Drag queen icon <a href="https://www.instagram.com/hereisbosco/?hl=en" rel="noopener noreferrer" target="_blank">Bosco</a> (Drag Race S14, All Stars S10) makes her return to toss even more shade. She shares why the secret to polished drag is having mean friends, how to filter out dumb men in your dating life, and trades stories with Nicole about their most questionable fashion eras. They also discuss facial feminization surgery (and the boy queens getting it) and why we all need some more razzle dazzle in our lives. Plus, Nicole has become a human white noise machine for the nice man in her life.See Bosco on tour! Get tickets at <a href="https://www.dragfans.com/bosco-tour-2026/" rel="noopener noreferrer" target="_blank">dragfans.com</a>. Buy 2 tickets, get the 3rd free. The whole polycule can come!Check out Bosco's new Magic The Gathering show, <a href="https://www.youtube.com/@SpellSlayers" rel="noopener noreferrer" target="_blank">Spell Slayers</a> on YouTube.Watch this episode on our YouTube channel at <a href="https://www.youtube.com/@WhyWontYouDateMePodcast" rel="noopener noreferrer" target="_blank">https://www.youtube.com/@WhyWontYouDateMePodcast</a>Support this podcast by checking out our sponsors:• <a href="http://WarbyParker.com/DATEME" rel="noopener noreferrer" target="_blank">Warby Parker</a>: Our listeners can buy one prescription pair and get 20% off any additional pairs at <a href="http://WarbyParker.com/DATEME" rel="noopener noreferrer" target="_blank">WarbyParker.com/DATEME</a> — and using our link helps support the show. #WarbyParker #ad• <a href="http://Chime.com/DATEME" rel="noopener noreferrer" target="_blank">Chime</a>: Chime is not just smarter banking, it is the most rewarding way to bank. Join the millions who are already banking fee free today. Head to <a href="http://Chime.com/DATEME" rel="noopener noreferrer" target="_blank">Chime.com/DATEME</a>.• <a href="http://squarespace.com/DATEME" rel="noopener noreferrer" target="_blank">Squarespace</a>: Head to <a href="http://squarespace.com/DATEME" rel="noopener noreferrer" target="_blank">squarespace.com/DATEME</a> to save 10% off your first purchase of a website or domain using code DATEME.• <a href="http://Audible.com/headswillrollseries" rel="noopener noreferrer" target="_blank">Audible</a>: Listen to Heads Will Roll: Heir Apparent, available now on Audible. Go to <a href="http://Audible.com/headswillrollseries" rel="noopener noreferrer" target="_blank">Audible.com/headswillrollseries</a> to start listening today.Check out all of our sponsors and discount codes at <a href="http://wwydm.notion.site/sponsors" rel="noopener noreferrer" target="_blank">wwydm.notion.site/sponsors</a>.Follow:All Links: <a href="https://linktr.ee/whywontyoudateme" rel="noopener noreferrer" target="_blank">linktr.ee/whywontyoudateme</a>Tour Dates: <a href="http://linktr.ee/nicolebyerwastaken" rel="noopener noreferrer" target="_blank">linktr.ee/nicolebyerwastaken</a>YouTube: <a href="https://www.youtube.com/@WhyWontYouDateMePodcast" rel="noopener noreferrer" target="_blank">@WhyWontYouDateMePodcast</a>TikTok: <a href="https://www.tiktok.com/@whywontyoudatemepod" rel="noopener noreferrer" target="_blank">@whywontyoudatemepod</a>&nbsp;Instagram: <a href="https://www.instagram.com/nicolebyer/" rel="noopener noreferrer" target="_blank">@nicolebyer</a>X: <a href="https://twitter.com/nicolebyer?lang=en" rel="noopener noreferrer" target="_blank">@nicolebyer</a>This is a <a href="https://headgum.com/" rel="noopener noreferrer" target="_blank">Headgum</a> podcast. Advertise on <a href="https://gumball.fm/shows/why-wont-you-date-me-with-nicole-byer" rel="noopener noreferrer" target="_blank">Why Won't You Date Me?</a> via <a href="http://gumball.fm/" rel="noopener noreferrer" target="_blank">Gumball.fm</a>.See Privacy Policy at <a href="https://art19.com/privacy" rel="noopener noreferrer" target="_blank">https://art19.com/privacy</a> and California Privacy Notice at <a href="https://art19.com/privacy#do-not-sell-my-info" rel="noopener noreferrer" target="_blank">https://art19.com/privacy#do-not-sell-my-info</a>.

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