Jonah Feingold is a writer and director. Jonah recently premiered his first feature film "Dating & New York," which is available to watch in theaters and to stream now. Jonah and I start off by discussing how he and former guest Ilana Dunn ended up co-hosting the dating podcast "Seeing Other People." Afterwards, Jonah breaks down his new feature film and we discuss how he was able to push past the "nos" from Hollywood and forge his own path by making a movie without permission, landing him an amazing cast and IFC stamp of approval. We also get into the intricacies of dating as Jonah explains why dating has become such a topic of interest and something that has inspired him creatively. We finish up with a game of "mansplaining," where Jonah mansplains things that men (typically the heterosexual ones) do in relationships that confound women. This is a really special episode as it tackles a lot of interesting themes and is my first this season that really incorporates a male POV on dating. Follow Jonah @jonahfeingold and @datingandnewyork. Watch Dating & New York in theaters, on Apple TV, Amazon, and more by searching the title.

Eileen Kelly is a sexual educator and mental health advocate. Eileen and I discuss everything from how she started her iconic blog Killer and a Sweet Thang (KAAST) in her early teens, to how she launched her current podcast Going Mental with Eileen Kelly. Eileen opens up about how as her brand success grew, her mental health began to deteriorate in turn, causing her to check into the famous mental health hospital McLean. Together we discuss her time in McLean, the pros and cons of medication, the stigmatization of both sexual and mental health, and so much more. We finish off the episode with the segment “Quarter Life Qualms,” an examination of the 20s and her experiences as a 20-something, and a game of “7 Tea Questions,” 7 fun rapid-fire questions. Follow Eileen @eileen and @killerandasweetthang and listen to "Going Mental with Eileen Kelly" wherever you get your podcasts. Read her blog at https://killerandasweetthang.com/.

Sarah Levy is a writer and author. Sarah's work focuses on the intersection of sobriety, relationships, and identity and has appeared in The New York Times, The Cut, Cosmopolitan, Refinery29, The Washington Post, and more. Her debut novel Drinking Games will be out in early 2023. Sarah and I discuss why Sarah decided to get sober despite not having a clear cut drinking problem. She gets into her life before vs. after quitting drinking and how difficult it was for her initially to come out to her friends, family, and the people she was dating, but how when she eventually did it, it changed her life for the better. She is passionate about how her decision has bettered her energy levels, relationships, body image, and more-- as she says in the episode, “it’s like waking up in clean sheets every day.” We also get into how We Met at Acme podcast host Lindsey Metselaar introduced her to her now fiancé as well as her engagement story. Follow Sarah @sarahllevy and find her writing at https://www.sarahllevy.com/. 

Ilana Dunn is the host of the podcast “Seeing Other People”. We explore a range of topics together, starting with how Ilana’s time in the music industry and as Social Media Manager for Hinge prepared her for her current role as a dating podcaster. Next we get into Ilana’s dating life and how she realized that being open about her past dating experiences helped both her and the people taking in her content. Other themes we explore include how men and women approach dating differently; why it’s important to continue to make friends in your 20s and beyond; how society has glorified depression and negative self-talk; and so much more. This episode flows so naturally and is a fun look behind the curtains of the podcasting and dating worlds. Follow Ilana @ilana.dunn and her podcast Seeing Other People @seeingotherpeople.

Corey Rae is a wonderful activist, actress, consultant, model, producer, speaker, and writer. Corey tells her wild ride of a story, from transitioning from male to female at a very young age, to "going stealth" in college (AKA not disclosing her trans status), to living in LA as a vocal and proud woman and trans activist today. In particular, she touches on the experience of dating and details how dating as a female of trans experience can make an already complicated world even more complex. We then commiserate over the dating scene in LA, get into "Quarter Life Qualms," and play a rapid fire game of "7 Tea Questions." Follow Corey @imcoreyrae and check out her updated website at https://www.coreyrae.com/. 

