I'm on a first date with her. We're sitting on a couch next to each other. She brings up the dreaded work topic. After talking to her about it for a bit, I veer off into more interesting territory.

"Are you good at navigating bad situations at work?" I ask.

She responds that she is.

"What if you were sitting next to a guy at work, and he did this?" I move my hand onto her upper thigh. She looks at me and laughs.

"I would do this," she says and takes my hand and gently puts it back on the couch next to me.

This is a win-win gamble. If she leaves your hand there, it's awesome. You could even take it further. "Okay, but what if he did this?" And you escalate even more.

If she moves your hand away, you can compliment her and say, "I like the way you handled that. I would hire you to work for me."