I tried Pattaya and Chiang Mai, but Bangkok wins for me. I like structure: gym near BTS, co-working in Thonglor, hospital 10 minutes away, and dates on tap. Yes, it’s pricier, but the value is real — world-class healthcare, international food, and a dating pool that never sleeps. If you’re mid-career or want momentum, Bangkok is the move.

After a year in Bangkok, I moved to Pattaya and my blood pressure dropped 20 points. Beach walks in the morning, massages in the afternoon, live music at night. My rent is half of what I paid in On Nut, and I have actual friends — guys I see daily for coffee. If you’re retiring or just want relaxed expat life in Thailand, Pattaya is easy mode.

Chiang Mai is for men who want routine and meaning. Cheaper condos, real community, and Thai culture that isn’t drowning in neon. I spend my days between cafés, Muay Thai, and weekend trips to the mountains. Dating is quieter but more genuine. The only headache is smoky season (Feb–Apr). Plan a beach escape or short stay in Bangkok those months and you’re golden.

Whichever city you choose, put healthcare and hospitals at the top. Bangkok has the best options (Bumrungrad, Samitivej), but Pattaya and Chiang Mai are solid too. If you have ongoing conditions, living near a major hospital beats living near the beach. Also look at visa runs, airport access, and how fast you can reach home if needed.

I rotate: winter in Chiang Mai for focus, spring in Bangkok for business and dating, and two months in Pattaya for beach recovery. Thailand lets you design seasons for your mood and budget. If you’re unsure, try all three for a month each. Your body will tell you where you belong — pace, sleep, spending, and how you feel waking up.