Alessandra Torresani is a bubbly, brilliant, and brave actress and podcaster. Alessandra is extremely vulnerable and opens up about a variety of experiences she’s had, including her longtime career in acting as well as her experiences living with bipolar disorder. We break down the meaning and intricacies of having bipolar disorder, as Caitlin is familiar with the condition, and discuss how mental health should be seen as existing on a spectrum instead of as black and white diagnoses. Alessandra details how she withheld her diagnosis for years due to the fear of being stigmatized, and opens up about how she finally “came out” with her diagnosis. We then get into the Britney Spears conservatorship battle and explain how, while we are both team Britney and want what’s best for her, we both feel that there is probably more to the situation than the general public understands. We finish up with Quarter Life Qualms and a quick game of 7 Tea Questions. This episode is at once fun, informative, and deep, and definitely is one you don’t want to miss. Follow Alessandra @alessandratorresani and @emotionalsupportpod. Listen to the EmotionAL Support podcast on Apple, Spotify, or through her website ​​https://www.emotionalsupportpod.com/.

Usama Siddiquee is a Bengali-American comedian and actor. He has been featured in America's Got Talent, BET's 50 Central, Showtime's Desus and Mero, Netflix's Dash & Lily, and more. He's a regular in the NYC standup scene and frequently performs at venues like the Comedy Cellar and Caroline's. The interview starts out with Usama turning the tables on Caitlin and grilling her on her love life and her so-called “Southern drawl.” He then opens up about how he got into comedy instead of going to med school, his parents’ initial aversion to that decision, and the documentary that inspired him to live “inside out”-- AKA for himself and not external validation. We finish up the first section discussing his time on America’s Got Talent, where he made Simon Cowell laugh and offended Heidi Klum. During the Quarter Life Qualms segment, he discusses some of the differences between his 20s and 30s and the unique challenges our generation faces that boomers did not. We finish up with a rapid fire game of 7 Tea Questions. Follow Usama @usamastandsup and his podcast Mango Bae @yourmangobae. 

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Iman Hariri-Kia is the current Her Campus Deputy Editor and a longtime journalist. On her episode, Iman discusses how she transitioned from singing and songwriting into working as a writer and editor for a slew of amazing publications, including Teen Vogue, Bustle, Elite Daily, Man Repeller, and now Her Campus. We start out the conversation discussing her time writing and working in the Sex and Relationship space, and how her commitment to writing openly and vulnerably overrode any fears she had about disclosing information on her former sexual experiences. Iman also writes openly about mental health and relays how some of these articles, while initially difficult for her Iranian-American family, ended up opening up conversations that otherwise would never have existed. This episode delves into a lot, but some other topics include the political nature of hair, especially for women of color; how what you do should not define who you are; the dangers of fit and diet teas and how they contribute to disordered eating; and the importance of youth culture and why Gen Zs inspire Iman and her writing. Follow Iman @imanharirikia. 

Alice Bell is a full-time astrologer and writes for British Vogue as their resident astrologer. Her episode starts off season 2 of the podcast. Together, we break down some of the basics of astrology and answer listener questions on things like the sun/moon/rising signs' significance, what houses vs. planets are, and more. Alice talks about how astrology shifted her path in life and how it, in her words, "worked better than therapy." We move on to talk about the Saturn Return and its effect on us in our later 20s and she relays how it could be considered a version of a "quarter life qualm" or crisis. Finally, we finish up with a quick game of Myth Busters, where Alice either busts or confirms the truth of widespread assumptions about astrology. Follow Alice @stalkalice on Instagram, book a chart reading on her website https://stalkalice.com/, and listen to her cohost the "Astrology and You" podcast wherever you get your podcasts.

