Word games and the joy of playing every day, with Lex Friedman
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Grammar Girl here. I'm Mignon Fogarty, and today I'm here with Lex Friedman, who does so many things. We're going to talk about word games. Lex, I have known you forever. Welcome to the Grammar Girl podcast. Thank you. I'm very excited to be on the show. Thanks for having me. Yeah. The reason I know Lex is that he was one of the co-founders of Midroll, which has been our advertising partner since the

I think the beginning or almost the beginning and people don't realize, but ads really make the show possible. So Lex, like Grammar Girl is possible because of your work. I mean, it's here today, largely because like in part, at least because of you. So thank you. That's very kind, but it also always succeeds because it's a great show, but I'm happy to have played a part.

Really, you've been there a long time. And so now you're out on your own and you have so many fun projects going on, including a site that updates daily word games, which is what we're going to talk about largely today. So can you just tell people about your word game site?

Yeah. So the site is Lex.games because I was very creative when I named it. The origin story was I loved when the New York Times first launched its connections puzzles and I thought they were really fun and I wanted to create one because I was trying to think, how do you, how do you create one of these puzzles? Like what's the thought process behind it? And I found a website where you could do it. And I made a couple and I was sharing them and people liked them. And then I made one that had a typo and that website that I was using had no option to edit things. I was like, I should build my own. So

So I built my own site because I had a web developer background. And so I built my own site to build my own connections puzzles. And I was posting them every day. I was like, now that I have my own site, I can post these every day. And I was doing that and people kept playing them every day and sharing their scores. And I thought I could launch some other word games. And so I created a second word game and a third word game. And at first they were all living in different places. I said, this should all be one thing. So I created the site and the app Lexot Games and

it has grown to a total of nine games, depending on how you count that I'm publishing seven days a week, every day. And oh my gosh, it's crazy. And it's not even your full time job. I mean, I love the fact that you can you can manage this. Do you write all the games yourself? I write all the puzzles myself. There are a couple puzzles that can write themselves, which is great. So I have a

One of my favorite games is only on the phone. It's not on the website. But in the iPhone app, there's a game called Letter Opener, where it gives you two or three letters. They change each day. And you have to make as many words as you can within 90 seconds that start with those letters. And a lot of it is actually about how...

Not just how good are you at thinking of those words, but how good are you at typing on your phone? In my case, not very. But that game builds itself. It looks and sees how many words, you know, if I pick three random letters, how many words can I find that exist that start with those letters? And if it's enough, then it uses that as a potential puzzle.

So there's a couple like that that can make themselves. But for most of them, there's a lot of creativity and puzzle construction involved. And so I try to do it in batches. Currently, all the puzzles are good, you know, about 30 days from when we're recording. And as it gets closer to that time running up, then I spend another couple of days hurriedly creating as many puzzles as I can.

You are farther ahead on your games than I am on this podcast. That's for sure. It's by necessity. Because if you wait too long, it's really... First of all, the app crashes if there's no puzzle ready for it to go. And then people are now used to it every day. Far and away, the hardest thing is having a full-size crossword seven days a week. That's...

I probably shouldn't have done it when I first launched it. It was one a week. Now that there's one every single day, it's a lot. Those take a while to put together. Do you play the games yourself or is making them sort of the game for you? Because there are some that can make themselves, I get to play those. And so in some ways, those are my favorite because they're ones that I can play too and I love word games.

I do play test all of them every day. So I go through all the games each day just to make sure that they're working. Sometimes I can catch a typo or whatever. So my version of connections, again, I don't know why this, I actually, I know exactly who to blame. A good friend of mine who I co-host a podcast with, Dan Warren, when he saw me making my own connections puzzles, he suggested I call them collections.

So my puzzles are collections puzzles. And I do like to check those every day, the day before they go live, because I don't really have an editor on my own editor. So looking at those, I can usually catch everything, but I play through them each day just to make sure that they're good. But I don't, I don't rank on the leaderboard because I think that would be unfair if you made the puzzles and then ranked at the top of the chart. Yeah.

