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I do that if a person wants to have a conversation with me. But real problem comes when they don't initiate a conversation or when more people are involved.
When more people get involved I just shutdown, I only listen and barely add anything to the conversation.
When a person I know comes around me and doesn't initiate, I feel awkward I just don't say anything and ignore them which I feel is giving off a very rude image to them, but I can't help. "I'm not the extrovert between us why don't you initiate :(" is only thing I think of there.
Try to allow yourself to be genuinely curious about the other person, and to show them that, and ask questions about what you're curious about. Social interactions are about both the listener and the talker and if you can allow yourself to be vulnerable and share what you are actually feeling it really helps, but it also helps to be interested in them and what they are feeling and thinking. So trying to be curious is often a good go to.
I dunno i don't have all the context but I think you're too hard on yourself. That's a pretty typical interaction between two introverts standing around the kettle or something.
I would recommend scheduling a one-on-one lunch together. At lunch, think of yourself as a news reporter who needs to find all about this person. Where are they from? What was their family like? Why do they work here? What are their hobbies? See if you can get them talking about something that they have a strong opinion about.
See if you can do one of these every week.
I also think you would highly benefit from Toastmasters.
Toastmasters is the best piece of advice in this thread.