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Illustration: Jun Cen

What it’s really like to try online therapy

With only her phone and computer as guides, Time Out New York editor Jillian Anthony braves the new world of digital therapy

Written by
Jillian Anthony

We are a country totally into figuring ourselves out. According to a 2013 survey by the University of Phoenix, 32 percent of Americans have sought counseling for mental health issues, and as in most things, New Yorkers are overachievers. There’s no city more synonymous with therapy than ours (case in point: The Sopranos, Prime, anything Woody Allen’s ever done), and we have nearly 5,000 psychologists to prove it—that’s 46 percent of the entire state’s total. The thing we don’t have is time (or money), so in an age when busy New Yorkers can get groceries, cabs and hookups without looking up from our phones, why not therapy, too?

A slew of websites and apps now offer access to therapists through text, chat or Skype—all for a fraction of what it costs to lie on someone’s couch. Since launching in 2013, BetterHelp has amassed a total of 3,000 patients that message online or text with 300 counselors; competing service Talkspace now has 100,000 users who chat with 200 licensed therapists; and some services, like video therapy platform Breakthrough, even accept insurance. Here’s the thing: Yes, having a shrink as accessible as Seamless is convenient, but can phones and screens really provide the same kind of intimacy and emotional connection that an in-the-flesh, Eames-chair-occupying professional does?

I was indoctrinated into New York’s cult of therapy when I moved here from Los Angeles in 2011 and sought help to claw my way out of a breathtaking depression. A year-and-a-half of weekly sessions with my 70-year-old licensed clinical social worker left me happy, healthy and ready to move on. Flash forward a few years to now: I’m a few months out of a relationship with a man who has the emotional availability of a banana slug, and I recently parted ways with a close friend because of his substance-abuse issues. So yeah, I wanted back into therapy. And with a lack of funds and time, digital therapy seemed like the logical, if dubious, choice.


First up, Talkspace, a service that offers unlimited messaging online and through your phone. I IM with my “initial consultant,” Matt, who asks what I want to delve into (self-improvement, lingering breakup pains), then launches straight into payment plan options, which is jarring on the heels of, y’know, spilling my guts. Once I’ve signed up for a $25-a-week plan, Matt explains that my “room” is open 24/7 for me to share thoughts with my therapist and that he or she will be online once or twice a day to respond with “digestible doses” of therapy. “If you use the mobile app,” he writes, “it really is like having a therapist in your pocket!”

Matt takes a couple of hours to pair me with Arwa, saying she best fits my needs because of her “person-centered, motivational interviewing as well as systems approach.” I don’t know what any of that means, but I’m all in! A little icon of Arwa’s face pops up with some details, including that she is a licensed mental health counselor from Florida with eight years’ experience. She types out an intro, then tells me that if I’m ever feeling doubtful or misunderstood, I should let her know. “I’m comfortable being open,” I write, then tell her about my ex, who I took back three times (I know, cringe), only to have him show me repeatedly that I would never be a priority to him. “I want to approach relationships with positivity, and I worry that I can’t,” I type. “It can be hard to break up with someone we feel strongly about,” Arwa responds. “We tend to make excuses for them. What does it say if the people we care for are putting us through stuff we wouldn’t take from anyone else?” I feel a familiar lump in my throat. I’ve long known I put up with too much bad behavior from boyfriends, and hearing it from Arwa is a good reminder. “No more,” I say out loud, committing myself to making digital therapy work for me.

Over the next couple of weeks, Arwa and I go back and forth a few times a day. Every time I shoot off a message (“I’ve had problems with standing up for myself”), she responds within one to three hours (“Tell me more about staying with your ex even though he didn’t make time for you”), so I’m never left hanging for long. She is insightful and pushes me to think, and unlike face-to-face therapy, I have a full record of our conversations to refer to whenever I’m feeling down. Then one night I have a mini breakdown, drinking away the pain after seeing my former friend on the street and having him ignore me. But despite the fact that Arwa and I have been communicating for days, it never occurs to me to contact her. Instead, I immediately text one of my friends. My friend is empathic and happy to listen, but she doesn’t have Arwa’s insight or expertise. Arwa’s got that in spades, but she’s still just…a stranger on a screen. Which makes me realize: What I really want is a friend-Arwa hybrid (so…a regular therapist?). $25/week


