I Followed My Friend's Unfiltered Advice For A Week And Here's What Happened

For most people, a guilty pleasure means making sure no one ever hears embarrassing 90s pop blasting from your headphones. Me? For most of my 20s, I harbored a secret addiction to self-help books. Just one look under my bed would reveal titles like You’re One Juice Cleanse Away From A Promotion and 300 Ways Not To Die Eating String Cheese Alone.

Guilty pleasure or not, my thirst for self-improvement will always be an intrinsic part of my personality. So when I heard about Freeform’s new show The Letter , in which a real group of friends is challenged to give each other unfiltered, anonymous letters of advice, I knew that I had to try it out for myself. I recruited two of my closest friends at work, Arielle and Stephan (who, coincidentally, I went to college with and have known for more than 10 years), to join me in this potentially awkward but enticing experiment.

Luckily, they agreed, and we made a pact to follow the rules of The Letter to the letter. After all, we each knew we had room for improvement — the question was whether our friends would tell us something totally unexpected, something we didn't want to hear.

We drew each other's names and anonymously wrote the selected person an honest letter, confessing what behaviors they need to change in order to better their lives. So how’d it go? Just how vulnerable were we willing to get? Are we still even talking to each other anymore? Follow our journeys below, in which we detail the Letters we received, our week carrying out its advice, and the lessons we’re taking away from the experience. And don't miss the series premiere of The Letter Tuesday, October 11th at 9/8c on Freeform.

The Letters

Anna: The Insomniac

The three of us drew names out of a bowl and wrote brutally honest (but loving) Letters to each other, which is harder than it sounds! Despite being initially afraid to open my Letter, my anxiety dissipated once I read it. Clearly written by someone who not only loved me but was sympathetic to my vulnerabilities, the author led with a list of my better qualities — then quickly got real.

The first challenge was a strict, military-grade sleep routine: electronics off at 9:30 p.m. followed by 15 minutes of meditation, and being in bed with a book by 10 p.m. — all meant to combat my frequent insomnia and anxiety. While my friends and coworkers have been outwardly sympathetic, the writer destroyed my delusion that my sleep issues don’t affect others, writing, “You’re late for work and it can be really frustrating for us.”

The second challenge was to stop saying negative things about myself for a week. Each time I slipped up, I would have to later buy my Letter Writer a drink. This was a huge challenge because my native tongue is self-deprecation — I have a habit of insulting myself before anyone else can. But drinks in New York City are expensive, and I was going to have to do anything I could to avoid purchasing this mystery person a $12 beer for every time I said something like, “I'm great second wife material."

Stephan: The Writer Who Doesn't Write

My Letter came at the perfect time. I'm not myself when I'm feeling creatively uninspired, and my Letter Writer must have noticed — and she must have psychic tendencies, too, because she called me out for “slacking" on my novel. I’ve been talking about my novel-in-the-making for a long time, and when people ask me how it's going, I always say I'm making progress, even if I'm not. As years have passed and I'm still not done, I think the people closest to me have put together that I must be creatively blocked.

At one point, I had crazy dreams of having published my debut by age 25, a deadline I’ve blown by a couple years. So many things happened in that time, like my career, sordid love affairs, etc. I’ve been busy!

But those are excuses. What’s actually been holding me back is this fear that I’m not up to the challenge, and that this novel won’t be the perfect classic that I envisioned it would be. After all these years, my Letter Writer finally inspired me to silence my own critic and find a way to get it done. Instead of just trying to jump in and try to barrel my way through an entire novel, my Letter Writer encouraged me to take baby steps toward "unblocking my creativity" first: Start writing honestly in a journal, and seek outside inspiration. That sounded doable to me, and I was ready to start taking real action.

Arielle: The Over-Apologizer

When I read my Letter, I had equal feelings of fondness for the person who wrote this, and dread at carrying out the tasks. I work with both Stephan and Anna very closely, but I couldn’t tell who the sneaky author was. There were plenty of sweet things that made me feel great about myself (“you glow so bright that sometimes, your light gets in people’s eyes”) but just as many “check yourself” tidbits. Whoever the author was (they described themselves only as “a person with a race and a gender”), they really had my number.

My first challenge was a doozy — I couldn’t say “sorry” for the whole week. If you’re like me, saying “sorry” is like oxygen for your guilty soul. Plenty of this has to do with being a young woman (and being conditioned to say sorry), but I use "sorry" for everything: moving past strangers on the street, asking for someone’s attention, bumping into inanimate objects.

Secondly, I had to approach three men in public — with no help from an app — and start a conversation. One would be at a party, one at a bar, and one at a location of my choice. I’m used to being open on the Internet, but opening up to new people in the unmediated wilds of public spaces is another story. As my special author put it, the exercise wasn’t about finding a love connection, but rather putting myself out there. I’ve also talked to men in bars before, so part of me was like, "I can do this."

The Experiment In Action

Anna's Week

The author of my letter outlined my sleeping regime’s details so meticulously that despite how complex the ritual was, it was easy enough to carry out. The problem: The week of the experiment came at an awkward time, as I was on vacation in Texas for a wedding. Sleeping on a friend’s sofa does not make for the best environment to practice a highly advanced sleep therapy program.

