You might want to see a therapist or attend support meetings for those with ADHD. You can learn more social cues from this. - I've never ever understood that people don't come from a place of friendship no matter how you are interacting with them. I'm unable to treat someone as their "position" rather than a human being who might just be kind. (Once they've proven they are unkind I get it). But a bit of therapy about how other people interact with the world would have been great. - It also might help the inferiority complex.

Remain at work and in work mode while on the premises, then take everything about work off your mind until the next work day. Buying your boss breakfast unasked could be considered inappropriate at best...worrying about how she treated your breakfast gift IS innaproprpriate. A co-worker could report you for "trying to buy favors". Please stop this behavior and just do your job during the hours you are paid to work!

Stop trying so hard! And don't take everything so personal. Some people just don't like people spending money on them. Relax take a deep breath do you job to the best of your ability and stop there. Above and beyond isn't required. Take your co-workers advice and give her space, some bosses don't like to get to friendly with their employees.

My assistant manager messaged back and said I overwhelm people. I have no social skills whatsoever. I didn't have friends growing up. I never get to hang out with my close friends. I just need to learn boundaries. I grew up a loner. I was ahead academically in school, but I had no one but teachers to talk to.

She is a bully and a toxic person. Stay out of her way and find another job as soon as possible...or go above her and report her to her superior. I am sure there are others in your job that will do as well. You are not the first person she messes with. No, nope.

The important points have been covered.

I would add only this: if you know you are a sensitive person AND you know someone has a history of messing with people to the point of making them cry, you need to avoid that person, as much as possible.

That is a bully and sensitive people are like catnip for bullies. (I should know.)

Do your job, do it well and stay out of her way. She has an employee who will come in early to bring her food, not only that but comes in on her day off to try and sort out a personal problem. Most bosses would love an employee like that. If she cannot appreciate you then look for a better job or better boss. What you tried to do was a kind thing. Now she may have thought that you were trying to curry favor with her. If so just keep your distance. Same goes if she is playing mind games. Just keep doing your job well and maybe look for another one.

So not in the work world but are folks normally on Messenger with their bosses? I find that odd. Also what if you send a private message to the wrong person?? Gees. Just curious not judging. Messenger didn't exist when I worked full time.

You boss sounds horrible. Like a horrible person. When you know someone is going to misinterpret what you say to the point of tears - you don't do it. Period. Everyone is somewhere different in understanding what lies under what is being said/expressed, If you have a Human Resources Department you may need to go to them. You do sound like you have issues - but this boss is making it all so much worse (deliberately?!). HR might be able to facilitate a sit down meeting. "Messing with people" is not good leadership behavior. If you aren't in therapy I'd suggest it so you can get stronger from what you've survived instead of still feeling like a victim. - So I'd first suggest speaking to your boss - perhaps including the 2nd person she "messes" with. And from there Human Resources if it isn't resolved or doesn't improve.

Do you have social contact with these people you work with after work. If so that complicates things. If this is just something happening while at work, I suggest you be professional, do your work as required and not get into petty work related issues with other employees including bosses. (IMHO)

You strike me as an extremely sensitive person. I get you were trying to be nice. It was a lovely gesture. However, it wasn't well-received. Regardless of what people are telling you, I'd err on the side of caution. No more gifts of any kind for anyone at work. Stop trying to figure out other people's motivations and just concentrate on doing your job. If your work environment is as toxic as you've described, it might be time to start looking for something else, somewhere else. Don't up and quit, but definitely start looking for a new job. Don't trust anyone you work with. If you're always feeling bad about yourself and second-guessing everything you do, perhaps professional counseling is in order. I think most of us could benefit from a little therapy on occasion. Don't let the assholes get you down.

What kind of work do you do and in what sort of organization?

In general, it seems like you have a lot of anxiety and might benefit from seeing a therapist. Also, most of the time what happens at work is not personal.

Check out, "The Four Agreements": It is a book that many, including myself, find useful. Good luck!

1. Be Impeccable with your Word: Speak with integrity. Say only what you mean. Avoid using the Word to speak against yourself or to gossip about others. Use the power of your Word in the direction of truth and love.

2. Don’t Take Anything Personally
   Nothing others do is because of you. What others say and do is a projection of their own reality, their own dream. When you are immune to the opinions and actions of others, you won’t be the victim of needless suffering.

3. Don’t Make Assumptions
   Find the courage to ask questions and to express what you really want. Communicate with others as clearly as you can to avoid misunderstandings, sadness and drama. With just this one agreement, you can completely transform your life.

4. Always Do Your Best
   Your best is going to change from moment to moment; it will be different when you are healthy as opposed to sick. Under any circumstance, simply do your best, and you will avoid self-judgment, self-abuse, and regret.