Ask a Smart Person: An Interview with Entertainment Writer Bex Sinden

The exhausted-social-worker-turned-"Obsessed!"-entertainment-writer, talks about writing, reinvention, and our mutual weird fascination with Pete Davidson

As a newish Substack author, I have been reading a lot of newsletters. Bex Sinden’s Obsessed! was one of the first that stood out to me, not only for its content, but engaging voice, sense of humor, and great writing. We started talking and learned that we were both undergoing major life renovations¹, so I asked for an interview.

“Reinvention sounds exhilarating, and sometimes it is, but mostly it’s lonely and terrifying….I have to summon self-belief and self-motivation daily.”

BETH: So, we met virtually in a group for Substack writers and noticed that we were both reinventing our lives in this very weird time. Tell me about the path that led you to create your Obsessed! newsletter. 

BEX: I am so glad we connected! It feels strange to say this out loud, but professional burnout led to the creation of my newsletter. Seriously. I have been a full-time social worker² for twenty years, and in April 2021, I hit a wall. I took some time off to reflect, and I decided that I needed even more time to figure out if I could continue to do that essential work. I asked for a year off - unpaid - and my request was accepted. 

For the first time in my adult life, I had the time and the confidence to focus on my other love—entertainment reporting. I have always been a celebrity enthusiast (a term I coined to make my obsessions seem more mature). My friends and coworkers have relied on me for celebrity updates, hot takes, and viewing recommendations. I initially thought that I would start a podcast or a YouTube channel, but the production around those mediums felt too daunting. So I decided to turn to a medium I abandoned long ago, writing. Earlier in life, I had planned on becoming a writer, but I took some sociology courses while studying English literature at university and felt called to follow that path³. The creation of my newsletter, Obsessed! felt like a good way to revisit my early loves, entertainment and writing.

Sinden with Jennifer Lopez at the Toronto International Film Festival (TIFF) in 2019

BETH: I'm going to limit myself to asking just two questions about some of the topics you've written about. The first piece of yours that I read was the one about the obnoxiously hot Fashion Santa, himself a reinvention project. It was a great article, the kind of entertainment writing that I love to read even if I never actually encounter the subject—film, series, book, etc⁴. Do you have entertainment writers you love to read? I saw that you'd quoted the wonderful Owen Glieberman. What makes great entertainment writing? 

Sinden, right, with Fashion Santa at a fundraising event

BEX: Thank you so much! I am so proud of my piece about Fashion Santa. He was the perfect person for my first interview: interesting, inspiring, and hot.

My focus has often been on television entertainment journalists, and I am embarrassed to admit that I only recently started paying attention to the names of the people who write for my favorite magazines! SHAME ON ME! I love writers who do deep dives into the psyches of celebrities. For example, Michael Shulman recently wrote that astounding profile of Succession’s Jeremy Strong for The New Yorker. I love that kind of writing!

[Beth interjects an enthusiastic endorsement for that article!]

I discovered some of my favorite entertainment commentators—Evan Ross Katz, Fran Tirado, Samantha Irby, and Ira Madison—on Twitter and Instagram. They have magazine writing credits, television writing credits, and Tirado, Irby, and Madison have Substack newsletters. They are all queer, brilliant, witty, and socially conscious writers who are also unabashed celebrity enthusiasts. I enjoy entertainment writing infused with the writer’s personality, observations, and opinions. I also enjoy reading how writers feel when they interview a celeb, watch a show, or listen to music.

BETH: I love your hilarious obsession with Pete Davidson. But I have to say that I was a little bit disappointed in him for choosing Kim K. I'm laughing at myself when I say that I thought he had higher standards. You've analyzed what women see in him. What do you think he looks for in women? 

BEX: Many of my readers are hot for Pete Davidson, and I am obsessed with teasing them about it. I personally don’t share the attraction at all, but I am intrigued by him. I admire his tenacity, fun-loving spirit, and openness about his mental health. On the surface, Pete seems to gravitate towards gorgeous and successful brunettes. But I think he is looking for a deep emotional connection and someone to provide mutual care.