Case Kenny is a writer, podcaster, and recording artist with the wildly popular podcast "New Mindset, Who Dis?" Case discusses how he started his podcast and why he decided to get into mindfulness techniques, and later on, apply those techniques to dating. We start out by discussing who he was prior to these ventures, then get into a range of dating topics, including how to make single your superpower, why f*ckboys act the way they do, the importance of having a "why" for dating, and some of the ways we can get tripped up along the way. Next we get into quarter life qualms questions, where Case advises us all on how to achieve his level of groundedness, and then play a quick game where Case gives his take on dating clichés. Follow Case @case.kenny and listen to "New Mindset, Who Dis?" wherever you get your podcasts.

Paige Cole is one of the stars of season 8 of MTV's "Are You the One"-- the first ever season to feature an entirely queer cast. In the first half of our discussion, Paige and I get silly, drinking chardonnay and discussing all the risqué topics, ranging from her new strap-on to our thoughts on female masturbation. In the second half, we get deeper and more focused in discussing Paige's recent breakup with one of the show's costars (TRIGGER WARNING: abuse and suicidal thoughts discussed). We talk emotional abuse, relationship toxicity, co-dependency, reactive abuse, and healing after a traumatic relationship and breakup. We end the episode with a new segment called "fans who f*ck" where we answer all the lovely fan and listener questions we got for our girl Paige. Follow Paige on Instagram @paige_cole and watch AYTO S8. 

Dylan Hafer is a Betches Media writer, "Mention It All" Podcast Co-Host, and @bravobybetches creator. Dylan and I obviously mention it all-- that being all thing Bravo, from Housewives, to Summer House, to his craziest interview stories. However, Dylan also opens up about personal matters, such as struggling to find his path after college and navigating a long-distance relationship upon moving to a new city. We finish up with a new game called "Bravo Bravo Bravo," where I basically ask him every Bravo question I've been dying to since the creation of his @bravobybetches account. Don't miss out on this super fun episode and follow Dylan @dylanhafer and @bravobybetches and listen to him co-host the "Mention It All" podcast. 

Louis Levanti is a content creator and TikTok sensation. Louis and I connected when I saw his hilarious post on TikTok re: annoying things that he hates that may or may not make you a serial killer (milk drinkers, we're looking at you). Together we discuss Louis' new lease on confidence, soccer and other sports (believe it or not), body standards/ideals for men and women alike, crossing the line in comedy, reality competition shows, and so much more. Louis is one of my favorite guests and this episode is such an easy, fun listen-- be sure not to miss out! Follow Louis on all platforms @louislevanti 

Danielle Dietzek and Julie Griggs are co-founders of the double dating app Fourplay. Danielle and Julie have been best friends since their time at Penn State for undergrad and developed the app after having wild success from making a joint dating profile. From then on, they realized the perks of dating in pairs rather than one on one; safety, reduced awkardness/judgment/pressure, and more fun, to name a few. We also get into absurd tangents such as discussing Julie's alter-ego and my awkward misnomer for her, Jessica, singing and podcast jingles, why we stan Fauci, newborn baby problems, and so much more. Later in the podcast we go deeper and discuss eating disorders and the extremely special friendship that jump-started this app. Find Fourplay @fourplaysocial on Instagram and download the app at the App Store or Google Play.

@thefakerothko is a niche, humorous Instagram account with anonymous founders that come onto the pod as girl and boy Rothko. My friends and I have been following for their page for quite some time now, as it's wildly popular within the NYC and LA scenes. Boy and Girl Rothko open up about how they met, started their page, and some goals moving forward. We also rant about hypocrisy people have towards covid, Taylor Swift, the fascinating nature of privilege, where to draw the line in comedy vs. PC culture, and so much more. Don't miss out and follow @thefakerothko. 

Bryan Russell Smith is a writer, producer, content creator, and a cohost of the Betches Sup Podcast. Bryan and I discuss a whole range of topics, including but not limited to his transition from producing to starring in his videos for Betches and TikTok, the stress of the election as a political podcast cohost, his meet-cute with his current boyfriend, and so much more. We also discuss how we wish we could dance to all the 2020 bangers without worrying about our health, hence the title of the episode. Don't miss out on this episode and follow Bryan @bryanrussellsmith and The Betches Sup @betches_sup. Listen to The Betches Sup anywhere you get your podcasts. 

