5 Good Conversation Starters That Always Work in an Awkward Situation

Earn your black belt in small talk

Sure, you know your way around an uncomfortable silence or two, but when your kinda awkward coworker Rhonda corners you at the office happy hour (again), you’re at a loss. Here, five good conversation starters to use the next time things start to get weird.

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"wow, What An Interesting [insert Piece Of Clothing]. Where's It From?"

Think of this line as awkward conversation 101. The best way to get someone you’re chatting with to open up is to ask them about themselves. Clothing is the perfect entry point: If the person you’re speaking with is wearing something unique, bring it up. You’ll find it’s one of the easiest conversation starting points.

"are You Watching [insert Netflix Show Here]?"

At this point, Netflix--or HBO Go or Amazon Prime--is a universal talking point. (If someone doesn’t personally subscribe, they’re probably borrowing a login, right?) This means there’s a strong chance you’ll be able to find common ground by mentioning the latest hit show. For example, “OMG, did you catch season two of Unbreakable Kimmy Schmidt?” If the answer is yes, you can discuss. And if it’s no, you just bought yourself several non-awkward minutes selling them on why they should start. 

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"what Are You Up To This Weekend?"

Or depending on the timing: “What’d you do this past weekend?” This question is open-ended and it forces someone to volunteer a detail about their personal life, which you can then react to/ask probing questions in reaction to. (“Oh, you love to knit! How’d you get into that?” or “Oooh, you spent the weekend in Maine? What did you love most about the trip?”)

"what's Your Favorite Kind Of Cheese?"

OK, this sounds strange, but hear us out: It’s actually an amazing (and logical) conversation piece, especially if you’re in a setting where hors d’oeuvres are being served. As long as your conversation partner isn’t a vegan/lactose intolerant, there’s a lot to discuss. (“I love Gouda. Or burrata, but only with heirloom tomatoes, etc.”) Plus, who knows? Maybe the best cheese she ever ate was on a trip to Provence. Cue the conversation gold.

"to Be Continued"

OK, so she didn’t have epic tales of an adventure sampling cheese in Provence. Instead of faking the need to dash to the ladies' room, try: “You’ll have to excuse me for a sec. To be continued!” It’s positive and encouraging, but also vague, which means you’re off the hook if other (more stimulating) conversations prevent you from circling back. 

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Freelance Editor

From 2015-2020 Lindsay Champion held the role of Food and Wellness Director. She continues to write for PureWow as a Freelance Editor.