Pete has a trauma history (oh god, here comes my inner social worker), so it makes sense to me that he dated Ariana Grande shortly after the bombing at her Manchester concert. I think that many people forget that a few years ago, Kim Kardashian was robbed in her Paris hotel room, tied up, and held at gunpoint, leaving her with a trauma history. And who knows what she saw and endured while Ye went through his depressive and manic episodes! So Pete needs someone who empathizes with his past pain and understands his mental health struggles while striving for a fun and positive future.

BETH: But back to the topic!⁵ My newsletter is called The Next Thing because it's about the weird experience of trying to reinvent my life as a middle-aged BoomXer (I was born at either the end of the Baby Boom or the beginning of Gen-X, depending on how you count). In a perfect world, where is your Obsessed! project and where are you as an entertainment writer five years from now?

BEX: I hope that Obsessed! will continue to grow and evolve and that in five years, I will still be writing it as a love letter to my subscribers. I enjoy entertaining them, making them laugh, and making them think about pop culture in unique ways.

Beyond that, I see myself as an entertainment writer working for magazines like Variety, The Hollywood Reporter, The Cut, and Interview Magazine. As an Award Season fanatic, I would love to cover The Oscars and all of the red carpet events. I’d also be more than happy to have a talk show host gig. I love The Talk, and I dream about being one of their future co-hosts!⁶

This past summer, I participated in a self-development course. The facilitator guided us through an exercise and asked us to envision what we would be doing in five years. I immediately saw myself at a restaurant in Los Angeles, getting ready to sit down to interview a celebrity for a magazine piece. I was excited, happy, and at ease. I don’t know who the celebrity was but in the spirit of manifesting, I will say it was Lady Gaga. I LOVE HER!

Sinden connects with Lady Gaga at a TIFF event for A Star is Born in 2018.

BETH: What have you learned from your adventures in reinvention that you’ve found valuable?

Reinvention sounds exhilarating, and sometimes it is, but mostly it’s lonely and terrifying. So many people in my life are invested in who I have been for the past twenty years, and my decision to make dynamic changes is not necessarily celebrated. I have a few beloved cheerleaders, but I have to summon self-belief and self-motivation daily. I am living on savings I acquired through the sale of a home, and I do not have a current income stream. Everything I am doing is a risk, and no one is more aware of that than I am. That’s the lonely part. The exciting part is that I wake up every day knowing that I have finally made room for the part of myself that I abandoned twenty years ago—the wildly enthusiastic, creative being who has an awful lot to say about pop culture. 

Check out Bex Sinden’s newsletter Obsessed! on Substack!

1. When I wrote this, I was envisioning a home reno like the ones on HGTV that involve safety glasses, sledge hammers, and karate kicks. I think that metaphor only works if we acknowledge the fact that the part between gleeful demolition and sparkling reveal is much longer, dustier, and more expensive than it looks on TV.

2. Bex is actually the third fried social worker I know who’s hit that wall and their shift to entertainment writing isn’t even the most surprising plot twist. In chronological order, the first became a hair stylist and the second became a roofer. We need social workers, y’all. Maybe we should consider trying to make their jobs more bearable?

3. Neatly demonstrating English Lit profs’ article of faith that the discipline in particular and Humanities in general make us more empathetic and compassionate humans….

4. I am embarrassed to admit how often I do this. I subscribe to the New Yorker, where Arts and Entertainment essays and reviews are their own art form in the hands of writers like Anthony Lane, Doreen St. Felix, Emily Nussbaum, Jia Tolentino, Kelefa Sanneh, Hua Hsu, and many more. Lest we forget, Shakespeare’s plays were considered pop-culture crap unworthy of inclusion in libraries during his lifetime. We dismiss this genre as unserious or lightweight at our own historical peril.

5. I hope everyone appreciates the self-discipline I exercised here in not fangirling out over Bex’s celebrity encounters and articles. Obsessed! is packed with tempting little gems that will make you want to ask about three thousand follow-up questions. I mean, look at that picture of J. Lo. Does she even have pores? What was she like in real life?

6. Bex later added “I was giggling to myself about my bold dreams about someday writing for major magazines and co-hosting The Talk without taking a single journalism course! I like to dream big, but I do not have a big ego! I recently registered for a freelance journalism course through the University of British Columbia, and I will start it next week. After that, I might apply for journalism school as a next step if I like it. I believe that anything is possible, so I will keep working on my craft and dreaming big!”