Elias Friedman is a photographer and the founder of The Dogist franchise (@thedogist). Elias talks about how he started The Dogist, his history as a dog photographer, his job prior to the Dogist, and how getting fired from said job ended up being the opportunity of a lifetime. We also discuss things such as BDE, AKA "big dog energy," the Team Dogist dog gang, our quarantine pups Elsa and Delilah, and so much more! Don't miss out on this Thanksgiving Special. Follow Elias @thedogist and @eliaswf 

Ashley Gavin is a comedian, actor, and the host of "We're Having Gay Sex" Podcast. Ashley and I have an amazingly fun and fluid (no pun intended) conversation, covering everything from gay sex, to how Ashley met her notoriously hot girlfriend, to blowing up on TikTok, and so much more! This episode was recorded around her birthday, so the episode is entitled "We're Having Gay Birthday Sex." We also get deep and discuss depression, loss, anxiety, and how to cope. Don't sleep on this stellar episode. Also follow Ashley @ashgavs on Instagram, Tiktok, and more. 

Dylan Palladino is an NYC based standup comedian, podcaster, and actor. Dylan and Caitlin get into everything from their first and last date, to the falling out afterwards, to Dylan's type and why he appreciates a good DM slide. We also discuss how Dylan got into comedy, whether men and women can successfully be "friends with benefits," what makes for a good thirst trap, Dylan's crisis moment in his 20s, and so much more! Be sure to follow Dylan @dylanjpalladino and listen to his podcast "We're All Psychos" wherever you get your podcasts. 

Tori and Leah are the founders of the Boys Lie clothing line. The ladies get super vulnerable and open with me about what "boys lie" means to them (it's not what you think- despite the name they don’t want to drag men), the story behind their friendship, and their shared heartbreak that they re-purposed into an up and coming streetwear clothing company. I start out by quickly addressing up top my week from hell and the toll that having Corona took on my body in mind. Then I get into it with the guests, discussing a range of topics including cheating (I in particular get very deep) and how to handle it, different types of "love" and relationships, my concussion story and how it affected how I initially felt about podcasts in general, juggling work-life with personal-life matters, and so much more! We end with a classic game of "what the fuckboi," AKA would you rather featuring all the fuckboi behavior. I can't wait for you to hear this episode-- it's really vulnerable and honestly a treat. Follow them @boyslie. 

Andrew "Puddles" Collin is a stand-up comedian and best friend to Nikki Glaser. Andrew starts out by bullying me on my own podcast just to show me who's boss because he has a lisp. We then get into a mixture of ridiculous topics in an absurd fashion, including but not limited to Nikki Glaser, his dog walking past, sobriety, how you can't unf*ck someone, therapy, and so much more. We end with a game of the classic "7 Tea Questions." Andrew even reminds you to "vote," he doesn't care who for. Get ready to laugh your ass off and share this episode with all your friends and rate, review, and subscribe. Follow Andrew @andrewtcollin, listen to his podcast Puddles with Andrew Collin wherever you get your podcasts. 

Carola is an acclaimed novelist and author of the book Tell Me Lies, which is a "thrilling, sexy A thrilling, sexy coming-of-age story exploring toxic love, ruthless ambition, and shocking betrayal, Tell Me Lies is about that one person who still haunts you—the other one. The wrong one. The one you couldn't let go of. The one you'll never forget." Carola was a huge get considering she just gave birth to son James and is a new mom. Luckily, however, she still had time to sit down with me and chat everything from toxic men, to on and off again "situationships," to eating disorders that take over your life; the whole nine yards really. Lucy, the novel's protagonist, is a college student who is caught up in the dual toxicity of her emotional draining "relationship" with master manipulator Stephen and her battle with a nasty eating disorder (which of course is only worsened by the situationship at hand). Carola stresses that while the novel is entirely fictional, it rings emotionally true to her and some of her past experiences with men and eating. This episode gets so deep and raw and is so incredibly important for women, let alone people, of all ages. Find Carola at @carolatlovering on Instagram and buy Tell Me Lies on Amazon at https://www.amazon.com/Tell-Me-Lies-Carola-Lovering/dp/1501169645 or at your local bookstore. Get ready for her second novel Too Good to Be True which is hitting bookstores March 2021.

