Make it clear that your supervisor is trapped in your conversation, not the other way around. When you have to be professional, be professional. But the rest of the time, talk about the dirt between the planks of wood at home. Talk about the sedimentation process of your aquarium’s gravel. Basically the moste innate and boring topics that no normal human would bring up, repeated ad nauseam.

Make sure to take long pauses just to resume talking. Remember to take your time while monopolizing the conversation trying to find a word your forgot about.

Remember to mispronounce every word, especially if he corrects you but be sure to keep plausible deniability just in case he accuses you of doing it on purpose.

Remember to always blame everything on something that has no connection to it.

Remember to enrich your diet with garlic, to use terrible flavored candy or just skipping a meal for extra word flavor, if you can take the reputation hit.

Remember the magical phrase: “that reminds me of” and all variants of it.

Remember to look into his eyes, and to alternate between them and another part of his face as if something is wrong with it. Keep affirming that everything is alright while staring at that part.

Change the subject. All the time.

Have terribly strong inconsequential opinions and remind about them all the time.

Monopolize the conversation, but make him want to cut you off or talk. I

IMPORTANT : If the other party is silent, state how comfortable you are with this silent friendship.

OP, I’d urge you to reconsider framing this whole thing as an “extrovert vs introvert” battle. Your boss is demonstrating poor boundaries and disrespectful and inappropriate behavior, and that has nothing to do with whether she’s an I or E on the Myers-Briggs.

Whether or not you go to HR depends a lot on your company culture. Either way, you need to be documenting specific comments and specific behaviors that are inappropriate first. Every time she asks you an uncomfortable question, especially if it relates to sex, write down what she asked, how you responded (that you declined to answer and asked her to stop asking personal questions), who else was present, and the date/time. Keep this in a personal account, not company. Do NOT go to HR without documentation.

We don’t know how big your company is, but odds are if she’s a middle manager she’s got people above her already who know she’s a gossip and hate that. If you have any relationship at all with her supervisor, it’s generally viewed as following the chain of command if you bring concerns like this directly to them, as well.

I’m an extrovert. That’s not the problem. This is social bullying. Please don’t frame this as “extrovert” behavior. This is reprehensible social interaction. As an extrovert I would NEVER talk about personal experiences at work. I would NEVER ask anyone to participate in my conversations unless they clearly wanted to. Stop conflating extroversion with bullying.

Can you just tell her that you like to have quiet time at lunch to recharge for the afternoon?

If you work at a company with a competent HR department they will be very interested in hearing about how your supervisor is forcing you to eat lunch with her while she interrogates you about your sex life. That is 100% not appropriate in HR world. Just don’t ever believe anyone in HR is actually your friend, stick to the truth always, and document everything. Literally, keep a log of everything. If you end up in lawyer world they will be very happy that you have documentation of dates and who was there and what happened.

It seems at least possible that her intentions are good, and you don’t want to blow up your job, right? Have you told her directly that you like her and like your job, but the lunch-and-interrogation is not your idea of a break, and you do need a break? With a smile, do not feel like you are doing anything wrong. You are not doing anything wrong.

I am surprised nobody else is sitting these out ever, if every other person in your group looks forward to the lunches and they are part of what she considers the culture of the department, maybe it’s important to her. But I have never worked anywhere where it was a requirement like that.

It honestly sounds like you’ve got deeper issues with your boss. I would just shop for another job.

I’m quite introverted and have learned to only respond to questions when asked. I have no issue sharing any information. However, I have a major issue with understanding the scope of information worth sharing and when to stop. I do not let myself feel awkward in silence or the need to carry any conversation. If a person piques my curiosity, I can talk with them for days. I can find something curious to talk about with almost anyone. People that lack depth become a repetitive conversation that I will avoid.

Personally, I don’t like to be actively manipulative with people. It goes against my nature. However, if someone annoyed me like this, and I had no other outlet. I would subtly use their psychology against them about like how a psychiatrist turns a conversation to introspection and analysis. Once a person is made vulnerable through unexpected introspection they are easily dominated. I can get away with a lot of things like this because I am a big dude where people expect me to be assertive and dominant in many ways that I really am not. Your results may vary.

As a fellow introvert, I’ve found that being meek and timid about uncomfortable situations just invites more trouble from extroverts. The best way to handle it is to be direct and firm. If she wants to be nosy, then drop all the gory details:

"I’m an introvert and I don’t feel comfortable sharing my personal life with coworkers. I know you, as an extrovert, want to be involved in everyone’s personal lives and there’s nothing wrong with that, but as a leader and a manager, you need to understand how to change tracks and adapt to your subordinates’ needs.

“I need time to myself to recharge; being around people is mentally and emotionally draining for me. It’s not something I can “fix,” it’s just the way I am, and no amount of exposure to people or social events will ever change that. I need you to understand that and adapt to my needs, in order for you to effectively manage me.”

I worked my way up the ranks in the US military and eventually found myself managing people. As an introvert, I found it extremely difficult to get out and talk to my subordinates. But I soon realized that the mission wouldn’t get done unless I did my job, so I quickly learned how to fake an extroverted personality while at work so I could talk to people and ensure mission success. Then I’d go home and crash. I’d spend my evenings either sleeping or bundled up, watching TV or playing video games, just to recharge so I could do it all again the next day.

But one of the things I learned was how to adapt to the needs of my subordinates. I had one guy who was a complete fuck-up. Couldn’t do anything right without someone holding his hand. So I either had to be very hands-on with him, or delegate that responsibility to one of my subordinate leaders.

But then I had another guy who grew up in a ghetto being plagued by corrupt cops, and he hated anyone in an authority position over him. Why he joined the military, I dunno. We were all about authority and respecting rank and file. But if I even spoke to him, he would shut down and then be unproductive all day. As long as I left him alone, he was my hardest and most productive worker. So I learned to leave him alone and he practically did my job for me. Maybe your supervisor needs to learn that lesson with you.