36.99

Jamie Maserow
Jamie Maserow is a Melbourne based therapist and author of her first book The Therapist in Therapy.
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