And you mentioned typo. That was going to be one of my questions. Like, do you get hate mail when you have a typo? I interviewed an editor of a knitting magazine once and she said she got death threats when there was a typo in one of their patterns. So I hope it's not that bad. People are eager to tell you if you made a mistake. And I think most of it in my case comes from a good place. It comes from people wanting me to be aware.

And I appreciate it. I will tend to, it's a reminder sometimes of how popular the games can be. Because if you wake up in the morning and people maybe in Europe who are playing these games by 6.30 in the morning, my time, have sent me 15 posts on various social media networks about a typo. It's at least reassuring to know that people care enough and see it. So if I can fix it early enough, I don't feel bad. If I don't see them until later in the day, then I feel pretty guilty. Yeah.

Yeah. One of the people asked, you know, I put out a call on social media for questions people might ask. And someone said, well, I don't know who he is. Why would I play his games? And I thought, well, you know, I think one reason, I mean, one reason that they're fun, but another reason is that you're quite accessible as the creator. You know, people can communicate directly with you.

You know, as a it's kind of tangential to our conversation, but I am I'm somewhat challenging to Google these days because there is another person who also works in podcasting who has the same name as me and frankly, of whom I'm not that fond. But I you know why the reason I was comfortable putting my name in the game's title is because I do try to let at least some of my personality shine.

shine through these puzzles. I have said in, I think in the app description, you know, you might see more than the normal amount of references to the music of Weird Al Yankovic, or they might be giants or Apple or other things that interest me. And I do that intentionally because I think it's, although some of my puzzles, like I said, were inspired by the New York Times or by other great puzzles, I'm not trying to just make alternate versions. I'm trying to make, you know, myself infused versions. Right.

Right. Yeah. Someone on Mastodon asked how many references to the Philadelphia Eagles are in your puzzles. Oh,

I would say, as they are my favorite football team, they probably show up a couple times a month because I have a lot of puzzles to choose from. Right. So sometimes, you know, what's really fun about making the connection style puzzles is sometimes, you know, again, I publish them. I write them a month, sometimes two months in advance, and then I'll play the New York Times each day. And sometimes I'll see that they have the same set that I have coming up in a couple days or that I just had a couple days ago. And that's going to happen.

But we both of us have done a thing where I don't remember exactly whether it was like Eagle, Cowboy and Ram and Bill. And you had to identify that those were all potential NFL players. So if I'm ever going to use clues involving the NFL, the Eagles will undoubtedly play a role. Yeah.

I would probably not get any of those. I'm not a big sports fan. And that leads to my next question. So, you know, I'm curious about the kind of stats you get on the back end. I know there's a leaderboard. And really, I just want to know if you can see how badly I'm doing. Honestly, it was one of the most common questions. No, I don't see anybody's individual scores.

And the most interesting thing to me, I guess the first one is sometimes I think a puzzle day is really easy. Like maybe I made this collections puzzle too easy and then people really struggle with it. So sometimes things that seem obvious to me aren't obvious to people. And the opposite happens too. Sometimes I think I've really got a hard one and people crush it. But the thing I've learned the most from looking at the stats and looking at how people play is, I think I wrote an article about this somewhere too, but

Finding the right difficulty level is probably the hardest thing. I've been doing this now for a year and a half and I'm still learning it because people want puzzles to feel hard. They don't want to feel like it's a gimme, but they also want to be able to solve it. So too hard is not fun. And finding that sweet spot of, I feel smart because I solved this, but it wasn't impossible and I could solve it is tricky.

I know I feel frustrated when I don't solve the New York Times' connections puzzle, which used to never happen and now sometimes happens. And I know just how bad it must feel for my players when they have the same problem. So I want them to be solvable. And, you know, my son plays each day. He is 13 and he is not often, but more frequently than many, one of the bottom ranked players on collections. Because if he doesn't know it, he'll just start guessing random patterns until he solves it.

