Age Gap Dating Confessions

Picking up where we left off on the journey through my party girl past...in 2018, after my now-infamous Katz’s Deli bottom-outing incident, I moved to LA for 3 months and experimented with Cali Sobriety. It was…wild, and definitely nowhere near sober! When the pandemic came, I explored PROPER sobriety, and it taught me so much about my ADHD and ability (or lack thereof) to self-regulate and soothe. In fact, it completely changed my life. I dive into how ‘raw dogging reality’ has gotten me back in touch with my inner child; my stance on hallucinogenics as alcohol replacement; dealing with dating, sex, and general peer pressure while sober; and finally, where I stand with alcohol (and partying as a whole) currently. ~ Physique 57 literally transformed my body in only 8 classes. Use my code TABOO to save $10 on your On Demand monthly membership - plus you can start with a 14-day FREE trial. Code applied automatically at checkout. Click here: ⁠⁠⁠⁠⁠https://ondemand.physique57.com/orders/customer_info?o=80200&d=TABOO⁠⁠⁠⁠⁠  ~ Love letters? Hate mail? Share your thoughts at [email protected]. Follow Ali on Instagram & TikTok @aliweissworld. Tales of Taboo is produced and narrated by Ali Weiss. Audio production by Wolf Taylor & Aamir Augustine at WTF Media. Theme song by Chris Stathopolous. Cover photo by Erika Flynn. Cover art by Kristen Montenegro. "Degenerate" sweatshirts & G-Strings are available on Ali's Instagram via DM. --- Support this podcast: https://podcasters.spotify.com/pod/show/talesoftaboo/support

Gossip Girl, here - your one and only source into the scandalous lives of Manhattan's elite...no, but actually. If you've ever wondered what it was like to grow up in New York City, you've come to the right place. We're foraying DEEP into my party girl past over the next 2 weeks, and for part 1, let's throw it back to 2008-2011: the golden years of Jeffrey Campbells, tabloid mayhem, Indie Sleaze, Gossip Girl, and - how lucky was I? - Ali in high school. Starting from my very first memory of getting drunk (at my own chaperoned house party, iconic), and weaving through hookah bars, warehouses in pre-gentrified Brooklyn, rooftops, Meatpacking District clubs, teen charity galas, raves, and the best electronic music festival in North America, I'm revisiting every step of my burgeoning obsession with nightlife - and getting f*cked up... Then, because all pleasure comes with pain, we'll grin and bear my college years, where I drowned under depression and bottom-shelf liquor, threw Playboy Mansion-themed parties, studied abroad in London, and started thinking about getting sober... And we'll end 5 years later, at the moment I blacked out in Katz's Deli eating a pastrami sandwich - and decided to move to LA to finally experiment with "Cali Sobriety." Part 2 next week! ~ Magic Mind is an amazing replacement for both coffee and Adderall (either prescription or not), and has completely changed my relationship to caffeine. Go to https://www.magicmind.com/talesoftaboo and for the next 10 days, get up to 50% off your first subscription and 20% off a one-time purchase with my code TABOO. ~ Physique 57 literally transformed my body in only 8 classes. Use my code TABOO to save $10 on your On Demand monthly membership - plus you can start with a 14-day FREE trial. Code applied automatically at checkout. Click here: ⁠⁠⁠⁠https://ondemand.physique57.com/orders/customer_info?o=80200&d=TABOO⁠⁠⁠⁠  ~ Love letters? Hate mail? Share your thoughts at [email protected]. Follow Ali on Instagram & TikTok @aliweissworld. Tales of Taboo is produced and narrated by Ali Weiss. Audio production by Wolf Taylor & Aamir Augustine at WTF Media. Theme song by Chris Stathopolous. Cover photo by Erika Flynn. Cover art by Kristen Montenegro. "Degenerate" sweatshirts & G-Strings are available on Ali's Instagram via DM. --- Support this podcast: https://podcasters.spotify.com/pod/show/talesoftaboo/support

