11 long weekend conversation starters for deeper connection

Most of us have a complicated relationship with weekends.  Especially if it’s a long weekend.  Do you rest? Do you party? Do you — God forbid — work? Anyhoo… by understanding how someone spends their …

Most of us have a complicated relationship with weekends. 

Especially if it’s a long weekend. 

Do you rest? Do you party? Do you — God forbid — work?

Anyhoo… by understanding how someone spends their long weekend, you will understand how they value certain activities over others. It’s truly an underrated conversation topic.  

Here are a few questions I’d ask: 

Small talk

  1. Any plans this long weekend? // Doing anything this long weekend?  
  2. What would you like to do this long weekend?
  3. What’re you looking forward to this long weekend? 
  4. Catching up on sleep this long weekend? (lord knows how sleep-deprived modern humanity is…)

Deeper questions

  1. What would be an ideal long weekend for you? 
  2. Should a long weekend be productive or relaxing? 
  3. Is it ever OK to work on a long weekend – why or why not? 
  4. If you did absolutely nothing this long weekend, how would you feel?
  5. If you had no obligations/errands this long weekend, what would you do? 
  6. What have you been meaning to do on a long weekend but never got to? 
  7. What would be an absolutely irresponsible but fun way to spend your long weekend?  

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