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TLDRI: If I Could Sing I’d Be Unbearable with Drew Burnett Gregory

April 1, 2026·29 min·2 clips

Drew Burnett Gregory reveals how he's grappling with loving himself after facial feminization surgery.

1. Best Gabe Ever presents TLGRI, a Reddit-reaction show format, with guest Drew Burnett Gregory, a writer and filmmaker. 2. Drew Burnett Gregory is a trans writer and filmmaker who appeared on the previous week's episode and returns for this Reddit-focused format. 3. The episode's loose through-line is how people present themselves — in obituaries, online as beauty influencers, and through surgical and digital self-modification — and what those choices reveal about beauty standards and identity. 4. The first subreddit, Our Salty Obituaries, features 'brutally honest obituaries about not so great people'; Gabe reads one for Florence Flo Harrelson, 65, of Chelsea, Massachusetts, who died February 22, 2024, with the writer framing it explicitly as 'a public service announcement' because the deceased 'wanted those she terrorized to still be living in fear.' 5. The obituary was featured on Boston Public Radio and in a People Magazine collage of unusual obituaries; commenters noted the deceased's brother appeared on the TV show Maine Cabin Masters. 6. Gabe and Drew discuss the morality of hostile obituaries, with Gabe noting satisfaction from posts describing child abusers and sexual assault perpetrators and Drew expressing residual sympathy for complicated people while quoting Taylor Swift: 'I bury hatchets but I keep maps of where I put them.' 7. The second subreddit covers an Asian beauty influencer on Douyin (Chinese TikTok equivalent) who lost over 140,000 followers when a filter glitched live, revealing she looked nothing like her heavily filtered persona — described as 'paper white, big-eyed, anime doll.' 8. Gabe and Drew note that irony runs through the comments: most followers who left were men, many observers point out she is described as genuinely beautiful without the filter, and internet literacy problems allow some viewers to believe ultra-filtered images are real. 9. Drew frames the filter question as less about individual responsibility and more about navigating an already distorted beauty culture, drawing a parallel to wearing full makeup on a morning show versus using a digital freckle filter — both are image manipulation, one more accepted only because it is older. 10. Drew discloses that while at Buzzfeed they edited themselves thinner in photos, and that in the two weeks before top surgery they edited themselves flat in images — a practice they now describe as tied into trans experience and 'really complicated.' 11. Drew describes recent facial feminization surgery on the upper part of their face as leaving them unsatisfied with results, and articulates the pre-surgical framework: change only what 'feels other from you,' and try to love what 'feels like you but you sometimes hate.' 12. A year post-FFS, Drew is questioning whether the framework held, wondering if passing better would have been worth changing the jaw or the nose — features they deliberately chose to preserve. 13. Gabe introduces a parallel experience of being photographed at activism events: proud of the work but startled by candid photos, and noting that photos Elise (Drew's partner) loves most of Drew are precisely the ones Drew dislikes, and vice versa. 14. Drew reflects that the photo their partner finds most beautiful is probably one that captures authentic personality, while the photos they love of their partner are ones where the partner feels they 'look horrible' — the gap between self-perception and how one is loved. 15. The third subreddit post asks for hobbies suited to someone with a self-reported IQ of 83 and poor fine motor skills; Gabe and Drew question the validity of IQ as a metric, citing the Jamie Loftus podcast My Year in Mensa as evidence that IQ testing is associated with elitist gatekeeping. 16. Gabe recounts that his middle school split students into four classes labeled A through D and that students quickly decoded the ranking, an experience he describes as 'fucked up' for creating lasting self-assessments and hierarchies among peers. 17. Drew notes that their sister, who has ADHD and was told her whole life she was not smart, now runs a restaurant with skills Drew could not replicate — an example of how intelligence is domain-specific and IQ testing obscures it. 18. Hobby suggestions from the thread and the hosts include jigsaw puzzles, abstract painting, baking (praised for producing a tangible end product), and coloring books, with Drew noting fibromyalgia limits hand use. 19. The tone is casual, emotionally open, and frequently digressive; Drew's disclosures about surgery and body image give the episode a more personal register than typical Reddit-reaction fare. 20. People interested in trans perspectives on body image and beauty standards, or fans of unscripted personal conversation with Reddit-thread framing, will get the most from this episode.

As heard by us

A loose, funny conversation that keeps slipping toward something more honest.

The episode starts with a dumb, vivid joke about scuba diving to the bottom of the ocean and finding dinosaurs, then wanders into beauty standards, filters, AI, money, and the strain of feeling okay in your own skin.

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Why you'd press play

Play this if you want banter that turns weirdly sincere without warning.

Read the full recommendation in PlayNext →

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