58-Year-Old Meets His 22-Year-Old Filipina Fiancée (First Time, 5 Days Ago)

#AgeGapLoveStory #FilipinaFiancée #ExpatDream

58-Year-Old Dean meets his 22-Year-Old Filipina fiancée for the first time — just 5 days ago at the General Santos airport — and the story will blow you away.

Dean (58, divorced from America) and Angel (22, a recent college graduate in Elementary Education from South Cotabato, Philippines) built their relationship on Filipino Cupid after a year-long LDR filled with false starts, video calls, and late-night chats across continents. When Dean finally stepped off the plane in General Santos, the first hug wasn’t even from Angel — her father sprinted ahead and embraced him with open arms. That moment, captured on video, set the tone for a love story that has already defied doubts and stereotypes.

In this exclusive interview on Fly Me to the Philippines, Chrissy and I (Rob, co-author of the Amazon #1 bestseller Fly Me to the Philippines: A Modern Man’s Guide to Living, Traveling, and Finding Love in the Philippines) sit down with Dean and Angel just five days after their first in-person meeting. Together we unpack the raw truth: what it means to fall in love across

Manila nightlife, Cebu City adventure, Dumaguete expat life, CDO (Cagayan de Oro) mountain escapes, Boracay island hopping, Bohol Panglao beaches, Siargao Island surfing, Davao City retirement, South Cotabato family traditions, Cebu Pacific Airlines flights, and even a dream of a 25-day travel island-hopping honeymoon vacation across the Philippines. If you’ve ever imagined living, dating, or traveling in the Philippines — this story connects directly with your own hopes and doubts.

💍 Highlights from Dean & Angel’s Story:

How Angel, a no boyfriend since birth (NBSB) woman, slowly built trust with an older foreigner she first thought was out of reach.

Why Dean at first told her she was “too young” and even suggested she help him meet someone older. That honesty became the foundation of their friendship… which soon grew into love.

How Angel handled tampo (a classic Filipino relationship moment) when Dean blocked her during a fight — and how they found their way back to each other.

Their first romantic nights together in a luxury suite at Ultra Winds in Cagayan de Oro, perched 1,000 feet above the city with views of the Cagayan River and the Philippine Sea.

Dean’s vision of buying mountain property with horses and building a future together in the Philippines, while also planning for a K1 visa journey to America.

This isn’t just another age-gap romance video — it’s a blueprint for men in their 50s, 60s, and 70s wondering if they can still find meaningful love in the Philippines. Whether your dream is Manila nightlife, a Dumaguete expat haven, Davao safety, or Boracay sunsets, you’ll hear firsthand how real couples navigate the trials, tribulations, and blessings of family acceptance, cultural differences, and genuine intimacy.

📚 CALL TO ACTIONS

👉 Get our bestselling book on Amazon: https://a.co/d/dd5dEz0

👉 Hire Chrissy for a $200 Open Source Social Media Investigation: https://flymetothephilippinesconsulta...

👉 Schedule a consultation (includes a FREE 10-minute meet & greet): https://flymetothephilippinesconsulta...

Whether you’re curious about retirement in CDO, dating in Dumaguete, island hopping through Cebu Pacific Airlines, or just want to know if a 22-year-old Filipina with no boyfriend since birth could genuinely fall in love with a 58-year-old American man — this interview has answers.

This video is a deep dive into the realities of cross-cultural love, long-distance romance, and the future of Western men seeking new beginnings in the Philippines. It’s not scripted. It’s not polished. It’s the real, raw story of Dean and Angel… and maybe the encouragement you need to start your own journey.



Stay tuned for Part 2 when Chrissy interviews Angel one on one