how to have a conversation that also has dirty jokes?

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1. This is something you shouldn’t start out your social-skills-improvement journey with, in my opinion. If you don’t know what you’re doing, then as soon as you drop one of your clever dirty jokes, the converstion is over and when the girl tells her friends, you were the creep.

   Here’s how people tend to do it, in any case (as an example): Instead of straight up telling canned jokes, they intentionally misinterpret whatever was just said to mean the sexual meaning of it. Picking that up and clarifying whether you heard correctly already achieves the desired results, which is making the person think of it and finding it amusing or funny. In some cases, your conversational partner drops double entendres all over the place (quite often unintentionally) and all you would need to do is make a face as a reaction to what they just said and they will get it immediately. Ideally, they visibly enjoy this playful element. If not, it’s time to stop.

   There’s a lot of examples on Youtube, come to think of it. Search for “Craig Ferguson adult talk” or “Craig Ferguson flirting” and you’ll see a master doing this. The channel “Charisma on demand” also has some good content on this.