Hell Gate’s 2025 Guide to Navigating Difficult Thanksgiving Conversations

Thanksgiving is a time to contemplate what we are grateful for in our lives, to prepare an elaborate dinner, and, for many of us, to enjoy the company of family. But as we all know, family members don't always see things the same way, and sometimes conversation around the Thanksgiving dinner table can get a little rocky. 

Navigating these difficult family encounters can be stressful, frustrating, or downright traumatic. It's important to remember that you can't control how your family behaves, but you can control how you respond. With that in mind, Hell Gate would like to offer some examples of how to productively engage with loved ones over the Thanksgiving holiday.

Scenario 1

Your uncle Danny, who owns a car dealership on Long Island, interrupts a story about your co-op shift to say that he'd never live in New York City, because the crime is out of control, the subways are murder traps, and "illegals" are taking over.

Solution: You could blow your top, call him a racist MAGA blowhard who doesn't know what he's talking about, storm away from the table, and poison the whole family gathering. Or, you could try saying something like this: 

"Well Danny, when I talk to everyday New Yorkers—no matter where they're from originally—they all share many of the same concerns. They all want safety, and they all want justice. But what they want most of all is a city that they can afford to live in. I bet affordability is even an issue for you guys in Syosset, right?"

Boom! You can bet Danny has some gripes about the cost of living he's ready to share—now you're back on the same page and the conversation is back on track. 

Scenario 2

Every Thanksgiving, you make cheddar mashed potatoes as a side dish. And every year, they're a hit. But this year, your father-in-law is insisting that you make the gross sweet potato pecan casserole instead—the one with marshmallows in it. No one actually wants to eat this, especially because the turkey he prepares is dry and flavorless, but Frank is adamant: "My house, my side dishes." 

You could stand on your principles and stick with the cheddar potatoes, but that might involve an uncomfortable scene. Everyone is looking to you to save a Thanksgiving tradition.

Solution: Make the disgusting marshmallow abomination. After all, your father-in-law has done a decent job raising such a wonderful family, and this is arguably a small price to pay to stay in his good graces.

To smooth it over with the rest of the family, tell them, "We need not choose between justice and safety, and with this decision, we are affirming our commitment to both. And while Frank and I don't agree on everything, we both share the same passion for furthering an agenda of a successful Thanksgiving, one that delivers on a promise of fellowship, football, and a pumpkin pie at the end." 

If one of your cousins points out that this sweet potato side dish is basically a dessert, and one that is far too similar to pumpkin pie, sidestep his question with something like, "No, what I believe, is that both cheddar potatoes and sweet potato casseroles should be taken seriously, but that at this juncture, the imperative to execute on the casserole should take precedence so that our larger goals, those that involve a restful and meaningful holiday, ultimately prevail."