12 “Dinner Party Questions” That Are Controversial — In a Good Way

As I approach my third holiday season with my husband, I pretty much know the drill by now. For Thanksgiving and Christmas, we’ll shuffle back and forth along Illinois’ barren winter highways between the south Chicago suburbs and my hometown near Wisconsin. Then, we’ll hastily depart a great-aunt’s home before lunch is served, scramble to arrive at a cousin’s feast for dessert, and return to my parents’ place where we crash after a long day of socializing.

The whirlwind days filled with nostalgia, tradition, and togetherness can leave me in a bit of a tailspin. The conversations can blend together. The Gen Z and Gen Alpha cousins’ new slang makes me feel like a decrepit crone. I confuse the names of my husband’s new-to-me third cousins. A matriarch asks me, once again, when I’m giving her grandchildren (*pops the cap off a $5 Trader Joe’s Sauvignon Blanc*). 

My husband and I love our families, and as sort-of newlyweds we’re still getting to know one another’s relatives better. That’s why it’s so important that for every family gathering we visit, no matter how fleeting, we make the connections count. And that’s where a dinner party question comes in.

And to find some excellent options, I’ve turned to TikTok. Every so often, a bizarre scenario or absurd “would you rather” goes viral. One of the best ways to stay focused and engaged during the holiday dash is to come prepared with a handful of these bonkers conversation starters. Whether you’re stuck in Thanksgiving traffic with the love of your life, or cornered in the dining room by someone you think might be Uncle Bernie (or is that Cousin Adam?) you need something to chat about. Here are 12 totally creative, definitely strange dinner party prompts to help you learn more about the guests at your gathering.    

TikToker Sabrina Flores (@withlovesabrinaflores) asks, “If your loved one owed the mob $50,000 by the end of the month, what would you guess they’d do to get that much money in that time frame?” Look, I’m not going to get into what I’d do, but, yeah, it likely involves my feet. 

I’ve never thought about my own hands as liquid dispensers, but here we are. Thanks to creator Hunter Ka’imi, I now know my own answer to the question, “Which five liquids would I want to be able to dispense from my own fingertips at any given time?” (Gasoline, water, iced coffee, Fabuloso all-purpose cleaner, and Cholula, baby!) 

The responses to the viral Tiktok conundrum, “Where would you hide a paperclip in 20 minutes if the FBI were en route to find it?” expand the full breadth and depth of paperclip possibilities. I fear authority and would likely be waiting in my front yard with my hands up, paperclip exposed. 

As a player of Dungeons and Dragons, I appreciate the fantastical potential that an animal companion offers. Tiktoker @thegraymattersblog asks which animal you would choose to animate from a handheld figure, along with several interesting caveats. 

The same Tiktoker poses the question of the tradeoffs of sacrificing a year of one’s life in exchange for one million (non-taxable, non-traceable) dollars. Considering $1 million barely covers a grocery store trip these days, I think I’ll keep the year of my life. 

This prompt from @questionsforlove is for those who can handle a little constructive criticism. Ask your loved ones what warning they would give a person you were heading out with on a first date. I just asked my husband this about me and he said, “She might get a migraine.” He’s not wrong! 

This question is one of my favorites. Nicole Rose (@its.nicolerose) asks, “What two totally normal things that if you do them back to back becomes really weird?” For me, it’s binge-watching a true crime docuseries and then heading to the hardware store to buy a shovel. (I haven’t done this, I promise!)

I often think about how my beloved pet corgi is kind of like half worm, half fox (and 100 percent perfect). Ashleigh Carter (@ashweecarter) asks, “If you could breed two species of animal together, which ones would they be and explain your work.” The “explain your work” part kills me. 

I’m a very nosy shopping check-outer and love catching a glimpse at the array of items in nearby carts. Why does this person need so much glue? What recipe are they making with these ingredients? From which aisle did they get that shirt and do I have time to grab one? Jared Seay (@jseay_) levels up the check-out game with the following question: “What is something you would buy at the store to make a cashier incredibly uncomfortable?”

Thinking again (and always) of my chaotic corgi, Rodeo, I often wonder which celebrity I’d want to voice my pet in a movie. I only have one choice for my pup: Jenny Slate. 

I hope I never find myself in this situation, but if I do, I have a plan! Parlay House asks, “If you had to dance for 30 seconds to save your life, what song would you dance to?” Play Fat Joe and Ashanti’s “Wut’s Luv” on my deathbed and I’ll bounce back. 

My Grandpa Jerry was a particularly candid and outrageous gentleman, so this question made me chuckle. Ashleigh Carter asks, “What is the craziest thing your grandparents ever told you?” Unfortunately for our readers, my answer to this question is too unseemly to print.