Over A Glass Or Two

Tagay pa! Jessy Daing and JCAS are joined by their ultimate travel buddies, Vee, Joe, Monica, Ghia, Joan, and Anna, for a loud, tipsy, and wildly hilarious Taglish roundtable. When you put long-time friends in one room with flowing wine, expect absolute chaos, non-stop laughs, and pure truths about building a life abroad.

Real vs. Fake: Cutting out toxic people and keeping friends who celebrate your wins.

The Mirror Effect: Stop romanticizing people who treat you like an option.

Love & Marriage: We debate whether love is a feeling, a choice, or a little bit of both.

Secure the Bag: The unfiltered immigrant truth about why making money first is the secret to finally funding your passions.

Grab your glass and join the chaos!

Email your anonymous questions to: [email protected]

Watch the video version on YouTube: @OverAGlassOrTwo

The wine is still flowing, and the chikahan is getting deeper! Jessy Daing and JCAS return for Part 2 of our incredible, unfiltered sit-down with OPM icon Rachel Alejandro and her Spanish husband, Carlos Santa Maria. (Fun fact: Carlos reveals this is only the second interview he has ever agreed to do in his life!)

From debating Gen Z's respect for legends like Madonna to sharing deeply personal stories about surviving toxic relationships, we are laying it all on the table.

Grab your glass and join the conversation!

In this episode, we dive into:

👗 Madonna, Gen Z & "Acting Your Age": We discuss the internet's reaction to older pop icons, the pressure to dress a certain way as you get older, and why true confidence has no age limit.

📈 Leveling Up & Toxic Friends: Should you job hop for a higher salary? We talk about career growth and the harsh reality of "friends" who disappear or secretly hate when you start succeeding.

🚫 The "Path Not Taken": Does the road not traveled actually matter? Carlos shares powerful, life-changing advice from his father on why looking backward is toxic and why "what ifs" simply do not exist.

🚩 Fighting for Love vs. Walking Away: How do you know when to be relentless in a relationship and when to pack your bags? We discuss finding your breaking point, and Carlos introduces us to the ultimate Spanish wake-up call: the "Sartenazo en la cabeza" (a hit to the head with a frying pan!).

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Episode 402 - S17 E8: Rachel Alejandro & Carlos Santa Maria: 16 Years of Opposites Attracting & Moving to Spain (Part 1) 🥂

Jessy Daing and JCAS are popping open the wine for a very special, two-part sit-down interview! Tonight, we are joined by the "Queen of Heartbreak Songs" herself, OPM icon and international actress Rachel Alejandro, alongside her Spanish husband, Carlos Santa Maria. From hilarious travel habits to the realities of a 16-year multicultural relationship where opposites truly attract, this is Rachel and Carlos like you’ve never heard them before!

Grab your glass and join the chikahan!

In this episode, we dive into:

🧲 Do Opposites Actually Attract?: Carlos had zero girlfriends before Rachel. Now, they’ve been together for 16 years despite radically disagreeing on almost everything. We dissect why having different hobbies works, as long as your core values match.

🇪🇸 The Big Move to Spain: Carlos talks about returning to Valencia, his birthplace, while Rachel opens up about the realities of balancing her international acting and singing career. We discuss how she plans to navigate her busy travel schedule and keep their bond strong as they build a new life in Europe.

👨‍👩‍👧 Family Ties & Daily Calls: We compare our family dynamics! Rachel shares why she still calls her parents every single day, while Jessy and Carlos open up about their different approaches to keeping in touch.

📸 Travel Vibes & Photoshoot Patience: Jessy defends her "40-minute OOTD photoshoot" travel style, while Carlos and JCAS explain why they prefer a quick snap and a trip to the nearest pub.

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YouTube: https://www.youtube.com/@OverAGlassOrTwo

Facebook: https://www.facebook.com/OAGOT.US

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Episode 401 - S17 E7: 50/50 Finances, Fake Friends, & Reinventing You: Is Marrying for Money Wrong? 🥂

Jessy Daing and JCAS are back and holding nothing back in this brand-new episode of Over a Glass or Two! From navigating the tricky waters of splitting the bill with your partner to dealing with two-faced friends, we’re unpacking the modern realities that every Global Filipino faces. Grab your favorite drink and join the conversation!

In this episode, we dive into:

💸 The 50/50 Relationship Rule: Should couples split everything down the middle, or is the "traditional" way still alive? JCAS jokes about the "sugar baby" life, while Jessy breaks down why keeping score can ruin a relationship.

