Personally I'd say it depends on the guy and the level of interest. But in my case I tend to stick with it until I get some definitive response from a woman that I'm interested in indicating she's not interested in me. To answer one of your questions, talking about a job/income can just be self-ego stroking as much as it can be construed as "flirting". To answer another, if you want someone to open up or engage you in conversation, try asking them about things they want to talk about, rather than meaningless questions (example, asking someone to elaborate on a hobby/interest).

I agree with Fireath-it depends on how interested he is. Im very shy too, and Ive had guys who just turned and walked away as soon as I didnt respond, and Ive had guys be very very persistant. I dont know how to tell you to muster up the courage...you just have to do it! Its not like you have to go up to him and ask him to father your children. just ask him one day at work if hed like to go out for drinks after work sometime. Or drop by his desk on your lunch break and ask him if he wants to come eat lunch with you. I know how scary it can be, but youll never know unless you put it out there and try it!

I believe that if life gives you lemons, you should make lemonade. And try to find somebody whose life has given them vodka, and have a party.-Ron White

OK, I just reread your comment and Im not really sure why I had the impression that you two worked together...but you still get my point, right?

I believe that if life gives you lemons, you should make lemonade. And try to find somebody whose life has given them vodka, and have a party.-Ron White

I'll second the "go out there and try it". Don't get me wrong, trying is the first step toward failure, but if you don't make an attempt, you'll never succeed either. Take it from someone who used to be shy and now gets up and eats a nice big healthy bowl of Rejection Flakes (tm) for breakfast every morning; there are far worse things in life than getting turned down. In fact, facing that fear is a great way to overcome it and become a more confident person. Just don't expect it to be easy.

The director of my department sends out "daily doses" with clever little quotes, alot of time having to do with courage...here are some he has sent to us in the past.

Why does the thrill of soaring have
to begin with the fear of falling? -- Mother Eagle

Many of life’s failures are men who did not realize
how close they were to success when they gave up.
-- Thomas Edison\

Courage is fear holding on a minute longer.
-- George S. Patton

Courage doesn't always roar. Sometimes courage is the little voice at the end of the day that says I'll try again tomorrow. ~Mary Anne Radmacher

Courage is doing what you're afraid to do. There can be no courage unless you're scared. ~Edward Vernon Rickenbacker

I believe that if life gives you lemons, you should make lemonade. And try to find somebody whose life has given them vodka, and have a party.-Ron White

Go for it. Strike up a simple conversation (So, how about that local sports team?). Ask him to go for coffee or something of that nature. I used to be really shy too, and didn't know how to react when a guy showed interest, but with the help of friends and forcing myself to get out and be a little more outgoing, I'm managing to get over it.

assuming you see this guy fairly regularly, just strike up a casual conversation. tell him about something funny that happened to you yesterday. even if you get a chuckle or smile out of him that's progress, you don't need to have him dying of laughter. then make a lot of eye contact, smile and if you feel even more daring, touch his arm a bit.

as for any new guys you may encounter, i suggest the eye contact, smiling and touching bit if you are still too shy to respond to compliments.