I find small talk to be annoying if it goes on for more than a minute or two. If a conversation stays topical much longer than that, I'll generally end it. If someone I hardly know starts telling me all their personal drama, I actively avoid them from then on.

I live on an island in the middle of the St. Lawrence River on the border between the US and Canada, this is my 4th island and I can tell you that islanders love to know your business, they have no problem peppering you with questions about you and your past. My wife finds this terribly rude and intrusive but I find it fun, I am happy to answer their questions to a point and then after that if I feel they are getting too nosy then I just make shit up. I figure why not, mess with them since they are messing with me by prying too much. Usually the truth is sufficient to throw them for a loop but you should feel free to let loose with some really strange shit if you think your neighbours are too intrusive.

I dislike chit-chat unless it's with someone I truly like or I'm interested in in some way. I'm not good at just being polite for long so I'll give it a few minutes but, after that, I end it. I have no idea why he would want to share his life story with a stranger just because they happen to live in the same neighborhood.

Maybe I'm being harsh but it just seems awkward and desperate to me.

Any man who tells you such intimate things is letting you know that he's in the market for a new sex partner, and when you listen and laugh, it could be seen as flirtation by both the man and anyone watching.

I don't let married men tell me private things or talk to me for very long at all. I have boundaries and either firmly change the subject or tell them I'm busy and don't want to talk now. I can put an edge on my voice that makes them move along.