But I don't want people to need 40 guesses to solve my puzzles. I would like it to be a little bit more doable. So that's the most interesting thing to me. And I think I've gotten better at it, but I still have room to grow. Have you seen any patterns in the stats of what makes something too hard? If the clue format of two word phrases that all start with the same word, let's say, or end with the same word. So like, now I won't be able to think of any, but like coffee pot or coffee cake and

you know, whatever, coffee house. If you pick the right ones and they're all really common phrases, people get them right away. When I do puzzles, which I have done more than my fair share of, where I list multiple possible answers that could pair with coffee, people are not patient enough to see, hey, there's five or six or seven words that could pair with coffee. Let me see what else these others can be grouped in. They just want to figure out coffee. Like they see the coffee is going to be one and they go for that one like crazy. And then their scores get bad and then they get frustrated.

So I thought that was the fun slash clever way to build those, but it really frustrates people. And I don't want to frustrate people. I don't like when word games frustrate me. So I've tried to, I'll maybe put five potential options for a set of four, but I won't put six or seven because people tend to lose their minds. Yeah.

Yeah, no, that was the one I struggled with yesterday. It was blank table. So it was bridge table, coffee table. And yeah, I got a couple of guesses before I got that one. Yeah. And so what is your background? I happen to know that you have a degree in linguistics, but did you love word games when you were a kid? Sort of what's your background with respect to words and word games? My parents would always do the Sunday New York Times crossword puzzle. And it was a family affair because at that point,

I think the Sunday crossword puzzle is easier now in some ways because I think it's easier to solve crosswords in an app versus pen and paper or pencil and paper. But it was always in pen and it was always available to anybody. So like if my father went first, he would fill in whatever he could and then my mom would go and then it was my turn and I could do all the ones that were things that they didn't know about that were more kid friendly. But I always loved the jumble and I have a sort of jumble-esque game now that I do.

So I would always look at them. Sometimes they were far too hard for me. It was much more, my wife has always been a huge puzzler. And honestly, she taught me early in our marriage, so more than 20 something years ago, she taught me how you're actually supposed to solve crossword puzzles. And she taught me the same way Scrabble players need to know all the two letter words. When you're a crossword solver, you have to know all the three letter words and all the different clue formats and what it means when there's a question mark and what it means when they have abbreviations in the clue. And so she really got me better at solving those.

And then she and I both became obsessive and we each have our own New York times game accounts. We can do those each day. I play LinkedIn's puzzles each day. There's a site called Puzmo that I was inspired by that has a lot of daily word games. And I sometimes have to limit myself. I can't take on too many more word games. My, and for that same reason,

I haven't launched more word games. I have a couple different concepts of word games to share, but people have told me that they feel, boy, I'm almost overwhelmed by the number of games on your site. I'm like, you don't have to play them. You can just play the ones that you like. It's okay. I'm not offended. But people feel that sort of sense of completionism. So I've been hesitant to add more. Yeah, that was a question multiple people had is if you're going to add more games. But I do feel that the way you're describing, like there's so many already. I often feel like I don't get to them all or I shouldn't. I think...

Realistically, any games that I add, I would have to be able to make themselves, which limits the creativity behind the game. Not what the concept of the game would be, but I don't think that I can budget more time to authoring games because, as you might expect, it's a lot of time. Some of them I can create anywhere. Sometimes I'll be playing the New York Times' Connections puzzle, seeing a connection they didn't use and think, I want to do that. So then I'll go switch tabs on my phone and make my own puzzle right then.

The crossword puzzles I have to do at a desktop computer. There's an app that most crossword puzzle creators, I think, use these days called Crossfire, which is not a great app, but is very good for what you need it for. But like, I can't make those on my phone. But I spent a decent amount of my life making puzzles and I don't think I can make more creative ones on a day-to-day basis.

