How can I be more playful with a man?

Finding common ground is a great way to build rapport and create a fun atmosphere for joking around. If you both have a shared interest or hobby, use that as a starting point for your humor. You could make a joke about a funny experience you had while doing that activity or use it as a reference point for a playful comment. When joking around with a guy, it's important to keep things light and avoid humor that could be perceived as mean or hurtful. Stick to playful teasing or self-deprecating humor that doesn't take itself too seriously.