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The joy (and nerdery) of a crossword puzzle routine

There's nothing like the satisfaction of a completed crossword puzzle.

Webster’s forte (5 letters)

If you’ve talked to me in the past year, chances are good I’ve mentioned my thrice daily crossword puzzle routine. Yes, thrice. I orient my day around crossword puzzles and I’m proud of it. It adds structure to my day and gives me a regular dopamine boost of satisfaction. 

As soon as I’ve made Irish breakfast tea, I grab my laptop to check my email and two favorite Discord groups. Then for the real treat: the Washington Post crossword. (Technically their crosswords are syndicated from the LA Times. You have to watch a 15 second ad but they’re free.) Are there some mornings where my eyes have trouble focusing on the grid or my mind moves a bit slow? Sure. But I cannot tell you how much joy it gives me to start off my morning this way. No matter how the rest of the day unfolds, I completed something. 

Around lunchtime, I do the free crossword from Vox. After work, I do the Vulture puzzle—I have a New York Magazine subscription for this one. In fact, the Vulture crossword is where this obsession began. I subscribed a few years ago and loved working on the weekly crossword. Then I noticed they had a weekday one but they were almost too short and easy so I rarely did them. Until I thought to myself, “who cares if they’re easy??” 

My routine changes slightly on the weekend. Vox and Vulture have puzzles Monday through Sunday, while WaPo is weeklong with not one but three puzzles on Sunday: Daily, Sunday, and Classic. The Saturday and Sunday puzzles are my favorite because they’re longer and offer more of a challenge. But I love the “easier” weekday puzzles for the way they allow me to feel proud and accomplished. It’s the little things in life. 

Of course, there are days I oversleep, have lunch plans, or leave my laptop behind on vacation. It always feels strange to miss out on my routine. But it gives me something to look forward to when I get home. 

I’m not precious about how I finish a puzzle. I have no compunction about revealing a letter or word once I get stuck. My only goal is to complete it, however it happens. To that end, I ignore the timer completely.  If I come across a puzzle in a magazine or newspaper, I’ll fill it out in ink but I’ve come to prefer doing them on my laptop. (No apps on my phone. I don’t like the experience.) There are many people who are probably faster and more knowledgeable than me but this is one arena where I will not compare myself to anyone else—progress for this Enneagram Four. You might be wondering if I ever do the esteemed New York Times puzzle but that only happens if I’m visiting the Bogels. I’m not ready to add a fourth crossword to my day quite yet! 

An unexpected benefit of doing crosswords for so many years is the assortment of knowledge I’ve acquired. Random Latin phrases, the names of rivers and obscure animals, pop culture trivia, and the three-letter words puzzle creators adore (kimono sash, med. care provider, Spanish for gold). Then there’s figuring out what the theme means, be it a play on words or an homage to a holiday, sport, or movie. Not to mention cracking the rebus. It’s not just what you know or can call up from the recesses of your brain. There’s a rush in determining the answer based on context clues, reasoning, or wild guesses.

Over time, you get to know the personality of the creators. I love when a clue contains a cheeky aside that encourages you to exercise your civic duty or lets you know how they really feel about a movie or type of food. Recent example: a 3 letter word for “news website that produces the “Today, Explained” podcast (my check’s in the mail, right?).”

Whether the Chicago Tribune newspaper or my grandma’s People magazines, crossword puzzles have long played a role in my life. In college, I had a phase of working my way through crossword puzzle books, doing one after another after another. (Unsurprisingly, this is similar to my approach to working on jigsaw puzzles: once I start, I can’t stop.)

They were a part of my post-work de-stressing routine after a long day of conducting home visits as a hospice social worker. That routine continued through my move to Nashville but my newspaper habit lapsed after another out of state move. I didn’t realize how much I’d missed working on crosswords until my New York Magazine subscription. Now I can’t imagine how I went so many years without this routine. 

How do you feel about crossword puzzles? Please nerd out with me in the comments.

P.S. Check out our team’s whole Raving Fans series right here.

Leigh Kramer is the Editor and Social Media Manager here at MMD. Her go-to genres are romance, fantasy, and YA. You can follow Leigh on Goodreads.

47 comments

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  1. Ashley Cavell says:

    I love puzzles. I have a subscription the NYT Games and have a set routine of which games I do in which order. I can usually get them all done in the 10-15 minutes it takes to finish my morning cup of coffee. I’ll sometimes go for the NYT Crossword, but mostly stick to Wordle, Connections, Strands (that’s a new one!), the Mini Crossword, Vertex, and end with Spelling Bee. My grandmother instilled in me my love of puzzles as she truly believes it helps to keep her mind engaged as she ages and I also just love the challenge of all the games. You are also absolutely right in the way it’s taught me so many little pieces of random trivia and information.