Yeah. And Conlections is pretty much the same as Connections from the New York Times, but I appreciate the little twists on a lot of the other games. So, you know, your wordle is, it has a little difference to it and the word jumbles are a little different. So explain sort of how these puzzles are different. Yeah. So like you said, Conlections really is the same concept as Connections. The biggest difference there is you have unlimited guesses. Yeah.

which some people love and some people hate. I know that I sometimes wish I could get one more guess on connections, but this way people who want to solve it can. If you want to give up, you can always do that and just have it reveal the answer. You mentioned my version of Wordle. I created a game called Six Appeal, which really is Wordle with six letters. There are other people who have done similar things. And what I found, especially early on, when you're coming from Wordle and you love Wordle and you go to a game like Six Appeal, your brain isn't necessarily primed to come up with six letter words. Like Wordle is a perfect game.

And I would never create my own version of it that's a knockoff because it's perfect and I celebrate how great it was.

and is. But with six letter words, sometimes it's hard to think of some that fit the model. So I built it where it has a key rule difference from Wordle, which is you don't have to guess real words. So some people play it a little bit more like the classic board game mastermind, where they just use whatever letters they want to figure out what letters go where. You get more points if you use real words for each guess, but sometimes I don't, I don't know the answers to that one each day. And so when I play it, I try to use real words. And if I get some, I'll just use the jumble of letters that I need.

You also referenced my word jumble game. I'm very proud of that one because a lot of my games were directly inspired by existing games, which I credit on my site. But buy a vowel was just an idea that came to me in, I don't know, not even in my sleep, but I just was thinking about games. And this one kind of came pretty well for him. That's B-Y, a vowel. So you have five jumbled words and each one is missing one of the five vowels. And you have to both unjumble the words and figure out which vowel goes in each word.

And they're all loosely themed in some way. Like there's some connection between all the words to help you solve them. When I first started building that puzzle, it was all five letter words. It was a little easier to solve. It was a little bit harder to create. At some point I said, I removed the five letter limitation from myself and

And I make sure there's always at least one five letter word because I think that's the way in a lot of the time. Like I'm looking at as we're recording what today's is and I can see there's the first one that's because they're shuffled each time. But I have T-O-B-D. Now I built the puzzle so I do know the answer. But if I can figure out that that word is doubt, then it starts to all these words are going to have some relation. And so the other answer is today. Since nobody will hear this day, we're not really spoiling it for anybody. Like anxiety and angst and fears. And so they all have some kind of connection.

That one's really fun to make. And there are times where I'll just be sitting at the kitchen table and I'll say to my kids or I'll say to my wife, hey, what's a word that has a U that means, you know, in pain? And somebody else is like, suffering? That's good. And they know exactly why I'm asking because sometimes you just need that other word. The theme really helps. It helped me yesterday solve it. Absolutely. My favorite game is actually Lexicox. And I don't think I've seen that anywhere. Maybe I don't know about it, but is it completely...

original or is it based on something? No, it was inspired by, there's a site called Puzzle Society and they have a game called Seven Little Words. So this is, I mean, I have seven words and they, it's the same concept, right? If you have seven, what I consider sort of crossword style clues, and then a bunch of chunks of words below that you have to assemble into the words to solve all the words above. And Seven Little Words is a fun game, but there it's not themed.

And I thought it would be fun if somehow these were themed. And the very first one I created, I made the clues themed as opposed to the answers themed. And it happened on a whim just as I wrote it. And that's been my general approach to all of them ever since. It doesn't rival the popularity of collections. It's still a little bit less popular than collections. But it's the one that I think people enjoy it more. Because in some ways, it feels more solvable. The hints feel a little bit less defeating to take.

And as in collections, there's only four answers, right? So if you take a hint, then you've had a lot of it solved. But I love making those. The tricky part there is coming up like you need some words that are the right length. And I like to use often the same clue more than once to mean different things or to clue different words. And people are very quick to let me know if I have done so where the answers are exactly the same length. Because I'll tell you, here's this clue. Like today, I'm looking at one that says sorted 12 letters.