📱 Social Media Envy vs. Inspiration: How to protect your peace online. We talk about the pressure to flex, people faking "lobster dinners," and why you should treat your feed like a personal photo album instead of a competition.

✨ Reinventing Yourself (Version 2.0): You don't have to start from scratch to level up! JCAS shares her exciting new journey into fashion design and sewing, while Jessy discusses the upcoming launch of her skincare line. Plus, we celebrate OPM icon Tootsie Guevara’s inspiring comeback. It is never too late to chase a new dream.

🐍 Confronting the "Gossips": What do you do when a close friend stabs you in the back? We share our raw, personal experiences with "friends" who invent lies and why someone who gossips to you will definitely gossip about you.

💍 Marrying for Financial Stability: Is it automatically a red flag to want a wealthy partner? We debate the unfair "gold digger" double standards and why financial comfort is great—but only if there's real love, respect, and balance to back it up.

🎧 CATCH UP ON PAST & NEW EPISODES:

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📺 WATCH US ON:

YouTube: https://www.youtube.com/@OverAGlassOrTwo

Facebook: https://www.facebook.com/OAGOT.US

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Want to share your story or ask for advice?

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Episode 400 - S17 E6: Dating App Scams, "Red Flag" Jealousy, and the Truth About Success

Jessy Daing and JCAS are back with another raw, "no-filter" conversation over a glass or two. From the struggles of finding love in the digital age to the reality of toxic relationships and the "karera ng buhay" (race of life), we’re diving deep into the topics that every Global Filipino can relate to.

In this episode, we dive into:

📱 Dating Apps: Savior or Scam?: JCAS shares the "stages" of online dating - from matching to avoiding "AI Catfishing". Plus, we talk about "Raya," the exclusive app for celebrities and millionaires .

🚩 Jealousy vs. Proof of Care: Is a jealous partner a red flag or just someone who loves you? . Jessy opens up about her past experiences with extreme jealousy .

💔 Staying for the Kids: A heart-wrenching look at whether staying in a toxic environment "for the children" is actually the right choice.

🎓 The Academic Excellence Myth: Does a straight-A record guarantee success in the real world? We discuss why "Street Smarts" (Maabilidad) often beats "Book Smarts" when it comes to thriving in life and business.

🤫 Being Ignored vs. Being Lied To: Which one hurts more?. We break down how being ignored affects your worth, while being lied to destroys your trust.

🎧 CATCH UP ON PAST & NEW EPISODES:

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📺 WATCH US ON:

YouTube: https://www.youtube.com/@OverAGlassOrTwo

Facebook: https://www.facebook.com/OAGOT.US

📧 CONNECT WITH US:

Want to share your story or ask for advice?

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Episode 399 - S17 E5: Celebrity Throwbacks, "Convenience Friends," and the Real Circle of Life

Jessy Daing and JCAS are reflecting on the journey that brought us here, from the high-glitz world of TFC to the raw, honest conversations we’re having today.

In this episode, we dive into:

🚩 The "Convenience Friend" Reality: We have a candid talk about why the friends you expect to support you are sometimes the quietest, while total strangers become your biggest cheerleaders.

🔄 The Circle of Life: How to handle the shift from being "the big thing" to starting over, and why your value isn't defined by who claps for you.

✨ Choosing Happiness: Amidst the challenges of 2026 and the "fake" energy of social media, how do we find genuine joy?

🎧 CATCH UP ON PAST & NEW EPISODES:

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YouTube: https://www.youtube.com/@OverAGlassOrTwo

Facebook: https://www.facebook.com/OAGOT.US

📧 CONNECT WITH US:

Want to share your story or ask for advice?

Email us at: [email protected] (100% anonymous!)

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Episode 398 - S17 E4: Filipino Identity Abroad: Family Land Wars, AI Virtual Assistants & More!

🥂 Buhay na buhay at kicking again for 2026! Matapos ang aming "hibernation," Jessy Daing and JCAS are back to give you the real background of Over A Glass Or Two - mula sa aming TFC roots hanggang sa aming pagbabalik ngayon.

Hindi kami mag-ho-hold back sa mga topics na relate ang bawat Global Pinoy:

🏠 Inheritance at Land Wars: Ano nga ba ang nangyayari sa "Ancestral Home" kapag hindi nagkasundo ang magkakapatid? Greediness nga ba o katarungan?

🇵🇭 Heritage at Wika: Failing nga ba tayo as parents kung hindi marunong mag-Tagalog ang mga anak natin?

🤖 AI vs. Call Centers: Maapektuhan ba ang BPO industry sa Pilipinas? Share namin ang aming "robotic" encounter sa customer service.

