Hey everyone, what do you think I should do? The last two months at the office have made me super uncomfortable and I’m honestly so lost.

Okay, long story. I’m 26, office job in Chiang Mai, general coordination stuff — data entry, scheduling meetings, contacting vendors. Been here a year and a half. Normally I finish around five-something. Some days I stop for a quick meal from the street stall near the soi and eat at my desk, maybe read the news for ten minutes, that’s it.

The problem started when the new boss came in almost two months ago. He looks about our age, dresses more formally than the previous boss, speaks clearly and is pretty serious. But he has some behaviors that make me feel really weird. He’s been calling me to talk alone more often, without saying why. And the timing and tone are off — like one Friday at twenty past ten at night he DM’d me “are you free to talk?” I freaked out because normally bosses talk during work hours. I said I wasn’t available, and he sent a long message about work that wasn’t directly my job but it looped around with lines like “I want you to understand the team’s perspective more” said in this watching-you kind of tone that made my chest itch, I can’t explain it.

He also gives personal compliments a lot, like “Good job today,” then follows up with personal questions about what I ate or which shop I went to. I gave a short answer that I grabbed food from the soi near the office, and he sent a laughing sticker and a cat pic. Okay maybe just polite? But sometimes he brings up relationship status or asks what music I like. I don’t want to share that stuff but I feel forced to reply, so it gets awkward.

One time I came in extra early at seven to finish something for a client and he messaged “thanks for being on time.” I sent a photo of my polka-dot paper coffee cup from the shop next door and he said, “That coffee looks nice, take me there sometime.” Am I overthinking or is that weird? It really makes me uncomfortable.

There are times he’s a great boss — helps solve problems, explains things in detail. Once he stayed late helping me with a spreadsheet for like two hours and walked me through formulas until it was done, which I appreciated and felt like he cared about the work. But outside work hours his communication turns personal, so I don’t know how to interpret it. I’m so confused.

I’ve been trying to set my own boundaries, like replying shortly to messages outside work hours or waiting until daytime to respond. But he still asks about some work things after hours, so I’m unsure how to keep a rule without affecting work. If I say directly, “I’m not available outside work hours,” I worry I’ll seem cold or rude. I’m shy about saying it — afraid he’ll make a drama, or think I’m difficult. Not okay.

I’m most scared that if I speak up things will get worse, like he’ll think I’m uncooperative and that will affect future performance reviews. My feelings are all over the place, I’m sensitive, and I don’t want to tolerate this because my mental health is suffering. I can’t sleep well, waking up at 3AM thinking about it for 45 minutes T_T

Have any of you experienced this? If you were OP, would you talk to the boss directly or go to HR first? Has anyone tried politely but firmly setting boundaries and it worked? Tell me how. I’m scared to be blunt and make things worse. I want honest perspectives I can try — just hoping it won’t make the situation worse, haha.

P.S. Sorry if this is messy or the paragraphs are weird, I just finished work and I’m too lazy to edit.