Lindsey Metselaar is the host of We Met at Acme host and Lindsey's Lunchbox CEO. Lindsey barely needs any introduction considering We Met at Acme is one of the most iconic dating podcasts and helped inspire me to start this podcast. Lindsey and I get into a huge range of topics, including but not limited to growing up in NYC (and the ensuing Gossip Girl comparisons), Lindsey's current boyfriend and how they first met/kissed, horoscope signs, Saturn returns, her recent 30th birthday, sobriety, and more! It was so amazing to get to hear more about Lindsey and her experiences since she is usually in the interviewing seat, not the interviewee hot seat. I can't wait for you to hear this iconic episode and let me know what you think! Follow Lindsey @lindzmetz and @wemetatacme

Kate is the co-host of Hey, Beautiful! A #HIMYM Podcast, and most importantly viral sensation known as "Girl With a Microphone" for calling out Trump supporters pre-election. Kate chooses to keep her last name private as she is out there fighting the good fight, AKA going to Trump rallies in her local neighborhood and reminding the attendees that Trump is, in fact, "a literal demon from hell." Kate first went viral a few weeks ago and was considered by many, celebrity and otherwise, to be an "outstanding ally" for using her privilege for the greater good-- AKA working towards getting Trump out of office. We figured there was no better time to release this episode than on the week of the most insane presidential debate that anyone as ever witnessed. In addition to politics, Kate and I discuss her being gay and infidelity ("women lie too"), owning your standards in relationships, how she met her wife, and so much more! We finish up with a silly but deeply upsetting game called 10 Things I Hate About You: Trump Edition. Follow Kate on Instagram or TikTok @girlwithamicrophone. 

Kyle is an actor, Broadway and West End veteran who has performed in an amazing collection of musicals including Hamilton, The Color Purple, Les Misérables, To Kill A Mockingbird, Scottsboro Boys, and more. Today we cover a myriad of topics including Broadway's current corona-induced blackout, generalized anxiety disorder, quarter life crises and their roots, the ways that timing can impact a romantic relationship's trajectory, and so much more (BDE anyone?). TW: we also get dark at some points discussing topics such as depression, suicide, and 9/11. However, overall, this is a delightful episode with many performative moments between the Broadway veteran and Caitlin. We finish up by playing a new game inspired by Kyle's annoyance with New Yorkers who don't wear masks entitled "10 Things I hate About You: Corona Edition."Follow Kyle on Instagram @sirblackalot and see his shows on Broadway and more. 

Allie and Lexi Kaplan are my friends, Gemzeez creators, artists, reality and TikTok stars. Their episode is hilarious with the twins discussing everything from their business ventures (Gemzeez, TikTok, art, Inst@famous, Ex on the Beach, etc.), to twinspeak, dating as twins, our adventures in LA together, and so much more. We also cover deeper topics such as the twins' substantial fall-out, how dating younger men can be the move, how to grow from past relationships, covid changing the way we cherish our relationships, and more! Do not miss out on this episode it's one of the best. Follow Lexi and Allie on Instagram and TikTok @the_kaplan_twins or their individual and business accounts @alliekaplan, @lexikaplan, and @gemzeez. Learn more at their website http://www.thekaplantwins.com/ and buy Gemzeez on https://gemzeez.com/.

