Long term user, name changed for this.
So, a while ago, my company got a new CEO. Nice chap, family man etc.
Sometimes works out of our office as more local to his home then HQ.
First time I met him I was dressed very casually, with my hair in 2 long plaits, some jokes were made. But office is very casual so no one cared.
Overtime he started to use me (I am the office manager) as a sort of PA, I'm good at what I do, and he valued my input and I figured, what the hell, possible career climb.
Comments kept getting made about my pigtails and how pretty I am. But I could never find anything inherently wrong and asked a guy friend who said he didn't feel it was inappropriate but more banter.
Cut to now. I've been furloughed for a few months. Office is starting to return.
Cue a text from said CEO, to my personal phone, saying "hi ---, hows furlough been? Missed your pretty face around the office the last few months..."
Second message slides in
"I have some policy I could use your input on, but only if you wear your hair in those pigtails...."
It's made me really uncomfortable. Really uncomfortable.
This feels like a step too far. It was one thing when jokes were made, and silly comments in company emails but this is my private phone.
I'm not overreacting am I?
I haven't replied yet.