Chapters:

00:00 Welcome Back to the OAGOT 2026 Season!

05:12 Inheriting Land: When Family and Money Collide

12:45 Will AI Wipe Out Pinoy Call Centers?

22:30 The "Tagalog" Debate: Parenting Abroad

48:20 Why Foreigners Can’t Bash Our Culture (But We Can!)

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Facebook & YouTube

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Episode 397 - S17 E3: Soulmates, Relationship Boundaries, and the AI Revolution for Global Pinoys

Grab your favorite mug (or wine glass!) because Jessy Daing and JCAS are back for another "no-holds-barred" session! We’re diving into the deep end-from the magic of finding "the one" to the high-tech hurdles of 2026.

In this episode, we strip away the inhibitions and get real about the modern Filipino experience. Whether you're in Manhattan, the Philippines, or anywhere in between, this conversation is for you!

In this episode, we dive into:

❤️ Soulmates vs. Timing: Is there really one person for everyone, or is it all about being in the right place at the right time? Jessy and JCAS discuss if a soulmate can be a friend, a sibling, or even "the one that got away.".

🇵🇭 The Tagalog Debate: Do you need to speak the language to be "truly" Pinoy?. We talk about the Gen Z and Alpha Filipinos abroad who are embracing the culture more than ever, even if their Tagalog is a little "baluktot.".

📱 The Password Pact: Should couples share their phone passwords?. Jessy shares how transparency transformed her 11-year relationship, while we debate the fine line between trust and intuition..

💨 The Ultimate Comfort Test: Is farting in front of your partner a "green flag" or a "brown flag"?. We talk about accepting flaws-from aging to triple chins-and why physical facades eventually fade..

🤖 The AI Onslaught: It’s 2026, and AI is everywhere-from summarizing doctor’s visits to delivering food in Jersey City.. We discuss the "scary" side of technology and why we’re worried the younger generation might stop thinking for themselves..

Whether you're "bed-wrapping" or listening on your commute, join our community as we navigate the humps and hurdles of life together..

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Episode 396 - S17 E2: Our Honest Thoughts on the Philippines Today & Why We Love The Global Pinoy Spirit

We are officially back for the 2026 season! 🥂 After our short break, Jessy Daing and JCAS return to the mic to catch up on life, travels, and what it truly means to be a Filipino in today's world.

In this episode, we’re moving past the surface and talking about the heart of the Filipino experience - the highs of coming home and the bittersweet realities we face.

In this episode, we dive into:

🏠 The Reality of Homecoming: Jessy shares her recent trip to the Philippines. While the new airports are impressive, the "real" Philippines - the traffic on EDSA and the poverty in Quezon City - left her with mixed emotions and a heavy heart.

🎄 Why Paskong Pinoy is Unbeatable: There is nothing like the holiday season in the Philippines. We discuss the "agile" and resourceful spirit of Filipinos who always find a way to celebrate bongga, no matter the struggle.

🍢 The Cravings are Real: From the best puto bumbong and bibingka to the street food we can't find anywhere else (Fishballs, anyone?), we talk about the flavors that define our childhood.

🌏 Global Pinoy Pride: Reflections on why so many Filipinos leave to work abroad and the resilience required to support families from across the ocean.

🏝️ Holiday Highlights: From family time in Chicago to a 14th wedding anniversary trip to the Bahamas, we catch up on the personal milestones that kept us busy during the hiatus.

Whether you’re a "well-traveled person" or just missing home, grab a glass and join the conversation as we look forward to a year of abundant blessings. 🍷💬

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Episode 395 - S17 E1

The Return of the Comeback | Over A Glass Or Two

Your favorite Pinoy talk show podcast is back - bigger, brighter, and bolder than ever! 🥂

After a long hiatus, Jessy Daing and JCAS return for a brand-new season of laughter, gratitude, and unforgettable stories that bring global Filipinos closer together - one glass at a time.

In this comeback episode, the hosts catch up on what’s changed, celebrate the people who’ve supported them, and look back on some of their most memorable guests. They talk about; Jessy’s TOFA Award as one of the 100 Most Influential Filipinos in the World, their good friend Rachel Alejandro’s inspiring movie Song of the Fireflies, meeting Ogie Diaz and watching his moving OFW film, flood control issues, and so much more - all in the signature OAGOT style that fans love.

It’s heartfelt, funny, and filled with Pinoy pride. Whether you’re tuning in from Manila, New York, Dubai, or wherever home feels like - pour yourself a drink, hit play, and join the conversation. 🍷💬

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