Three Chicago comedians—Eunji Kim, Jeff Brumfield, and Kenya Elan—offer their expert advice on navigating the inevitable awkward holiday conversations. The holidays, after all, are a time for family, food, and those cringe-worthy moments you’d rather avoid entirely.
Jeff Brumfield suggests starting with light small talk. “Small talk gets a bad rap, but it’s necessary,” he says. “You can’t just open with ‘Did you have sex today?’ Start light: ‘How’s it going? Did you see this wild thing on Twitter?’ Ease in. It’s like stretching before a run.” Kenya Elan prefers a more direct, albeit potentially rude, approach: “‘Why are you here?’ It can come off as rude, but hey, it gets people talking. Or, ‘Is this your first drink?’ Depending on how they answer, you know how to proceed.” Eunji Kim advocates for expressing opinions rather than facts, suggesting, “These people seem fun—or not.’ It forces them to share their own take.” She also champions “route talk,” sharing, “Did you take Ashland to get here?’ I turned 35, and now I live for shortcut conversations.” However, Elan cautions against asking about someone’s route to the party, deeming it a “vibe killer.”
The comedians also offer advice on handling potentially explosive topics. Brumfield advises avoiding sensitive subjects like family drama: “If you know someone’s getting divorced or there’s some deep tension brewing, just don’t touch it. You’ve got a whole buffet of topics to choose from and you’re reaching for the radioactive casserole?” Kim notes that the appropriateness of conversation topics can depend heavily on the group dynamics, citing the P. Diddy trial as an example of a subject that didn’t land well with a particular crowd. Elan adds, “Who you voted for, when you’re having a baby, and how many glasses of wine you’ve had. Let’s just agree no one wants to discuss these things—except that one guy who always has a lot to say and nobody wants to hear it.” Conversely, Kim advocates for open discussion of mental health: “Personal problems. Let’s normalize talking about it at the dinner table. Why wouldn’t you want to know if someone you love is struggling?” Elan jokingly suggests total transparency about finances and even admitted misdeeds, quipping, “How much money you’re making. Let’s just all put it out there. We can rise up together! Also, if you stole something to make the meal or wrap the gift. We’re all cutting corners these days. Own it.”
Finally, the comedians share their escape strategies for particularly awkward situations. Brumfield suggests the classic “empty cup” tactic: “An empty cup is your best friend. ‘Oh, I just need a refill’ or ‘Bathroom break!’ Works every time.” He also admits to simply turning and walking away without explanation. Kim opts for direct honesty: “Lately, I’ve started being honest: ‘I don’t want to talk anymore.’ I’m over 40, so I feel like I’ve earned that.” Elan employs a more social, albeit slightly manipulative, approach: “I find someone else awkwardly standing around, pull them into the conversation, get them talking and then I ghost. It’s a little messed up, but hey, I’m building community, even if it’s under duress.”
They also shared their approaches to handling unwanted gifts. Brumfield would lie, Kim would win an Oscar with her performance, and Elan would wear the gift once before donating it.
The article concludes with brief biographies of each comedian and credits for the story.