  2. Nichole says:

    I LOVE a good crossword puzzle. I have worked the WSJ puzzle for years, but I still really miss the days when they only published one per week. It was gigantic and HARD, but it gave me such a sense of accomplishment when I finished it with only minimal help from looking up answers. This was obviously back when I had to do it on the actual newspaper. Thanks for the suggestions of a couple more to add.

    • Leigh Kramer - MMD Editor says:

      I don’t know if I’ve ever done the WSJ puzzle! I’m glad you can relate to that sense of accomplishment.

  3. Lisa says:

    I too love crossword puzzles. Another great free source of puzzles are from the creator Brendan Emmett Quigley, on his website of the same name. His puzzles have appeared in the New York Times, LA Times, Washington Post, etc. He drops two new free puzzles a week on his website – a challenging themeless on Mondays and a slightly easier themed puzzle on Thursdays.

  4. Kelli says:

    Oh I love a good crossword! It’s been a joy to have my middle school daughter also complete the NYT mini every day- we compare stats with the leaderboard. It’s been a fun point of connection. We also have one of those daily NYT calendars with the crossword- different family members pencil in answers throughout the day.

  5. I’m a use a pen and work across and down sort, putting in answers that may or may not be right. My husband is much more careful, only adding words when he’s certain . He also works a puzzle as words build in each other. The only online puzzle we do is the NYT crossword mini. We text our mini, Wordle, and Connections scores to each other (and I’m always secretly pleased when I’ve solved faster than he does.)

  6. Libby says:

    I enjoy crosswords but I’m not super great at them, even with an English degree! My grandparents, of the “greatest generation,” always worked the crossword in their daily paper. It was a habit. My grandfather would start it and hand it off to my grandmother. They would pick away at it and did not worry if they didn’t finish it. They were both avid readers as well. I credit my love of reading to them. They both always had a book going. My grandfather was a veteran and farmer and always found time to read.

  7. Janet H says:

    I can definitely relate to a lot of this. My day isn’t complete without (and usually starts with) Wordle, The NYT mini-crossword and regular crossword and then Spelling Bee, in that order. If my work day is particularly busy, then I purposely won’t start Spelling Bee until I have cleared a lot of my inbox (the torture!), as it is definitely a distraction as once I start, I can’t stop trying to think of more words! I also don’t mind if I can’t finish the main NYT crossword and use the app’s checker to help me get through more of it, I just like the process of trying to do as much as I can.

    My word puzzle appreciation must be genetic, as my dad also couldn’t finish a day without the NYT crossword puzzle, which he always proudly did, and finished, with a pen. He’d probably be disappointed at me not minding if I don’t finish, but I know he’d be pleased that I try.

  8. Mary Duncklee says:

    I used to do crossword puzzles all the time – usually in the little books. I now do Sudoku, Wordle, Connections and Twordsy (in that order) on my phone.
    I’ll have to try crosswords on my laptop now!

  9. Molly says:

    Several years ago, I got into the habit of playing the free NYT daily crossword online when I got bored in grad school classes (oops). I wanted to do them more often so my parents got me a subscription for Christmas. I filled them out whenever I had some extra time on my hands, but during the pandemic I got really into having a streak. I broke it a time or two but now I’m at over 880 days in a row! It’s such a fun and relaxing ritual at the end of the day. You’re so right that you learn so much random info from crosswords! I also love it because it makes me feel connected to my late grandma, who used to fill out the local newspaper crossword (in pen!) everyday.

  10. Cindy says:

    My brothers, sister and I are all puzzlers, like our mom was. She regularly entered a weekly crossword puzzle competition featured in the local newspaper. I don’t think she ever won the prize money but puzzles brought her joy.

  11. Rick OBrien says:

    I too like the Washington Post/ LA Times crossword puzzle. I like pencil and paper. I print a bunch of them off, put them on a clipboard and enjoy. On occasion I do the NYT crossword puzzles too. A good crossword puzzle makes you work a little, but not so much that you get frustrated. It has to be a bit of a challenge or what’s the point. Nice article, thanks

    • Leigh Kramer - MMD Editor says:

      “A good crossword puzzle makes you work a little, but not so much that you get frustrated.” That’s it exactly!

  12. Becky says:

    I also love crosswords, but only complete a little at a time and prefer going through a print medium. Any recommendations on a good crossword book/magazine to purchase?

    • Leigh Kramer - MMD Editor says:

      I hope someone else will chime in with a recommendation because I haven’t gotten a crossword book in 20+ years! I think most of them were gifts too.

