I have several scenarios and I'm getting stuck on all of them. Maybe you can offer some help:

Girl works in the same office space as me. We're not in the same company, (she actually works for a service provider we use often). I'm always cocky/funny and obvious DHVs around her. It's tough to fully flirt as we're both working, but one night several weeks ago she sort of hinted she wanted to go out after work one night and I said let's grab a drink. We did, it went well but not sexual at all. The night ended with a hug. I'm pretty confident she knows it was a 'date' and not just two colleagues grabbing a drink, but you never know. Since then it has been semi flirty at work but nothing obvious. When I hinted we should go out again she seemed to be distant.

the other scenario is networking events. They are at a bar, so the environment is flirt. But everyone is there with name tags and wanting to hawk their business. I flirted with, and exchanged cards with an HB a few weeks ago. She wanted to talk about building a website, I told her we should grab pizza. We emailed and connected on FB, but when I pitched the meet she went cold.

How do you guys handle hitting on a HB who works with/for/against you? How do you break through and game the girl without making things awkward forever or looking like a creep?