How to Know If You've Found the Right Therapist (And When to Stop Second-Guessing It)

I get asked some version of this question a lot — on consult calls, by people who've been burned by a bad therapy experience, by people who've been thinking about starting for months and can't quite pull the trigger. So I wanted to answer it honestly, including the part about what makes me specifically a good fit for certain people (and not others).

You've been meaning to find a therapist for a while now. Months, maybe. You've googled. You've read bios. You've opened a contact form, stared at it, and closed it.

Something stopped you.

For most people, that something is a question: What if I pick the wrong one?

It's a fair concern. Fit genuinely matters in therapy — more than credentials, more than modality, more than anything else. But here's what I also know: the fear of choosing wrong is one of the most reliable ways to never start at all. So let's actually answer it.

What I've watched over the years — and what lines up with what therapists are actually trained to care about — is this: the quality of the relationship between you and your therapist predicts whether therapy helps more than almost anything else. Not the approach. Not how many letters are after someone's name. The relationship.

What that means practically: you need to feel safe enough to say the real thing — not the polished, reasonable version of it. Green flags to look for:

Here's the part nobody really says out loud though: some of fit just comes down to energy. There's a piece of it you genuinely cannot assess from a bio, a profile, or even a consult call. Finding a therapist is a little like dating that way — you can do all the research you want, but sometimes you have to meet a few people before something clicks. That's not a failure. That's just how it works.

I work best with people who are self-aware but stuck. You've probably already read the books. Maybe you've been in therapy before. You understand yourself better than most people do — and you're still here, still in the same patterns, still wondering why knowing something doesn't make it easier to actually change.

That gap between insight and change? That's where I work.

My clients tend to be people who feel like they're barely keeping up — with work, with relationships, with themselves. They overthink everything, put everyone else first, and have been meaning to deal with their own stuff for years. They come in with anxiety, ADHD and executive function, depression, or some combination that's been hard to untangle on their own.

My approach is direct and warm. I'm not going to nod at you for 50 minutes or tell you to journal more. We're going to actually dig in — and you're going to leave sessions feeling like something real happened.

Not every therapeutic relationship is a good one. You're allowed to trust your gut. Here are signs something isn't working:

A good therapist will welcome a direct conversation if something isn't working. If that feels impossible, that's information.

"The fear of choosing wrong is one of the most reliable ways to never start at all."

First, let's just name the obvious: talking to a stranger about your personal life is weird. Even if you've been in therapy before, walking into a new room with a new person and being expected to open up takes some getting used to. That's completely normal, and it doesn't mean anything is wrong. (If you want more detail on what to expect, I wrote a whole post on what happens in a first therapy session.)

Our first session is a real conversation, not an intake form with a pulse. I want to know what's bringing you in, what you've already tried, and what you're hoping will actually be different this time. I'll ask questions that might surprise you — not just about your history, but about how you think and what keeps the patterns running.

I treat the first appointment as a trial run — intentionally. After we meet, there's no expectation that you're locked in. No recurring weekly slot I'm holding for you. No awkward conversation you have to have if it didn't feel right. You come in, you see how it feels, and then you decide if you want to continue.

You don't have to have it figured out before you come in. You just have to show up.

I've had clients come to me after six months or a year with another therapist saying they never felt like that person really got them — but they stayed because they didn't want to start over, or they weren't sure if that feeling was just them. It wasn't just them.

If after three sessions you still don't feel like your therapist truly gets you, trust that feeling and keep looking.

Three sessions is enough time to get past the initial awkwardness and get a real read on the fit. A few things to pay attention to as you go:

You don't have to feel fixed. But you should feel like something real is happening.

If you've been sitting on this for months, waiting until the timing is better or you're sure you're picking the right person — that's the overthinking doing exactly what it always does. It will always find a reason to wait.

The only way to know if we're a good fit is to find out. First appointment is a trial run. No pressure, no commitment, no breakup required if it's not the right fit.

You've been thinking about it long enough.

Book your free 15-minute consultation — no pressure, no commitment, just a conversation to see if we're a fit.

— Angela DeGiaimo, LCSW | NY State of Mind Therapy Telehealth therapy for anxiety, ADHD by telehealth, and the messy work of being human | New York State