  13. Jessica says:

    Crosswords are so nostalgic for me. My Grandpa Sam always worked the two daily puzzles in our local newspaper, The Tulsa World. He taught me how to decipher the clues, how to understand when the answer will be plural, or a specific part of speech. During my late teens/early twenties, when I was driving myself and had a key to his house, I would pop in randomly during the week to raid my Gram’s Dr. Pepper and Little Debbie stash, and I’d always peek at his puzzles and add answer or two as a little hello. The crosswords were where I first noticed the symptoms of his Alzheimers. Little mistakes at first, that I’d erase and fix. Eventually they became such tangled snarls there was no way I could be subtle about my corrections. “They keep makin’ those things harder and harder!” he said. Now, every time I get the newspaper (not often any more) and I fold the puzzle page into the perfect rectangle needed to see the puzzle clearly, I think of him and smile. Your routine sounds delightful! I’ve done crosswords on my laptop before, but pencil on newsprint will always have my heart.

  14. H says:

    I started doing crossword puzzles with my mother in law when we briefly lived with her a few years ago. My husband and I now work on a NYT Sunday puzzle just before we go to bed, and I do the free Atlantic puzzle almost every day – they get harder as the week goes on.

  15. Kim says:

    I just learned of a new nonfiction book called ‘The Riddles of the Sphinx: Inheriting the Feminist History of the Crossword Puzzle’ by Anna Shechtman, who is a crossword constructor for The New Yorker. It sounds like an interesting read!

  16. Anne Marie Vorbach says:

    I really wish that there was a way to do a crossword online and go back and forth with someone else. My daughter and I both love them and do the NYT together when we are together. It would be great to do that across the miles. I am thinking just passing it back and forth, virtually. Like I would do as much as I wanted to or could, then would pass it to her, and so on. Someone should invent this!!

  17. Lisa notes says:

    I used to love doing crossword puzzles, then I switched over to a major Sudoku addiction. 🙂 I try to never miss the daily online Sudoku puzzles with the NYTimes.

  18. For all your puzzlers, you should definitely check out the book, THE PUZZLER by AJ Jacobs. He researches all kinds of puzzles including crosswords about who creates them, plus the book has all kinds of puzzles to solve as well.

  19. Sue says:

    Crossword puzzles are a part of my family history, too. My dad always did the one in the newspaper everyday. Also in ink. Until the day he died, in his mid-90s.

    Have you see the short film entitled “Crossword”? I watched it on Acorn TV. Part of the Short Film Showcase, season 2. Only 13 minutes long, and worth a watch for crossword people.

    • Leigh Kramer - MMD Editor says:

      I haven’t seen it but this reminds me that I did watch the documentary Wordplay years ago and thoroughly enjoyed it.

  20. June says:

    We do the NYT mini every day with our kids! I love how much random knowledge it adds to our lives (also perfect for homeschooling 😉). Thanks for the tip about the WP puzzle being syndicated and free with an ad – we’re going to give it a try.

  21. Mary says:

    I’m not good at crosswords so I don’t do them often, but I do like word games. However, I find that whenever I try to make them part of my routine, they start to feel a bit oppressive — like one more thing on my long to-do list, kwim? I had to quit Wordle because it started to feel more like an obligation than something fun.

    It might just be my personality, but if anyone has any tips to avoid falling into this mindset, I’m all ears!

    • Leigh Kramer - MMD Editor says:

      You know, this is really interesting because I also have to find the right balance with adding things into my routine without them becoming oppressive. I pay attention to whether it continues to bring me joy and if it doesn’t, then I let it go. It’s okay if it only works for a season.

  22. Susannah says:

    Oh boy, do I love crossword puzzles! When you said, “[…]I had a phase of working my way through crossword puzzle books, doing one after another after another.”, my soul recognized a kindred spirit. I get on a dangerously addictive crossword kick when on vacations and *cannot stop*. On one trip I took with my family to California wine country, I spent most evenings crazily working through crossword puzzles in my beloved NYT Days of the Week Crossword Puzzles book (hello, Mondays and Tuesdays, we are bffs). I found it hard to read my book when we would all hang out in the evenings because we were prone to chatting, but with crosswords, I could be involved in the conversation every now and then without completely losing the plot, so to speak. I think I did close to 40 puzzles that trip, which qualifies as a lot in my mind because we also spent all day out and about, hiking, and drinking lots of delicious wine! The tiredness (and wine consumption, hehe) was no match, however, for the crossword fervor! 🙂

  23. Betsy says:

    I also include puzzles as my morning routine. My husband and I both nerd out each morning on NYT puzzles. We love Wordle and the fun word association game, Connections. Of course we also complete the Mini daily. We kinda make the morning a competition. Keeps us sharp!

  24. Melissa Sudfeldt says:

    Not crosswords, but word games! Every night I snuggle into bed and do Wordle, Connections, Waffle then Strands. It just comforts my brain and helps me settle. The only drawback is my colleagues do them in the morning so I can’t chat with them about hard/easy they were! But now I’m thinking crosswords might also be fun…

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