Okay, I got this hb9 coming to me really shy, but she told everyone she is interested in me. I work at a party store and she is a costumer. It got bad to the point to the part where my boss my dad is pressuring into asking her out. I have no idea how to approach this so I pretend to play hard to get. She doesn't approach me directly so it's obvious I have to approach her. I hate approaching people I see on a regular basis, I do better with strangers. This about the third time a situation like this arose I blew the first two by probably returning the interest. Sooner or later she will lose interest in time I need to transition to from playing hard to get to returning interest without her knowing or seeming different.

I hate to be a dick, but you just have to pull the trigger. Next time she comes in just say "I've been wanting to go to this sushi restaurant (whatever) but none of my guys will go with me, I think you should keep me company." Then after you get her number tell her you'll "Call her when you are hungry." Just come off like its not a big deal.

I guess you have to work on your inner game and just know that this is a time sensitive situation and you have to act and know you are the shit. I understand were you are coming from with the whole easier to talk to strangers, but you have to overcome this stuff and game her like any other girl. Just casually suggest going out wherever and see if she bites. She probably will and then tell her you'll call her, get her number and proceed from their. Just switch off that part inside you that says "this can wait" or "its not worth it". Those are usually the two phrases that run through my head when I'm making excuses. Ignore them and pull the trigger.