If I had a second clue that was also sorted in 12 letters, you wouldn't know which one is which. And some people like to solve them in order because you get a special little mark by your score when you do that. A star. So, but I love making those. And people, yeah, people, that's definitely my second most popular game. Yeah. And the other thing that was nice about that is you can make your own game.

That's right. It's, um, that's currently limited to people who become paying subscribers. Um, and you can play almost all the games without paying. The only limitations for people who don't pay are they can't do the full size crossword. And then there's random versions of certain games, like just infinite versions of certain games that they can play versus just the daily one, uh, and then creating their own puzzles.

But everything else is free and there's no ads because nobody wants to see ads when they're playing games. I get that. But yeah, my son will actually make some for the family from time to time and it's pretty hilarious. Yeah, no, it'd be really fun to make some for friends with a specific theme for like a party or a birthday or something like that. I actually had a friend who not

Not a friend, sorry, a stranger who wrote to me who wanted to gift his mom a membership to the site and I hadn't built support for gifting memberships. So we worked it out directly and he created his own lexicogs puzzle for her to reveal that that was what her gift was. It was very cute. Oh, very meta. Yeah.

You know, you mentioned that just from a technical standpoint, you mentioned that you can play things that aren't words in the Wordle type game, Six Appeal. And, you know, I happen to know like making word games, you generally license a dictionary as the backend for the game. So, you know, can you say which dictionary you've licensed? And then how does that work when people are guessing something that isn't a word? Yeah.

So I found a free dictionary. I'm sorry, I don't remember which one it was, but there were some open source free crowdsource dictionaries. And I experimented with a few and found one that I liked. I will say it has some typos in it, right? It has some non-word entries in it, which are a bummer. And I built a tool at one point that I still use from time to time that just takes a random six letter word from that dictionary.

and puts it in front of me. And I can say, is this word common or rare or wrong? And it almost feels like a game because you can get kind of mindless of real word, not a real word, typo, whatever. And I did that because if Six Appeal comes up one day and it picks a misspelled word, since I don't curate what those words are ahead of time, people are going to be really grumpy, right? If they try to solve the word and then it's not a word. It did happen one time. I had one typo word that slipped through and people were quick to let me know about it.

But I've gone through now and it's only allowed to choose words that are verified. And I verified thousands and thousands of six letter words and there's more to go, but there's enough that I don't feel as much pressure to do it. So I still do it when I have total brainless downtime. How long have you been doing this? So I just noticed that yesterday as we were recording was my 300th mini crossword, but for collections, I've built 495 of them. So I've been doing it for about a year and a half and

And then the actual Lex Games site launched when I put all of them together. I'm not stalling while I look it up. Don't worry. That's okay. It's actually just shy. No, decidedly shy of you. It was 246 days ago, according to this post. So I guess I launched the site. I'm sorry. That's when I launched the app. I launched the app May 15th and I launched the site about six months before that. Wow. Wow. What has surprised you over time as you've been doing this? So the...

Honestly, one is a selfish surprise, which is I had never made an app for iOS before. And I honestly, when I started, wasn't sure I'd be able to do it because that's just not a skill set of mine. And I pulled it off. So I was surprised that it worked. It also, I will say, it surprises me how the way these games grow has evolved because

There was a time when everybody posted their Wordle scores on every social network. And then there was a backlash to people posting Wordle scores. When I started launching mine, especially my collections puzzles, I would get literally as many as a hundred or so responses on social networks each day with people's scores. And they would write to me. So people weren't as mad because it didn't necessarily infiltrate their feeds, but then other people loved it because they could see who else, like what order people solve things in or which one stumped them. And yeah,

And over time, especially once the website had leaderboards and once the app was out, people don't, it's very rare that people send me their scores. I get one or two people who send me their scores a week. And it's been interesting. And I still see people who tell me they miss that part. They loved seeing how everybody else scored versus not being able to see it. And it's interesting to me that there were a lot of strong opinions about that. Like people did find it a little bit noisy in their feeds, which I understand.