I've been getting a lot of feedback on Instagram (mostly from far-right men, duh) about how it's "embarrassing" and "pathetic" that I've admitted to sometimes still feeling like a teenager at 30. Not only does a husband, child, and home ownership sound deeply unappealing to me right now, but I don't think those things actually constitute an "adult." I know I can't be the only person out there who isn't following, and doesn't necessarily want to follow, all of society's guidelines for how to correctly "grow up." In pursuit of defining what the f*ck adulthood even means, I get extremely candid about living with my parents until I was 28, and now living with 2 roommates (my ex-boyfriend & gay best friend); working my way up to a 6 figure salary but mismanaging all of my money (and then losing my job); actively growing apart from some friends and closer to others as everyone's path starts to diverge with marriage and children; and my new relationship, which I'm so happy in but have deliberately NOT centered around the idea of "settling down." ~ Physique 57 literally transformed my body in only 8 classes. Use my code TABOO to save $10 on your On Demand monthly membership - plus you can start with a 14-day free trial! Code applied automatically at checkout. Click here: ⁠⁠https://ondemand.physique57.com/orders/customer_info?o=80200&d=TABOO⁠⁠  ~ Share your own confession - or love letters and hate mail - at [email protected]. Follow Ali on Instagram & TikTok @aliweissworld. Tales of Taboo is produced and narrated by Ali Weiss. Audio production by Wolf Taylor & Aamir Augustine at WTF Media. Theme song by Chris Stathopolous. Cover photo by Erika Flynn. Cover art by Kristen Montenegro. "Degenerate" sweatshirts & G-Strings are available on Ali's Instagram via DM. --- Support this podcast: https://podcasters.spotify.com/pod/show/talesoftaboo/support

In our sex-crazed, beauty-obsessed culture, why is it still so taboo for beautiful women to admit to CONSCIOUSLY (and shamelessly!) using their looks for personal, professional, and financial gain? The truth is, my appearance has been responsible for the majority of what I was able to achieve throughout my 20s — not just professionally as an on-air host, model (groan), and content creator, but in navigating a wide variety of global social scenes and subcultures, too. Though who I am as a person made the magic happen, the way I look always opened the door - for better or worse.  I have zero regrets, but at 30, I’m starting to focus more on developing the parts of myself that aren’t perceptible. To be looked at and *seen* is an immense privilege, but it also led to an over-dependence on the reaction I solicit from others - even outside of audition rooms or sound stages. In certain ways, it’s led to the dissolution of important emotional boundaries, too. (Like, why tf do I feel numb to sexual harassment?) The truth is, the things that make me feel truly SEXY have nothing to do with my face or body - they’re totally internal. And contrary to what society wants women to believe, most of them have come with age! ~ Vella’s Women’s Pleasure Serum is a pre-play lotion that makes it easier to have orgasms and makes orgasms more intense - and it's totally changed my relationship to sex. Use code TABOO20 for 20% off at vellabioscience.com. Use my code TABOO to save $10 on your On Demand monthly membership at Physique 57 - plus start with a 14-day free trial. Code applied automatically at checkout. Click here: ⁠https://ondemand.physique57.com/orders/customer_info?o=80200&d=TABOO⁠  ~ Share your own confession - or love letters and hate mail - at [email protected]. Follow Ali on Instagram & TikTok @aliweissworld. Tales of Taboo is produced and narrated by Ali Weiss. Audio production by Wolf Taylor & Aamir Augustine at WTF Media. Theme song by Chris Stathopolous. Cover photo by Erika Flynn. Cover art by Kristen Montenegro. "Degenerate" sweatshirts & G-Strings are available on Ali's Instagram via DM. --- Support this podcast: https://podcasters.spotify.com/pod/show/talesoftaboo/support

2 years ago, I found myself in perhaps the most taboo situation: unexpectedly pregnant, and making the subsequent decision to have a medical abortion. I was 28, in a happy relationship, and financially stable: from the outside people would say I was equipped to see, and “should have" seen, my pregnancy through. Emotionally, however, I was - and am - far from ready to be a mother. The decision to abort was easy; admitting to it publicly was not. In light of the ongoing battle over women's reproductive rights in America - and now, specifically, over the abortion pill - I've decided to re-release this episode. Many women in media, and throughout liberal areas of the country, are openly, vocally pro-choice; however, rarely (if ever) do those who’ve actually had an abortion shamelessly speak up about it. Of course I understand - no one, including myself, wants to be judged, attacked, or outcasted. But silence keeps the process misunderstood and stigmatized to the outsider, and deeply lonely for those who have gone through it. The pain of having nobody to talk to is far worse than the procedure itself. I don’t expect to change the world by telling my story, but maybe laughing and crying about it will give others the strength to speak out, too. At the least, I hope to comfort those who feel alone, confused, or afraid in their journeys, as I very much did mine.  ~ This episode is sponsored by Physique 57. Use my code TABOO to save $10 on your On Demand monthly membership - plus start with a 14-day free trial. Code applied automatically at checkout. Click here: https://ondemand.physique57.com/orders/customer_info?o=80200&d=TABOO  ~ Share your own confession - or love letters and hate mail - at [email protected]. Follow Ali on Instagram & TikTok @aliweissworld. Tales of Taboo is produced and narrated by Ali Weiss. Audio production by Wolf Taylor & Aamir Augustine at WTF Media. Theme song by Chris Stathopolous. Cover photo by Erika Flynn. Cover art by Kristen Montenegro. "Degenerate" sweatshirts & G-Strings are available on Ali's Instagram via DM. --- Support this podcast: https://podcasters.spotify.com/pod/show/talesoftaboo/support

