3 of 5 I kept the new question, but most of your 'edit' section was really a reaction to comments.Try to work those it into the main body. Put the questions for experience in a smaller font. If you focus the post on everything at once it might well get closed for asking multiple questions at once.

How can I recognise that I am teasing someone too much without verbal feedback from that person?

In my situation, I am dating someone who is the typical class-clown type and enjoys being funny and making jokes. Sometimes our coworkers (we met at work) tease him and I'll join in. Most of the time it is all in good fun. But I noticed recently that it feels like I'm ragging on him all the time for things that aren't always good-natured teasing. He has expressed that sometimes I make fun of him when he isn't in the mood, or bring up unrelated things in the joke that makes it no longer funny.

There are a lot of resources online for how to respond to bullying and teasing. However, I don't see resources for people who would like to learn to stop teasing their friends and family.

We have already discussed it(it being the problem: me teasing him is not always nice) between us. He told me that he felt upset over a particular joke. I felt bad that I had hurt his feelings and asked him what I can do to not hurt his feelings again. He described other times when he wasn't in the mood for joking and I realized that while I could tell he wasn't 100% having fun, I didn't pick up that I was directly affecting him at the time. This was how I realized that I don't know how to prevent it going forward. I don't know how to tell when I am being hurtful because he admitted he is the type to bottle it up for awhile before telling me. He also told me that 90% of the time, joking and teasing doesn't bother him.

When I say I feel like I'm ragging on him all the time, I mean that half an hour after a conversation or exchange, I'll feel a little bad about the things I've said or brought up, but I'm not sure if it affected him and am belatedly realizing they might have been mean.

In reflecting on past experiences where I was notified after the fact, I observe the following:

  • The person being teased argued the premise of what they were being teased about (ie: "The reasons behind -- are --")

  • The person being teased seemed frustrated about the other activity the group was engaged in (hiking etc)

  • The person teasing was more engaged with other people doing the teasing than the person being teased

From these notes I gather that if the person being teased isn't laughing along and is redirecting the conversation in any way, that should be a Big Red Flag. Other indications of Big Red Flags would be very helpful to me.

How can I recognize that I am teasing someone without verbal feedback from that person?
In a conversation with 2 or more people where teasing is normal, what non-verbal cues can I look out for that the teasing in that moment is unwelcome?

If you have experience being teased where you were hurt or uncomfortable or know how someone felt during such an episode, I believe answers to the following questions could be beneficial in a well-rounded answer: What kinds of ways have you shown that you were uncomfortable? What things did you do to try to suppress your uncomfortable feelings that may have let the other party know you were uncomfortable (if they were unaware)?