(and Why He Shouldn’t Look Back)
A San Diego expat landed back in California with a suitcase full of doubts. He’d just ended things with his Filipina girlfriend after months of feeling “something wasn’t right.” Now, alone in his apartment, the silence is deafening—and the second-guessing has begun.
I got his email last week. In this post (and the video embedded below), I’m sharing the exact advice I gave him—raw, no-filter, and rooted in years of watching expats repeat the same cycle.
What I Cover in the Video
- Why you should ALWAYS trust your gut feeling in relationships—it’s your subconscious flagging red flags your conscious mind wants to ignore.
- The danger of second-guessing yourself when you’re lonely—loneliness is a terrible relationship advisor.
- Why expats must be content alone BEFORE dating—if you can’t enjoy your own company, you’ll settle for anyone’s.
- How age-gap relationships often lack balance in intelligence and maturity—a 25-year-old and a 55-year-old rarely operate on the same emotional wavelength.
- Why dating should take second stage to personal contentment—build the life first; the right person fits into it, not the other way around.
- The importance of activities and non-romantic social connections—a full life leaves less room for bad decisions.
The Core Message: Your Gut Doesn’t Lie
He wrote: “I knew the whole time something was off, but I ignored it. Now I’m lonely and wondering if I made a mistake.”
No. The mistake would be going back just to escape the quiet.
Loneliness is temporary. A mismatched relationship is a slow bleed.
Actionable Takeaways for Expats
- Solo Test: Can you spend a full weekend alone abroad without spiraling? If not, fix that first.
- Gut Check Rule: If you feel “off” for more than two weeks straight, write down the reasons. Read them back in a month. 9 times out of 10, you’ll wonder why you waited so long.
- Age Gap Reality Check: Ask yourself: “Would I want my daughter dating someone my age at her life stage?” If the answer stings, there’s your answer.
If you’re dating in the Philippines—or anywhere abroad—subscribe for straightforward expat advice stripped back to basics. No fluff. No sponsored rose-tinted glasses. Just the truth from someone who’s seen the cycle too many times.
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