Lukas Thimm is a host, writer, actor, politico, and Housewives savant. Lukas starred as the only male host of Verizon Media's Build Brunch series, where he interviewed many amazing people including some legendary Real Housewives stars. While on the show, Lukas came to terms with his sexuality and was able to transform into the most authentic, honest version of himself (hence the episode title). Lukas gets raw and opens up about how he struggled to come out after years of suppressing his sexuality. This episode contains incredibly light, fun moments as well, as we cover everything from Housewives that Lukas has met, the guests who were not so impressive, and which Cuomo brother he’d rather sing drunk karaoke with. Caitlin meanwhile mispronounces every name possible. Don’t miss out on this episode, especially all you Housewives fans! Follow Lukas on any platform @lukasthimm, watch his web series “Best Friends Give the Worst Advice."

Kate is a comedian, writer, "stay-at-home daughter," and co-host of "Stage 4 Clinger" podcast with her mother. I found Kate after her impressive interview on "Girls Gotta Eat" podcast, where I was taken aback by her ability to be both so very dark and so very funny. On today's episode, we start by giving a background on Kate and eventually delve into loss, dealing with a parent with mental health/addiction issues, and toxic romantic relationships. Caitlin gets deeper and more vulnerable about her own experience than in past episodes and describes the ways in which her own story relates to Kate's experience. At the end of the episode, we play "7 Tea Questions" where Kate discusses everything from working with the Kardashians on "Kocktails with Khloé," to which celebrity would embody her wonderful therapy dog Jolene. Caitlin also almost cancels herself with several borderline inappropriate jokes. Kate has done a ton of work to find the comedy surrounding her difficult circumstances and is truly a light in a sometimes dark world. Do not miss out on this amazing episode and find Kate on Instagram @katenichollzz and her podcast @stage4clingers. Listen to Stage 4 Clingers wherever you get your podcasts. 

Caitlin has the honor of sitting down with Grammy Award winning artist André Anjos, AKA RAC in the episode "Let(ting) Go ft. RAC." In this episode they cover quite a bit, including but not limited to how André created RAC as a college internship, his experience cold calling The Shins' manager at the beginning of his career, performing in front of massive crowds as an introvert, navigating friendships at the height of success, his new album "Boy," and so much more. As André says himself, this interview delves deeper into more personal sides of his story than many he has done in the past, while still showcasing his light and upbeat personality throughout.Follow André @RAC on Instagram, Twitter, Spotify, and and all other platforms and listen to his new album "Boy"

Sally Olivia Kim is the CEO and founder of anti-aging collagen drink company Crushed Tonic and the author of The Collagen Glow. Sally was quickly climbing the ranks doing digital strategy at Condé Nast when she suffered a severe burn to her arm during a cooking accident. After trying seemingly everything, she found that ingesting collagen was the key to regenerating her skin. What started as something she did to help herself developed into a lifestyle routine that she needed to share with her family, friends, and eventually the world at large with the Crushed Tonic formula. In this episode, Sally tells her story and delves deeper into her personal psyche as well, discussing topics as serious as the sexism she has faced as a female CEO and as light as her love of smoking weed before bed. In between, we cover unrealistic beauty and body standards, disordered eating, the struggle to maintain friendships with a busy work life, the meaning behind the company’s catchphrase of “don’t want to grow up," and so much more. Follow Sally on Instagram at @sallsters and Crushed Tonic @crushedtonic. 

In Abel's episode "You Can Like Beyoncé and Still Be Racist" we mix things up; rather than the usual interview-style conversation, centering on the guest's career, the quarter life, etc., Caitlin brings on her incredible friend Abel to have a frank conversation about race and the current events triggered by George Floyd's death. After getting into everything from the week's political change to how our Instagram feeds have transformed, Abel opens up his recent "cocktail of emotions" and fear triggered by the harsh realities of our country and its racist tendencies. He goes on to discuss a reflection piece he shared on Instagram recently about growing up in a predominantly white neighborhood and getting harassed by peers for being both black and gay (the latter which he had yet to come to terms with). Finally, Abel highlights "badass queen" of a mom and how lucky he feels to have her and his family's unwavering support as a gay man, especially in light of their more conservative Ethiopian upbringing. Follow Abel on Instagram @abel.tessema to learn more.