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The Dating Orange

HeadStuff Podcasts

Dating can be tough, and I’m here to help you navigate it... or at least make you feel less alone while you're at it. What started as a faceless TikTok page sharing my own dating nightmares has turned into a podcast with me, my pals, and some well known faces. Whether you're single, taken, or somewhere in between, you are all very welcome, huns. 💘🔥

Bonus episodes are coming very soon to HeadStuff+ so watch this space. Become a member and support The Dating Orange at https://headstuffpodcasts.com/.

This is a HeadStuff podcast produced by Hilary Barry.

Artwork by Matt Mahon.

Got a story or want to chat? Contact me:

📧 thedatingorange@gmail.com

📸 Instagram & TikTok: @thedatingorange

✨️New episodes every second Tuesday!✨️

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22 episodes
weekly
Avg 28 min
English

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Tuesday · 41 min
TikTok Thirst Traps to Craigslist Catfishes with Ross
This week's guest is Ross (@unsub1989), content creator, activist, accidental political commentator, and self-described 'Paddystinian.' His online journey is a funny one. He started off posting tasteful thirst traps on TikTok and somehow ended up talking about housing, healthcare, and government policy. But today we are parking the politics, and we're getting into his dating life. Ross is bisexual, so he's seeing it from all angles. We talk about his disillusionment with hookup culture, how it's no easier dating men as a man, and some of the mad situations that he's found himself in over the years, including getting catfished on Craigslist and a date getting maximum financial value from him. Enjoy! Find ross on TikTok @unsub1989 To support the show and access ad-free listening and bi-weekly bonus content become a member at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠headstuffpodcasts.com/membership⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ This show is part of HeadStuff Podcasts. Produced by Hilary Barry. Artwork by Matt Mahon. Learn more about your ad choices. Visit megaphone.fm/adchoices
August 18 · 8 min
[Preview] Bonus: Matchmaking Adrian & Caroline
This week we hear from the wonderful Adrian & Caroline after their first date. To hear the full episode and access ad-free listening go to ⁠⁠⁠https://headstuffpodcasts.com/membership/⁠⁠⁠ to become a HeadStuff+ member. Learn more about your ad choices. Visit megaphone.fm/adchoices
August 11 · 44 min
Navigating Singles Events with Samantha Keating
Welcome back to The Dating Orange! 🍊 This week, the Orange chats with Samantha Keating, founder of Your Friend, My Friend, about running over 150 singles events across Ireland. Sam breaks down why meeting offline beats swiping on apps, why people need to give the spark time to grow, and the mystery of getting men to actually show up. This is a must listen for anyone done with dating apps. To support the show and access ad-free listening and bi-weekly bonus content become a member at ⁠⁠⁠⁠⁠⁠⁠⁠⁠headstuffpodcasts.com/membership⁠⁠⁠⁠⁠⁠⁠⁠⁠ This show is part of HeadStuff Podcasts. Produced by Hilary Barry. Artwork by Matt Mahon Learn more about your ad choices. Visit megaphone.fm/adchoices
July 28 · 46 min
From Courtrooms To Comedy with Justine Halpin
Welcome back to The Dating Orange! Today's guest, Justine Halpin, solicitor working in domestic violence by day and a stand up comedian by night, giving her a unique perspective on dating. Despite working tough cases daily, she’s held onto her sense of humor. She shares her own relationship experiences, including a Dublin actor who was seeing other women, leading to a surprising friendship and chats through bad relationships, red flags, coercive control and Jennie's Law. To support the show and access ad-free listening and bi-weekly bonus content become a member at ⁠⁠⁠⁠⁠⁠⁠headstuffpodcasts.com/membership⁠⁠⁠⁠⁠⁠⁠ This show is part of HeadStuff Podcasts. Produced by Hilary Barry. Artwork by Matt Mahon Learn more about your ad choices. Visit megaphone.fm/adchoices
July 21 · 11 min
[Preview] Bonus: Matchmaking Mairead & Conor
Tall? Check. Ginger? Snickers workwear? Check. The Orange may have found Mairead’s dream guy this week, but could he actually be the one? To hear the full episode and access ad-free listening go to ⁠⁠https://headstuffpodcasts.com/membership/⁠⁠ to become a HeadStuff+ member. Learn more about your ad choices. Visit megaphone.fm/adchoices
July 14 · 23 min
Nightmare Dates with Tracy from The Midlands
Welcome back to The Dating Orange! This week the Orange is joined by the wonderful Tracy from The Midlands. Tracy is a gas character who has lots of hilarious and shocking stories from years of trying to find a normal fella. If you've ever wondered where all the good and decent men have disappeared you'll enjoy this one. To support the show and access ad-free listening and bi-weekly bonus content become a member at ⁠⁠⁠⁠⁠⁠headstuffpodcasts.com/membership⁠⁠⁠⁠⁠⁠ This show is part of HeadStuff Podcasts. Produced by Hilary Barry. Artwork by Matt Mahon. Learn more about your ad choices. Visit megaphone.fm/adchoices
July 7 · 14 min
[Preview] Bonus: Matchmaking Triona & Richard
This week the orange is matching up Richard and Triona. Surely we don't have another case of ghosting on our hands this week!?.. 👻 To hear the full episode and access ad-free listening go to ⁠https://headstuffpodcasts.com/membership/⁠ to become a HeadStuff+ member. Learn more about your ad choices. Visit megaphone.fm/adchoices
June 30 · 17 min
Catfish: Who Is Behind Dr. Rudy Stein?
