Sorry for the rant.

Sorry in advance, this is just a workplace rant. I'm honestly getting really fed up with the way my boss interacts with me. Half the time I feel like he talks to me like I have a "little lady brain." It's not the 1950's guy.  I was hired as an administrative assistant not your personal errand chic. When I was hired I told him I was eager to learn new things, and that I prefer to be busy and I was led to believe that there are tons of work projects that I would be doing but that's most certainly not the case. I haven't learned a thing since starting this job and I'm starting to think it was a bad career move.

Normally I just brush his demeanor off but yesterday he just really irked me. He wants me to check the lotto from JULY to see if he has any winners, he wants me to go out of my way to legal sea foods to get him a $100 gift card (which he expects to be done on my own time), book vacations for him and his children, pay his personal bills, confirm a reservation for his EX wife, and then asks me to stay late because he'd like to get some bills paid (something actually work related.) This is commonplace and  I'm pretty flexible and often times I will stay late but yesterday I responded with "Sorry I really can't stay late tonight" and he very strangely replied "What are you crying?" to which i was very taken aback and then he proceed to come into my office half jokingly offering me a tissue. It was a strange encounter and I had no idea what to say. It was off putting to say the least and I honestly feel somewhat disrespected that I can't say no to staying late with out a rude retort.

I shouldn't have to stay late if he would prioritize work tasks over his personal errands but he regularly interrupts my job to have me do something completely unnecessary. He'll have me get off the phone with vendors, or our software company to do something he could do, that isn't part of my job. It's to the point where I'm starting to get uncomfortable. It makes me uncomfortable to take care of his personal accounts, especially since he doesn't pay half of them. It makes me uncomfortable to hear about how his ex-wife doesn't handle her finances well, his overdue bills show that he doesn't either.

Back to him making me feel stupid- I did check the lottery tickets he gave me (from 7 months ago) and informed him that "sorry you didn't infact win 20 grand but you did win a dollar" to which he replied "check it again, do it tomorrow though". Like I wasn't smart enough to be able read a winning lottery ticket. I'm sorry but alcoholic, white trash, drug addicts can tell whether or not they've won they mega millions- I'm more than capable. He makes comments, and really weird jokes all the time. He thinks he's funny but most of the time it makes me feel super awkward and like he has no respect for anyone beneath him.

I'm still trying to figure out the "crying" comment since there was no tone in my voice that would even insinuate that i was upset, I simply stated that I could not.