For the New Year, I wanted to invest more in myself. That included signing up for a monthly massage, pursuing treatment for mild sleep apnea, and – the most quintessential of self-health tropes – getting a therapist.

I have long been pro-therapy. In late college, I briefly saw someone – and then busyness got in the way, which is not as much a cause, but in fact an excuse and even more so a symptom of why I should see a therapist. I also frequently encourage friends to pursue therapy. It’s important to talk through your feelings and circumstances with an objective third party. This is what I do to strangers at parties. Which is why, after 2020, I needed to find someone to deliver weekly monologues to.

Conveniently, my workplace offered a handful of therapy appointments for free. Originally posed as one-time sessions as part of employee appreciation, I showed up to my Zoom session with “Kathy” with a single goal: What questions should I ask when looking for a long-term therapist?

Kathy was a 36-year-old Kentucky mom of two who married at 34 after thinking she’d never find the right person. She also has a sister who spoils her two daughters rotten; Kathy really struggles with this. Kathy hangs out with neighbors on her court every weekend (socially distanced of course! though I’m not so sure); they even had a New Year’s gathering together. She tends to vote Democrat.

How do I know all this? Well, Kathy told me.

“Sounds like your therapist has boundary issues,” my friend remarked after our first session.

At that session, Kathy told me this – and a bit more. That I should have some idea of what concerns I wanted to “work on” (my choice language) when seeking a therapist. That I should ask about the therapist’s philosophy. For example, do they assign homework?

“Homework?” I asked.

“I think it’s important to put time into your therapy outside of your weekly sessions,” Kathy said. “As much as you put in, you get out. I sometimes ask my clients to do some tasks between sessions.”

That didn’t sound like a deal breaker for me.

Kathy also told me my company had decided to extend their generous offer. I could attend free Zoom therapy with Kathy for the foreseeable future without touching my health insurance deductible. Amazing. (“Frugality” is an area of improvement for me along with commitment, as we shall see.)

My first homework assignment was to decide on a word that matched my intention for 2021. What was this, vinyasa yoga?

I spent the week thinking intentionally on this. I even made a list in my phone. I prepared to show up the following week to discuss my list. Kathy’s 2020 word had been kind. I considered grateful, but that sounded trite (I did decide grateful sounded less clichéd than thankful). I also pondered Unapologetic, but that sounded rebellious. I landed on Unashamed.

At our follow-up session, Kathy never asked what my intention for the year was. Instead, we discussed a minor stress at my job, a recent first date, and revisited my frustration with partisan conspiracy thinking that I often encounter when interacting with family members.

At our initial meeting, I laid out several issues I wanted to address: Commitment. Sexuality. Tension with my family about politics (where politics is really a placeholder for delusional thinking and rejection of facts – if you know, you know). Low-key anxiety about my future and self-sabotaging habits (“I’m not that anxious, it’s just on my mind”). Kathy professed she felt comfortable with these topics and had worked with similar clients before.

I fast realized Kathy was the friend of a friend I would meet at a cookout and quickly bond with while we refilled our sangria glasses. I would tell stories to make her laugh. We would discuss workout routines or possibly what book club we last attended whose book we didn’t read.

Something I have realized in the last three years is that I am a performer. For better or for worse, I have always been good at shaping my personality to match what others expect of me. It is not that I am lying or fabricating myself, but I can find the right angle that is socially acceptable and endearing. I want people to like me – a ubiquitous wont of us mortals! I wanted Kathy to like me! But being liked is not the point of therapy. I want a therapist to challenge me. Instead, I felt continually affirmed.

When I expressed concern that I will have no roots in ten years due to flighty prerogatives, Kathy relayed her own anxiety at “my age.” When I discussed dating escapades, she encouraged me to continue experiencing things. When I ranted about loved ones who believe the 2020 election was “stolen” and have no evidence other than watching CSPAN airings of cases that were rejected by courts, Kathy nodded sympathetically and agreed it’s hard.

Kathy was my friend, not my therapist. I tried telling her as much at our third meeting. “You’re the person at the party I would befriend,” I said. “I have this terrible habit that I want people to like me, and I feel like I do that with you sometimes.”

Kathy didn’t ask, “Why do you think that is?” She just laughed with me. (Admittedly, I laughed through that confession. Classic downplaying; always laugh when saying something serious…) I probably also didn’t have to let her fill the silence too much because filling the silence with additional words is also my special talent.

Not 15 minutes later, Kathy held up a self-help book on her desk. “Now I’m telling you this as a friend,” she announced, “you need to read this!”

No, Kathy, no! I’m not your friend.

At our final session, Kathy assigned me a book to read: The Obstacle Is the Way – a 2014 self-help book popular in sports and entrepreneurship circles. I fake smiled. If I wanted Dr. Phil to pop psych me, I had found it.

“I just love seeing you,” she gushed in the last 30 seconds before we clicked off screen. “You always brighten my day! See you next week!”

I claimed my work schedule conflicted with our next appointment. She asked when I was available again. I have not replied. My next therapist will teach me how to better break up with people.