Still hopeful, I sign up for the similar service BetterHelp (I’ll communicate with a therapist online and via text). I immediately notice the user interface looks straight out of the AIM era, but I press on. I fill out another survey (yes, I sleep well; no, I don’t worry about functioning sexually) and say that I’d like to focus on why I repeatedly choose men who aren’t right for me. I’m matched to Brenda, a licensed mental health counselor with 13 years’ experience. Comments from other patients sing her praises—“Brenda is an awesome combination of kind/empathetic/highly trained/bravely honest”—and she gets five stars across the board.

By now, I’m used to messaging with faceless strangers about deeply personal stuff, so I launch into how I let myself get swept up with a man I shouldn’t have. She immediately asks if there are common characteristics between the men I typically date and my family members (oh, shit, Brenda, let’s get right into it then). I find it difficult to talk about my family, which I’m fiercely protective of, via keyboard. During my past IRL therapy, it was easier to work through what I wanted to say with someone there, giving me prompts. But I tell Brenda several women in my family have kept horrible partners around, sometimes for decades or a goddamned lifetime, and I worry that I will too. She tells me to try dating types I normally wouldn’t, comparing men to books in a rarely visited library section (“They might not have such racy covers, so you may have a tendency to pass them by”). I push her for advice on how to do this, and her response throws me: “Dating sites are a good way to find out more about your likes and dislikes.” Come on, Brenda—I’ve been online-dating for years. But beyond that, I’m irritated because I’m here to learn about my personhood, not go on a rom-com search for Mr. Right.

Though Brenda has been very responsive—I rarely wait longer than an hour to hear from her—and she seems sincere, I’m so turned off by her tone-deaf advice (and the ancient-feeling interface) that I discontinue my service after two weeks. $40/week

In Your Corner

By now, I’m yearning for some face-to-face interaction, so I turn to In Your Corner, which offers sessions with therapists via Skype. At $50 per 30-minute session, it’s pricier than the other options but still about a third of the price of a standard 45-minute in-office appointment. I happily find I’m able to browse therapists’ descriptions and make my own choice. Annie, a life coach with a master’s in social work, has a sentence in her bio that attracts me: “I believe that therapy arms you with the skills to face challenges, make wise decisions and discover who you are meant to be.” Yes! Let’s do this, Annie!

I book an appointment through her online calendar and nervously wait for her to appear on my screen. It’s been a long time since I’ve looked into a stranger’s eyes and shared my innermost secrets. Annie Skypes me right on time. Just like I did at my first in-person session years ago, I feel pretty awkward, but she’s so easygoing (“If I were a Spice Girl, I’d be Sporty”) that I quickly feel more comfortable. When I describe the self-loathing and loneliness I’ve felt lately, she pushes me for details and even shares her own feelings of isolation (she had a hard time watching her friends pair off before she was married). It feels likes she “gets” me more than any of the text-based services I’ve tried, and I quickly trust her.

At the end of our session, she assigns me homework: In addition to breathing exercises and meditations to chase away negative thoughts, she tells me to make an Ideal Woman List with 10 traits I’d like to embody that are “part you, part your mom and part Beyoncé.” I laugh but take my list making very seriously. I book another appointment (she works around my schedule, not the other way around), and a week later, I read her my list. They are traits the women in my life possess (strength, kindness, positivity) and lack (realism, ambition, passion). “We can learn from the strong women around us,” says Annie, “but it doesn’t necessarily keep us from making their same mistakes.” She must see me deflating, because she quickly reminds me that I did finally end that bad relationship and I did walk away from a negative friend, so I’m learning. And that feels unspeakably good. $50/30min session

As I sit journaling later (more homework), I realize I’ve made more strides in an hour with Annie than the hundreds of texts to faceless therapists that came before her. Maybe I’m just a millennial who’s almost over the hill, but I need to look into someone’s eyes and face my demons, not throw them into a digital abyss. So I’ll keep opening up that Skype window to Annie—and the bonus is that I get to sit in my underwear while I do it.

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