Welcome back to The Dating Orange! Three women got in touch with me separately over the space of a few months, all describing different experiences with the same man from a dating app… and it was only when they started comparing notes that they realised they hadn’t just dated the same person, they had all been speaking to the same fake identity. Tune in this week as we ask who is behind Dr. Rudy Stein. And yet, when it came time to meet him in real life, something always came up, something always went wrong… and eventually, after a bit of digging, the entire identity started to fall apart. To support the show and access ad-free listening and bi-weekly bonus content become a member at ⁠⁠⁠⁠headstuffpodcasts.com/membership⁠⁠⁠⁠ This show is part of HeadStuff Podcasts. Produced by Hilary Barry. Artwork by Matt Mahon. Learn more about your ad choices. Visit megaphone.fm/adchoices
June 16 · 28 min
Josie in Dublin: Normal People vs. Real Irish Lads
Welcome back to The Dating Orange! This week the orange is joined by Josie, a TikToker from Chicago living in Dublin. Josie opens up about moving to Ireland with Normal People expectations, only to be met with low effort pub dates and TikTok backlash for being 'too forward' for the men of Ireland. Keep up with Josie on TikTok @liketotallyjosie To support the show and access ad-free listening and bi-weekly bonus content become a member at ⁠⁠⁠headstuffpodcasts.com/membership⁠⁠⁠ This show is part of HeadStuff Podcasts. Produced by Hilary Barry. Artwork by Matt Mahon. Learn more about your ad choices. Visit megaphone.fm/adchoices
June 2 · 55 min
The Manosphere & Male Loneliness with Aoife Moore
Welcome back to The Dating Orange! This week the orange is joined by journalist and author Aoife Moore to chat about the recent Louis Theroux Manosphere documentary and the male loneliness epidemic. Plus, the Orange has an interesting story to get Aoife's thoughts on... Enjoy 🍊 To support the show and access ad-free listening and bi-weekly bonus content become a member at ⁠⁠headstuffpodcasts.com/membership⁠⁠ This show is part of HeadStuff Podcasts. Produced by Hilary Barry. Artwork by Matt Mahon. Learn more about your ad choices. Visit megaphone.fm/adchoices
May 26 · 8 min
[Preview] Bonus: Matchmaking Séan and Laura
Welcome to the very first exclusive matchmaking episode of The Dating Orange. This week, the Orange is matching up farmer Séan and teacher Lorna. They seem perfect on paper, but will sparks fly when they finally meet? To hear the full episode and access ad-free listening go to https://headstuffpodcasts.com/membership/ to become a HeadStuff+ member for just €5 a month +VAT. Learn more about your ad choices. Visit megaphone.fm/adchoices
May 19 · 37 min
JUSTINE…. I’M ENGAGED
Welcome back for a new season of The Dating Orange. This week The Orange opens up to good pal Justine Stafford about her recent engagement. This one is not to be missed! 🍊💍 To support the show and access ad-free listening become a member at ⁠headstuffpodcasts.com/membership⁠ and keep an eye out for bonus episodes coming very soon. Learn more about your ad choices. Visit megaphone.fm/adchoices
May 14 · 1 min
The Dating Orange Is Back
The Dating Orange is back and this new season dives headfirst into the chaos of modern dating, featuring real-life stories from everyday people, from a man with his own “baby reindeer” experience to a woman whose date faked his father’s death. Alongside comedians, journalists, therapists and content creators, the series explores everything from the manosphere and women’s safety to healing, heartbreak and the bizarre realities of finding love today. First episode is out next Tuesday the 19th and new episodes are released every second Tuesday on HeadStuff Podcasts or wherever you get your podcasts! To support the show and access ad-free listening become a member at headstuffpodcasts.com/membership and keep an eye out for bonus episodes coming very soon. Learn more about your ad choices. Visit megaphone.fm/adchoices
March 26 · 33 sec
Sign up for matchmaking!
Matchmaking is coming back for season 3 of The Dating Orange Podcast and it's bigger and better than ever, with HeadStuff Podcasts! Give it a go - you never know! Fill in the form here: http://headstuffpodcasts.com/orange
S2 · E25
Nov 7, 2025 · 30 min
Jennie's Law: Elma's Story
In this episode of my four-part Jennie’s Law series, Elma shares her story of leaving an abusive marriage after years of mental abuse. She talks about her ex-partner’s alcoholism, the safety order she obtained, his breach and conviction, and why she...
S2 · E24
Nov 7, 2025 · 47 min
Jennie's Law: Amanda's Story
Amanda shares her story of nearly nine years in an abusive relationship filled with violence, control, and addiction. Her ex had a history of violent convictions, struggled with gambling, drugs, and porn, and when he owed men money, they came to her...
S2 · E23
Nov 6, 2025 · 20 min
Jennie's Law: Sasha's Story
Sasha shares her story of surviving a brutal assault by her then-boyfriend, and fighting for justice. She talks about the challenges women face when speaking out, difficulties in the courtroom, and why a law like Jennie’s Law will make a real...
S2 · E22
Nov 4, 2025 · 41 min
Jennie's Law: Jennie's Story
This episode is all about Jennie’s Law, the proposed legislation aimed at protecting people from entering relationships with partners who have a history of domestic violence. Approved by cabinet and now before the Dáil, the law is a vital step toward...
S2 · E21
Oct 28, 2025 · 34 min
Catfish in the Cockpit
Dearbhaile matched with a man claiming to be an Aer Lingus pilot - he definitely was not a pilot but definitely was actually married with kids. For two weeks, he spoofed about his job, travels and life as a pilot, until Dearbhaile found out the truth...
S2 · E20
Oct 26, 2025 · 44 min
Filthy John: Monica's Story - Part 2
In the final episode of The Dating Orange Podcast, Monica talks about the challenges she faced after her relationship with John ended. She shares her disappointment with the lack of support from the guards and how she even faced a Tusla investigation...

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