I've noticed an increasing trend on social media, especially TikTok, where people are creating personal brands out of mental health struggles - specifically, ADHD, anxiety, and mood/behavioral disorders. Visibility is really important, but this approach rubs me the wrong way. When you have ADHD as an adult, it's rarely taken seriously - in fact, it's often glamorized, made the butt of jokes, or seen as an excuse for being lazy. In truth, ADHD and anxiety has kinda f*cked up my life, causing bouts of severe depression and stopping me from living up to my fullest potential. It's time to get real about what living with a 'disorder' looks like - well, at least through my mascara-ed eyes. Starting with a brutally honest list of my day-to-symptoms, we go deep into my complicated relationship to the word "crazy"; history with learning disabilities and mood disorders in school; bottoming out at college; the various coping mechanisms I developed over the years, including drugs and alcohol and developing an outlandish, hyper-confident persona; regrets I have about my past behavior and what I hope life will look like now that I’ve entered my 30s; and why Paris Hilton has become my unlikely mental health hero. ~ Share your own confession - or love letters and hate mail - at [email protected]. Follow Ali on Instagram & TikTok @aliweissworld. Tales of Taboo is produced and narrated by Ali Weiss. Audio production by Wolf Taylor & Aamir Augustine at WTF Media. Theme song by Chris Stathopolous. Cover photo by Erika Flynn. Cover art by Kristen Montenegro. "Degenerate" sweatshirts & G-Strings are available on Ali's Instagram via DM. --- Support this podcast: https://podcasters.spotify.com/pod/show/talesoftaboo/support

Welcome back to Tales of Taboo! I've been so inspired by the past 3 years of being a safe space for your unconventional and so-called 'unacceptable' confessions, that I feel compelled to spend Season 5 speaking solo and on-the-record about my own. To kick it off, we're talking about failing. Or rather, "failing." Going into 2023, I felt like I had it all: a great partner, a six-figure hosting career, and the best body of creative work I'd ever produced. Then, everything disappeared. At the time of recording this episode, I was unemployed, broke, and single at 30 - plus, I accidentally deleted all of my past confessions episodes from my records. For the past 6 months, I've quietly been back at Square One in so many ways. I get real about my physical sickness-level burnout, why Season 4 was cut short (and why I kinda resented it), and how my professional responsibilities bled into my personal life and made me disregard my own feelings. But losing my job & sense of joy led me to re-evaluate & re-build my boundaries, and now, I'm optimistic about the future. Other people might consider me a big fat f***ing failure, but I actually feel like I'm ahead in many ways - because I love myself (and all of my flaws and shortcomings) more than I ever have. ~ Share your own confession - or love letters and hate mail - at [email protected]. Follow Ali on Instagram & TikTok @aliweissworld. Tales of Taboo is produced and narrated by Ali Weiss. Audio production by Aamir Augustine at WTF Media. Theme song by Chris Stathopolous. Cover photo by Erika Flynn. Cover art by Kristen Montenegro. "Degenerate" sweatshirts & G-Strings are available on Ali's Instagram via DM. --- Support this podcast: https://podcasters.spotify.com/pod/show/talesoftaboo/support

The Fashion episode was such a hit that I decided to revamp and re-release another set of industry-related confessions. With casting help from DeuxMoi, we're coming out from behind the scenes and exploring life in front of the camera as a model. I open the episode with my own Tales of Taboo about my lulz attempt at a postgrad modeling career (you'll scream at the very off-brand national campaign I booked), and a few encounters with agents and casting directors that, as the kids say, 'altered my brain chemistry'. (10:50) Then, our anonymous contributors are or were signed in LA, London, Miami, Milan, New York, Paris, Seattle, and Texas, and represented by well-known agencies such as One Management, Genetics, Heffner, Next, Select, and Women (plus some others I’ve been asked not to name). They tell equally juicy and shocking stories about: -what it’s like behind the scenes at Fashion Week & Miami Swim Week  -working for controversial brands like American Apparel and Yeezy -lesser-known but higher paying sectors of the industry, like e-comm and fit modeling -the harsh realities of diet + exercise routines (maintaining 35 inch hips!!) -model houses, club promoters, and international ‘yachting’ trips -loneliness and depression brought on by working abroad -agency debt, and what success ACTUALLY looks like Plus, ON the record, we have agent Jane Belfry (@janebelfry) from BTWN Management breaking down the “body positivity movement” and model-turned-badass musician Dana Dentata (@danadentata) serving honest insight on everything from industry hyper-sexualization to working with icons like Ryan McGinley and Juergen Teller. ~ GOT A SECRET TO GET OFF YOUR CHEST? Share your own confession - or thoughts and feedback - at [email protected]. Follow Ali on Instagram & TikTok @aliweissworld. Tales of Taboo is produced and narrated by Ali Weiss. Audio production by Isabel McMahon & WTF Media. Theme song by Chris Stathopolous. Cover photo by Erika Flynn. Cover art by Kristen Montenegro. "Degenerate" sweatshirts & G-Strings are available on Ali's Instagram via DM. --- Support this podcast: https://podcasters.spotify.com/pod/show/talesoftaboo/support

