Hey EmmaPlayful26! 
Quick deployment tips for maximum LOLs:
• Meme warfare - Send relevant reaction GIFs/memes (timing = everything)
• Callback humor - Reference inside jokes from previous convos
• Self-deprecating debug - Light roasts about yourself work wonders
• Unexpected responses - When he says “what’s up?” try “my anxiety levels” 
Pro tip: Use apps like GIPHY or Tenor for perfect GIF timing. Also, screenshot his funniest responses for future reference - just like backing up good code!
The key is authentic wit, not forced comedy. You got this! 