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Photo of Katie Grogg on a crossword puzzle background incorporating the TikTok logo Photo illustration: James Bareham/Polygon | Source image: THEGINGERB3ARDMEN

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One crossword-solver’s enthusiasm inspired an entire TikTok subculture

How Katie Grogg created the purest puzzling community

Crossword puzzles are so much fun ... until they’re not. For most casual crossword fans, there will eventually come a point while working on a puzzle where they get stuck on a clue (or two, or three, or four) that seems impossible to solve. But that’s not because the puzzler lacks the necessary knowledge or vocabulary to solve it; it’s simply because they don’t know all the rules. And one TikTok creator has made it her mission to make crosswords more accessible — and more fun.

Since February, Katie Grogg has been demystifying New York Times crosswords by sharing tips and tricks for solving them on her TikTok account, @coffeeandcrosswords. These run the gamut from going over basic rules (the tense of the clue and answer will always match) to the meanings of common clue terms and phrasings (a clue ending in a question mark indicates wordplay). She also unpacks more challenging crossword tactics, like giving detailed walkthroughs of how to solve themed puzzles, each of which has its own set of rules that deviate from the standard New York Times guidelines.

Grogg has always been a fan of crossword puzzles, but she didn’t start consistently doing them until six or so years ago. Now, “they’re just a part of my daily routine,” the 26-year-old told Polygon over Zoom. A professional singer who often works on cruises, Grogg found herself with far more free time on her hands than usual during the pandemic, a good portion of which she spent fostering her passion for crossword puzzles. (She got her first full month of perfect puzzles in December 2020.) That’s why when Grogg discovered a lack of instructional crossword content on TikTok, she decided, “Well, I’ll be the one to do it, then.”

When she began making TikToks, Grogg didn’t expect to get more than 5,000 followers. But in the months since @coffeeandcrosswords launched, her account has amassed more than 161,000 followers, and it continues to add thousands more each week. The CrosswordTok hashtag, which has more than 17 million views, has become nearly synonymous with Grogg’s account, though more and more creators are steadily adding their own crossword content to the mix. Grogg and CrosswordTok have even become such a recognized presence in the offline crossword community that she was featured as a clue in a USA Today crossword puzzle this fall. (Grogg has a copy of the puzzle framed in her room.)

The cornerstone of CrosswordTok’s appeal, at least in Grogg’s corner of the internet, is that it’s designed for everyone regardless of their knowledge or experience level. It’s difficult to find one of Grogg’s TikToks that doesn’t feature at least one user in the comments sharing how she’s inspired them to take up solving crosswords or helped them appreciate crosswords in a new way — and Grogg is often there, sharing words of encouragement right back. “I just wanted to thank Katie of @coffeeandcrosswords because look at this,” user @tamaroulette said in a TikTok, showing off a full month of completed New York Times crosswords on the screen behind her. “YOU ARE A STAR!!!” Grogg replied in duet, absolutely beaming with pride.

@coffeeandcrosswords

#duet with @tamaroulette you’re MY inspo god I’m obsessed w this community. #crosswordtok #crosswordpuzzles

♬ august - Taylor Swift

“Being able to break down clues and debunk the elusiveness or whatever of crosswords has been really exciting,” Grogg said, over Zoom. “So often when [...] I’m doing them around other people, they’ll be like, ‘Oh my gosh, I can’t do crosswords. I’m not smart enough.’ [...] And I’m just like, that is so not true. I couldn’t do them either when I started, and then you just learn the rules.”

Grogg also celebrates the challenges of problem-solving and the skill that goes into creating crosswords, building an infectious excitement in her community. “It’s honestly been a minute since a puzzle has made me smile this hard,” Grogg said in a TikTok about a compass-themed puzzle from April 2016, posted in response to a commenter’s question. As Grogg begins walking through the trick to solving the crossword in the video — the direction that each answer is written in is determined by its placement in relationship to the central compass square — it’s hard not to get caught up in her glee. “My heart just skipped a beat!” she exclaims at one point.

Live TikTok and Twitch streams, which Grogg started doing in the summer, have given her a chance to engage with viewers directly. In these streams. she does a New York Times crossword start to finish, and viewers in the chat suggest answers, theorize about the puzzle’s theme, explain the definitions of obscure answers, and just hype each other up. There are in-jokes, playful ribbing, and even a drinking game, where participants take a drink whenever there’s a French clue or a common answer, like “Oreo,” “era,” or “Alan Alda.” It’s impossible to ignore the camaraderie and warmth between Katie and the participants, many of whom she’s on a first-name basis with. And the more Grogg builds intimate connections within the CrosswordTok community, the more it grows: A record 6,000 people tuned into Grogg’s TikTok livestream on Oct. 28.

“It is the most wholesome, encouraging, positive corner of our little internet that I feel so lucky to be a part of,” Grogg said. “And [the Twitch viewers] are my friends. I really feel so close to those people, because we hang out three times a week.” Plus, Grogg added, “I love solving with other people because I don’t know a lot of answers.”

Of course, putting any content online will eventually draw some level of negative feedback. But so far for Grogg, those instances have been very limited. “I had one video where I messed up — like, I said something was plural instead of the right tense. And someone was like, ‘Girl, you’re crazy,’ or whatever. For a second, I was like, ‘Oh my God, they’ll never trust me again.’ And then it was fine. Like, it literally didn’t matter.”

The only time the smile ever slips from Grogg’s face during our Zoom call is when she’s discussing her upcoming hiatus from Twitch. In a few weeks, Grogg is setting out for the Caribbean on a Disney cruise where she’ll perform Frozen’s “Let It Go.” Though she plans to continue making TikToks, the poor Wi-Fi on the cruise means she’ll have to step away from Twitch until she’s back on land.

@coffeeandcrosswords

Answer to @dougiefingerpewpews no greater joy than a good question mark clue #crosswordtok #crosswordpuzzles #MMKx007 #SamsClubScanAndGo #fyp

♬ Spongebob - Dante9k

Grogg had been eager to get back to cruise work since the pandemic began nearly two years ago. But now that the CrosswordTok community has become such a large part of her life, returning to work has become a bittersweet experience, and she’s attempting to parse it out in real time. Reconciling her pre-pandemic life with this new life — and hopefully this new parallel career she’s carved out for herself within CrosswordTok — is something Grogg is only starting to figure out. There’s also the concern of burnout, something that’s become increasingly common with TikTok creators.

“I went in with some ground rules for myself,” Grogg said. “And one of those was, if this starts to make me not want to do my crosswords in the morning, I’m done. This is too much a part of my joy of life that it’s not worth it. And that has not been the case. It’s made me more excited.”

Regardless of how long Grogg continues to make crossword content, she’s comforted by the belief that CrosswordTok will live on. During a recent peek into the CrosswordTok Discord that her Twitch viewers created, Grogg learned they were putting together their own solving group during Grogg’s livestreaming hiatus.

“It’s so sweet. [...] And that’s what I want,” Grogg said. “That makes me feel like there really is a community.”