Hey. So... It sounds like you are rather reserved with respect to meeting new people. When you go out with a friend then you expect that to be a time for you and your friend to connect and you feel uncomfortable when he shows in interest in getting to know other people who are around when you are out together.

I am like that by nature, too. But that being said, I've become open to different ways of being with respect to having a number of friends now who have a different attitude with respect to meeting new people. I have a number of friends now who like to go to the pub with me then while they are in the pub they have eye contact with other people and they are open to including them in our conversation. My ex boyfriend was more like this than most, however, with respect to happily chatting to waitresses and bartenders etc as well. It did come as a bit of a shock to me at first... Especially when we were on a date somewhere... But I decided to give it a go and kind of followed along from his lead and... Found that it was quite enjoyable, actually. We had time to talk, but we got to know other people as well.

It might be that he is demonstrating poor judgement in being so open with strangers... Or it might be that his judgement is a little different from yours in the sense of his being more open to making friends. It might be that he hasn't been as burned by strangers as you have and so he is basically more trusting of others (rightly or wrongly). I think a little about people spitting in my food so I do try and be pleasant and respectful of serving staff... But exchanging pleasantries can help make life more enjoyable (put you at ease a little). I'm not sure...

I do understand your not being happy with his disclosing something that you shared with him, however. It might be that he doesn't understand your being so sensitive / closed about it, however. How do you think the waitress responded to his disclosure about you? Was she basically sympathetic? Judgemental? Maybe you felt too embarrassed (thinking she must be bored to death with him or be thinking he must be desperate for friends for him to be chatting with her) to notice???

I don't know... Different ways of being perhaps...

It might be that he didn't mean to embarrass / humiliate you, though. If you tell him that that is how you felt then he might be able to be more discrete with your disclosures...