In this episode, Madi and Katie dive into a messy AITA-style dilemma: is accepting free drinks at the bar harmless fun or a major relationship red flag?

They react to a wild Reddit “Am I The Asshole?” story about a woman who takes $600 from a customer to have coffee behind her boyfriend’s back, then connect it to real-life dating situations:

-Getting free drinks at the bar while “talking” to someone
-How much honesty you owe a new partner vs a serious relationship
-Whether withholding details is basically lying
-Dating boundaries, trust, and early exclusivity expectations

If you’re into AITA stories, dating podcasts, girls’ night drama, and real talk about modern relationships, this episode is for you.

Presented by Charm Diamond Centres

Summer Special is ON, and we’re diving into some seriously messy “Am I The Asshole?” Reddit drama. 🌶️

In this episode of Ring on It, Madison and Katie react to a story where a woman is freaking out because her friend keeps calling her boyfriend… “boyfriend.” Is it just a harmless vocal tic, or a walking red flag? 🚩

We get into:

Friend who calls everyone “boyfriend” and “girlfriend”
Whether it’s jealousy, boundaries, or valid intuition
Katie’s own habit of saying “girl” and “girlfriend” to literally everyone
Why ignoring someone’s clearly stated boundary is a BIG problem
When “seek professional help” crosses the line 😬

💍 Brought to you by Charm Diamond Centres

📲 Follow us on Instagram:
@ringonitpod – for clips, behind-the-scenes, and more stories

👍 If you love relationship hot takes, don’t forget to like, comment, and subscribe for more Summer Special episodes!

In this episode, Madi and Katie react to a Reddit AITA story where a roommate sleeps naked on top of the covers to teach his flatmate’s girlfriend a lesson about… knocking. We get into:

🚪 Privacy vs. pettiness – is he an asshole or just fed up?
👀 The girlfriend who keeps barging in uninvited
🙈 Our own “walked in on” horror stories (parents, boyfriends, random friends… it’s all here)
💬 Whether intention actually matters when things get messy
We debate who’s really in the wrong, how far is too far when proving a point, and why some people REFUSE to knock.

Brought to you by Charm Diamond Centres

🔔 Subscribe for more Summer Hotline / AITA episodes
👍 Like this video if you love messy Reddit stories
💬 Comment below: Is he the asshole for sleeping naked on top of the covers?
📲 Follow us on Instagram and TikTok: @ringonitpod

Summer Hotline is officially open for the season, and we’re kicking things off with a fiery “Am I The Asshole?” drama straight from Reddit. In this episode, Madi and Katie dive into a story about a drama school couple, a very flirty co-star, and a “stage kiss” that might have gone way too far.

Madi and Katie break down the situation from every angle: jealousy vs. intuition, trusting your partner vs. calling out boundary-crossers, and why some people seem to only want someone once they’re taken. Katie also shares a wild personal story about dealing with girls who deliberately go after guys in relationships, including some seriously malicious behaviour that caused major issues in her own love life.

If you’ve ever side‑eyed your partner’s “work wife,” co-star, or that one “friend” who doesn’t stay in their lane, this episode is for you. We talk trust, red flags, emotional cheating vibes, and what a healthy reaction could look like when someone clearly oversteps.

Ring on It is presented by Charm Diamond Centres.

For more modern love, commitment chats, and messy relationship dilemmas, follow us on Instagram @ringonitpod and subscribe for more Summer Hotline episodes all season long.☀️💍

Season one: done. Period. In this episode, Madi and Katie sit down to spill everything they learned (and low-key cringe at) over 25 episodes of Ring on It, presented by Charm Diamond Centers. We’re recapping the chaos, the growth, and the glow-up.

We revisit some of our favourite moments: our very first (terrifying) recording with Carla, early episodes with janky lighting and handheld mics, and the guests who showed up and got real about anxiety, dating, and mental health. We deep dive back into the debate that broke our brains: what’s a bigger commitment, a marriage or a mortgage? With expert insight from mortgage pro Clinton Wilkins, we talk “death loans,” breakups, refinancing, and why houses and relationships have more in common than you’d think.

We also celebrate big wins with one of our most wholesome stories ever: paying off massive student loans and marking the moment with an “RIP student loan” cake. We talk about “accomplishment cakes,” why small wins matter, and how celebrating yourself can feel just as big as a ring or a house key.

If you’ve ever wondered how a cute little wedding podcast turned into a chaotic, unfiltered look at modern relationships, mortgages, and red flags, this episode is your all-access Season 1 wrap.

Presented by Charm Diamond Centres

Hit subscribe, follow us on Instagram @ringonitpod, and get ready—season two is about to be even more unhinged (in the best way)!!

In this episode of Ring on It, Madi and Katie sit down with Halifax book influencer Courtney Sharp, aka @thesharpreader, for a chaotic, cozy, and very honest chat about reading, romance, and real-life relationship “icks.”

Courtney also opens up about her real-life romance story: a long-distance relationship, the private proposal at Shubie Park, and her aquamarine Cinderella-inspired engagement ring from Charm Diamond Centres. From matching tattoos with partners to whether you should ever be friends with an ex, nothing is off-limits.

If you love romance books, hate them, or you’re just here for the hot takes on modern love, this episode is for you.

Brought to you by Charm Diamond Centres.

Follow us on Instagram: @ringonitpod
Guest: Courtney Sharp – @thesharpreader

Shelby joins the Ring on It girls to share how a UK truck driver, a global pandemic, and a dating app turned into a real-life love story. From socially distanced car dates in a gas station parking lot to navigating negative COVID tests just to see each other, Shelby walks us through how her Tinder match Jordan became her husband.

We dive into what it was really like to date during lockdown, the anxieties and “he seems too good to be true” moments, and how she built trust with someone who had just moved to Canada. Shelby also shares her journey as a social media manager and TikTok creator, from hiding behind filters to going live, building community, and dealing with people calling her “cringe.”

If you’ve ever questioned your love life, felt stuck in a situationship, or wondered whether it’s still possible to find something real on apps, this episode will make you feel seen, make you laugh, and maybe give you a little more hope.

Subscribe, rate, and comment to support the show, and follow us on Instagram and TikTok @ringonitpod.

From Halifax, Nova Scotia, to styling hair for Paris Fashion Week, celebrity hairstylist Deena Alawaid joins Madi and Katie to share how she turned a small-town beginning into a global career and why she ultimately chose to move back home. She opens up about going from hating styling to working with icons like Bella Hadid and Adriana Lima, and how leaning into social media led to a six-year ambassadorship with Dyson.

The episode also dives into relationships, support systems and boundaries. Deena shares how she and her husband balance her demanding career with marriage and kids, why having a strong village matters, and what real support from a partner actually looks like.

If you’ve ever felt “too small-town” for your big dreams, this conversation will make you want to send that DM, pitch that idea, and finally shoot your shot!

🔔 Subscribe for more conversations about modern love, commitment, careers, and everything in between.
📲 Follow us on Instagram: @ringonitpod

🎧 Brought to you by Charm Diamond Centres.