And then that other topic I mentioned earlier of what difficulty level people really want. That's been the other surprising thing because I,

You don't think about it until you're making puzzles. I certainly think about how annoyed when I can't solve a connection puzzle or for a while while while Will Schwartz was was out the New York Times crossword editor. I thought that the Saturday puzzles got not fun. I thought they got too hard for the New York Times and I was frustrated in the week he was back. I thought it was more fun. And so I'm very conscious of that when I'm making puzzles of trying to make sure it should be challenging, but it shouldn't be shouldn't be frustrating. And they're very close together when it comes to puzzles.

Yeah. Do more people play on the app or on the website? It's a great question. It's almost about two thirds on the web and one third in the app. But the app is newer, right? So you had this group of people who started with the web probably. Exactly. And there's some people who prefer an app for this kind of thing. And some people prefer a website and...

I'm happy to support both. It also helps me not give into the pressure to launch more games that I would have to build it in two places. Yeah. I had a word game many years ago. It's not available now, but it was called Grammar Pop. And one of the challenges every time there was an iOS update was

then we had to update the app. Are you running into that problem or did you build yours in a smarter way? Well, there was a time when, you know, I have to be on the betas, the developer betas when Apple's going to have new versions of iOS. And there was a time when it absolutely broke my app. And then I had some early adopter friends who wrote to me right away, hey, it doesn't work.

And I said, it is an Apple bug and I might have to work around it. But I'm going to see if they update it. It was one of the early beta release. I'm going to see if they fix this before I have to. And I wrote to Apple through the right channels to say, hey, this is how this is behaving. They shouldn't. And I was very pleased when the next update came out of the beta OS and it corrected that issue because I did not want to have to work around it. But so, I mean, I have to do a couple things and I've certainly made the app better. That's actually another surprise was that I heard from people who...

with accessibility issues. You know, especially visually impaired folks who were asking for certain things to work differently. And so I had to learn a bunch more stuff, especially about how voice control on iPhones work. I don't know if you've ever turned on voice control. It's available on everybody's iPhone, but it literally, you can not look at the screen and touch it. And it'll tell you like, here's what you've tapped on. And then if it's the thing you want, you have to press again to say, yeah, that's the thing I want. And I had to do some work to make sure that the game could tell you, you have now solved this connection, right? Or you have now solved this word and

And building all that support was a very new area for me, but I was happy to do it. Oh, that's wonderful. We had a question about accessibility. I was going to ask that next. And I've tested it. I actually tested it recently on my computer. I didn't know you could do it on phones too, but I mean, of course you can, but that's great. So your games are even accessible.

Yeah, I mean, it's and I wouldn't have done it because I wouldn't have even thought about it. Right. Had people not brought it up. And it's funny because sometimes people write to me and early on when I was adding some of those features, they said, hey, the way you did this is actually slightly annoying. Like it's talking to me too much now. Can you have it talk less or make the message briefer? Which, of course, made total sense. But I didn't know. So it's it's come a long way.

Oh, that's fabulous. Well, tell people, tell people, remind them again where they can find your games. Yeah. Just go to Lex.games. It'll link you to the app if you want, or you can play right there on the web. Lex.games and a .games domain. I didn't even know existed until I registered one. Nice. Well,

Well, Lex, that's our discussion about games today. You do so much more. I want to talk a lot about a lot of that in the segment we're going to do for Grammarpalusians. I want to talk about the songs you make with your son, Liam, which are just adorable. You have a game show that I actually enjoy called...

What's it called? Friendly competition. Yeah, friendly competition. That's a lot of fun. Also game related. So we're going to talk about and your book recommendation. So we're going to talk about a lot more in the segment that our Grammarpalooza supporters get. But for everyone else, thank you so much for being here. Lex, thank you for being here. It's been a delight. Thank you. I've loved it.