But rules are rules. In order to shut off all of my electronic devices by 9:30pm, we would have to leave social events awkwardly early, something I was reluctant to do. I must confess that I actually failed to get in bed by my prescribed bedtime of 10:30 p.m. twice during the week due to social commitments, but even those nights I still managed to be asleep before midnight—something previously unheard of. For once I was frustrating people with my early bedtime.

As for not saying anything negative about myself, this task was much harder to carry out because it was nowhere near as black-and-white as my sleep challenge, and self-deprecation is a much more deep-rooted part of my personality than I previously knew. In fact, I ended up slipping up nine times. That’s nine NYC-priced drinks that I owed the mystery Letter Writer.

What became especially difficult was catching the more seemingly innocuous negativity, such as the following statement:

Does saying you “feel” a certain way make it a negative statement? I decided that it probably did, so I made another tally mark, and then forcefully made myself say aloud something positive: “I am feeling very creative today.”

Stephan's Week

To make sure I succeeded in following the Letter Writer's advice, I did something I’d been avoiding for years: I bought a self-help book called The Artist’s Way , which so many successful creative people have recommended over the years. I always assumed it was too New Age-y for my tastes. One of the book’s philosophies is that if you’re creatively blocked, your Inner Artist, which is an innocent child, needs to be healed — it has been wounded over time by self-doubt and criticism.

I told you it was New Age-y. But there’s a totally valid point there. One of the reasons I freeze when I sit down to write my novel is that I have such negativity running through my head. You don’t have what it takes to write a whole novel. It’ll never turn out the way you’re hoping. My Inner Artist was in serious need of healing.

To silence that negativity, the book suggests something called Morning Pages. Every day, without fail, you’re supposed to roll out of bed and write three pages by hand — this just happened to fit perfectly with my Letter Writer's advice to keep a journal. Your writing doesn’t have to be good or interesting. Just spill every boring or self-critical thought on paper so it doesn’t fester in your head.

I bought a super-cool journal to help inspire me to stick to my Morning Pages because I’m a firm believer that beautiful tools help you stick to any task. Sure enough, I stuck to Morning Pages all seven days of the experiment, and it left me with a clearer head and more confidence when it came to my real writing. In addition to all my morning ramblings, I wrote 2,128 words of my novel. It doesn’t seem like much, but it’s a quality 2,128 words, and it's more than I’ve written in the past two months!

Arielle's Week

Surprise, surprise! Not saying “sorry” was hard. I felt myself wanting to say it all the time, either for bumping into someone on the subway, or for not being perfect at work. At first I felt a bit like a jerk, but this feeling dissolved the more I kept to my practice. Let other people do the apologizing for once. Look, Mom! I’m becoming an alpha!

Operation “talk to men” was just as tough. For the party dude, I spoke to a nice, handsome Colombian gentleman at a screening for a TV show, and he happened to be in it. Our conversation didn’t go too far, ‘cause we didn’t have much in common, but I was proud of myself for initiating.

I went out with a couple friends on Saturday night and spoke to two French guys at a pub, fulfilling my “bar dude” quota. We chatted for a couple minutes, but keeping the conversation going wasn’t easy. I should probably have expanded my pool to American men.

Sadly, the final challenge of approaching a wild card dude proved to be too difficult. I toyed with the idea of doing it in the subway. I considered a supermarket meet-cute. That’s how people met their spouses before apps, right? Ultimately, starting a spontaneous conversation with a cute random proved to be too intimidating, even off of my “not sorry” high.

Our Final Thoughts


In only seven days, the combination of more sleep and "forced" positivity produced major results. I was so much more productive and alert at work and surprisingly, even the quality of my work increased, in large part due to my more positive mindset. Arielle's prescription of New Age-y advice and tough love was just what I needed ... although our relationship is somewhat more complicated now that I owe her nine drinks.


Throughout the week, the journaling and newfound discipline combined to create what I call an “atmosphere of growth” — I truly felt the honest scribbles I was making in my journal put my mind in the present and quieted a lot of my self doubts. Thanks to my Letter Writer — who, no surprise, turned out to be Anna, who's been hearing about this not-yet-existent novel for 10 years — I feel a giant creative boost. Plus, I feel generally more energized, happier, and more inspired.


As it turns out, the person "with a race and a gender" who wrote my Letter was Stephan! And he was spot-on: My week of “not sorry” was a transformative experience. All week, I was allowing myself to be heard more clearly, and I'm ready to keep going with it. Bring on the unapologetic living!

Even if I didn’t fulfill my duties with the dude challenge, I felt like the practice shed a serious light on how I operate when talking to straight men. After this, I’m inspired to truly open myself up to meeting people without an end goal in mind. Instead, I just want to get to know more humans — whether platonic or romantic.

All three of us loved participating in our own Letter experiment and can't wait to watch the show! Check out the series premiere of The Letter Tuesday, October 11th at 9/8c on Freeform, and click here to try your own experiment!