What makes Dave's normal speaking and storytelling so captivating is that he doesn't speak in monotone. He emphasises different words and adds different tones when he's speaking.

You can immediately improve your storytelling, especially if it's humorous, by speaking as if you're reading a book to a five-year-old. This will push you in the direction of more engaging storytelling, which is critical if you want anyone to laugh.

This is when you use your tone to create the expectation of one punchline, then throw a completely different one.

For example, leading with a serious and literal tone to an obviously silly and false punchline. Or, if you meet someone in a social environment and they ask you what you do for a living, you can make up a silly job like a professional boxball player, then riff on why it's so stressful in a serious tone.

Eventually, you will drop the joke and give a real answer so you can connect on a deeper level. However, it should introduce a more relaxed vibe.

Most people think that people connect over things like logistics. For example, they share where they grew up, what they do for work, or how they spend their free time. 

However, people connect over shared laughter. Allowing yourself to be silly with a tongue-in-cheek response can go a long way rather than perfect reasoning to convince someone.