So I sometimes talk about keeping a "mildly subversive" vibe, when chatting up women. Like you (or you both) know something that others do not, or to use humor in a bold way.

Here is an example of what I mean: In the past couple of weeks I went on an impromptu date with a young woman who, as it turns out, owns her own business. She kept asking me - in subtle and inoffensive ways - about my finances, but eventually, I called her out on it and she explained that men she dates find out that she's well off and suddenly they expect her to pay for everything, etc. Now, she's young, and not experienced enough to see past her own solipsism yet, but I saw an opening:

Me: "Oh, don't worry....I only want you for sex!"

Verdict: Killshot.

She erupted in giggles. I spoke to her a few days later. Her: "I told my friends about you! That I met a man who only wants me for sex!"

This accomplished a few things. First, I disarmed her biggest fear - never mind that she hasn't figured out that, as an older, successful man, I have no need for her $$$ - Second, I established myself in a sexual frame. That it made it far easier for her to give in, when the time came. Third, it also established me as a clever, witty guy.

Takeaway:

Quick on your feet is quick to the sheets.