How to get to know decent people?

[sahxox]

I start a lot of threads, but oh well lol
I can become very apathetic towards others, or I can get extremely anxious and chicken out of conversation efforts.
My effort rate is about 50/50, which is awesome cos it used to be 0.
Basically I'll give you a scenario.
One of the people at work (I've been here for two months) seems really nice and we always greet each other like old mates.
But we never talk really... it's almost like it's too late to randomly be like "so, do you have another job?" etc. so if I say something, it's relating to how long her shift is or whatever. But I'd feel stupid repeating the same question every time I work with her lol
I dunno what to say or how you could befriend someone in this situation. We've worked together too long to try and break the ice like this. Maybe I should just be like "how's your day been?" or something. Try and steal some info for next time haha
I'd have to execute such a statement with confidence, which takes effort. I said before that I only make an effort if I 100% know I won't be rejected, so it can't be said half-heartedly or it may be weird. Gahh so simple but so complex.
Similar situation with a few others who I'd actually bother with. Any icebreaking tips or casual ways to get to know them would be great

 

[Capsaicin]

Does anything worth talking about ever happen on the job? You could use it as a starting point and gradually move to related topics.

 

[laure15]

This is a problem for me too. When I first meet strangers I have plenty to talk about. I ask plenty of questions like "where do you live?" "what major are you doing?" "how's your job?", etc. But after I get to know this person better, I run out of things to ask or talk about. I find myself repeating the same questions or topics over again. It's boring for both of us. So we usually go watch a movie or do some activity that doesn't require a lot of talking. It gets old pretty quickly.

 

[ForeverTheWeirdKid]

Don't worry about looking stupid. If you're truly talking to a decent person they still may judge you..understand that it's just a defense mechanism...that is easy to break with persistence.

 

[SamD]

Try to make the conversation all about THEM. If there's one thing most people (besides SA sufferers!) love, it's talking about themselves. So when you're thinking of stuff to say, make it about them/their life if you can.

 

[¯\(º_o)/¯]

I have worked at my job over 5 years, it hasnt been until about the last year or so that I have started really talking to my co workers. Some ive started talking to as recently as a month ago after all these years.

I usually start with asking what they do out side of work for hobbies or for fun, and ask them about their families and usually just snow balls from there.
Its never been an issue with anybody that I didn't talk to them for so long and have just started

 

[Odo]

Notice something about them. Like something they're wearing or something they're reading. It could even be something like the way they carry themselves. If you say the wrong thing or they just don't like you it could come off as creepy, but mostly people like to talk about themselves.

General questions are pretty boring... try to focus on something specific about them, or something that you definitely have in common.