I feel like the only person who read the OP and actually understood what Halo was askin-

Oh. Hank did too... I think.

If I make a flirtatious joke or comment, unless it's with someone I'm romantically involved with or interested in, I do it expecting the other person to understand it's a joke and bat one back. If the other person does not understand that it's oft a joke then, understandably, the relationship can become a little strained or awkward. This is because it shows that we do not share a similar sense of humour, and I've always thought that was important when building up close relationships, platonic or otherwise. While it's definitely not going to stop me from trying to become friends with someone, responding well to the not-quite-flirting definitely makes the relationship build up far smoother.