Which famous designer refused to pay for $100,000 worth of samples? What major eyewear company has a Chief Financial Officer with no credentials besides being a party magician? Where does being over a size 6 and an A cup make you "fat?" What really happens behind the scenes at Fashion Week? I LOVE clothes. I love theatrics. I love escapism. What I do not love is when some people suffer greatly to compensate for others’ greed. On the heels of New York Fashion Week, I decided to revamp and re-release one of my juiciest, most scandalous, most shocking, and all-time favorite episodes. Our anonymous contributors went to hell and back in different parts of the exploitative, discriminatory, and deeply unglamorous Fashion Industry. With the help of DeuxMoi, I found ex-employees of American Eagle, BCBG, Dolce Vita, Halston, Free People, Linda Farrow, Stone Cold Fox, Victoria Beckham, Zac Posen, and some of the most famous- and infamous- fashion houses IN THE WORLD that I can’t mention by name! From dreamy, druggy parties to nightmare celebrity clients, body shaming to illicit sex, criminally low salaries and even lower self-esteem, turns out fashion is everything and nothing you thought it would be.  In the words of one of our confessors: “we’re paying countries and people literally no money because we [the consumer] need fashion. I don’t think people realize that.”  ~ GOT A SECRET TO GET OFF YOUR CHEST? Share your own confession - or thoughts and feedback - at [email protected]. Follow Ali on Instagram & TikTok @aliweissworld. Tales of Taboo is produced and narrated by Ali Weiss. Audio production by Isabel McMahon & WTF Media. Theme song by Chris Stathopolous. Cover photo by Erika Flynn. Cover art by Kristen Montenegro. "Degenerate" sweatshirts & G-Strings are available on Ali's Instagram via DM. --- Support this podcast: https://podcasters.spotify.com/pod/show/talesoftaboo/support

What do you think of when you think bisexuality? Promiscuous behavior? Polyamory? Lying, cheating spouses? Midlife crises? Burning Man? Or maybe you think of…nothing: perhaps the biggest misconception is that middle-of-the-spectrum sexual orientation doesn’t really exist. Au contraire, I believe that we’re ALL a little gay - some of us have just chosen, or found the freedom, to explore it. In honor of Bisexuality Awareness Week, I decided to revamp and re-release this legendary episode from season 3. After my own on-the-record confessions (sorry mom & dad), our (VERY NSFW) anonymous contributors recount discovering their sexuality in a myriad of ways, like hooking up with their staff, rendezvouses with strangers from Grindr, or deep in the trenches of Berlin nightlife. We also hear tidbits about the LA orthodox Jewish gay community - so cool - and Skirt Club, a now-infamous, all-female sex party specifically for bicurious women around the globe. Bisexuality doesn’t mean hypersexuality, though: for every story involving polyamory or threesomes, there’s one about choosing the comfort of a committed heterosexual relationship and wondering if it’ll be stifling in the long run. While some contributors deeply wish for acceptance from the LGBTQ community, others don’t feel the need to ‘prove themselves’. What they can all agree upon, however, is that bi-erasure and judgment - and a subsequent lack of identity - is real. As one of them so aptly said: “Hell is other people. Not because they inherently suck, but because their judgments rule how we act.” ~ GOT A SECRET TO GET OFF YOUR CHEST? Share your own confession - or thoughts and feedback - at [email protected]. Follow Ali on Instagram, TikTok, & Twitter @aliweissworld. Tales of Taboo is produced and narrated by Ali Weiss. Audio production by Isabel McMahon & WTF Media. Theme song by Chris Stathopolous. Cover photo by Erika Flynn. Cover art by Kristen Montenegro. "Degenerate" sweatshirts & G-Strings are available on Ali's Instagram via DM! --- Support this podcast: https://podcasters.spotify.com/pod/show/talesoftaboo/support