Monday Roundtable: The Board Games We Never Lose

There are just some things some people are good at: spelling, thinking of synonyms, remembering numbers, dark magic, imaginary capitalism. And some times those things translate into being very good at board games. This week we asked our team what board game they always win, and here are our answers. Let us know if you think you could beat us — or what game you always win — in the comments!

Heather Hogan, Senior Editor: Monopoly

I hate to say this because it makes me sound like a monster but I am truly unbeatable at Monopoly. Part of why I always win is because I’m shockingly ruthless at it. I made a grown man cry on Christmas Eve a few years ago because I humiliated him so thoroughly, making him mortgage all his properties one-by-one and count out his money to me, slowly and deliberately. (Shouldn’t have been rude to my girlfriend, motherfucker.) Part of it is my ability to see three to five moves ahead for every player: Where you’re probably going to land, what you’re gonna get from it, who’s gonna want it, what you’re gonna want from them. It is an evil way to use my intuition, I know. I think the biggest part of my success, though, is my uncle gave me a Monopoly probabilities booklet when I was just a kid and I studied that thing more than I ever studied for school. Seven is the most common number rolled with two dice. Jail is the most likely space people will land on. The orange properties — New York Ave., Tennessee Ave., St. James Place — are, therefore, the most likely properties people will land on, and repeatedly. The reds are the next best, specifically Illinois Ave. due to dice probability and the fact that a Chance card exists advancing players there. Magenta properties are a little less probable but also cheaper to build on, which means a quicker return on your investment. Greens and dark blues are a waste of your life. I like Monopoly because I am good at it and very competitive and I like to win, and unlike a lot of other board games, it relies on your skills as much as it does on chance.

Rachel Kincaid, Managing Editor: Boggle

I am amazing at Boggle. Other seemingly word-related games are deceptive in that what they measure is not actually verbal — Scrabble is really more about the ability to maximize points strategically, crosswords are kind of more about knowing trivia, etc. Boggle, though, is just about seeing words and writing them down, and I guess maybe sort of pattern recognition if we’re getting technical! And I know a lot of words, and am good at writing them down. And that’s it, that’s the entire game. I haven’t played Boggle for years; it was really only played with my family when growing up, and for a short period of time when I used to babysit this one particular child who insisted on playing it every single time even though I did not let her win, and was in retrospect a little too competitive. It’s fine I’m sure she’s fine.

Carrie Wade, Staff Writer: Password

Password, a la the ‘60s game show. My family did Game Night at dinner for a while when I was a kid and my dad and I were basically a superteam at tabletop Password. We haven’t played in well over two decades but I am confident we would remain unstoppable to this day.

(Related: We had to retire Game Night because I got too competitive.)

Erin Sullivan, Staff Writer: Bananagrams

I have a pretty solid track record with Bananagrams and Connect Four lmao, and I love me for chosing two games that for sure don’t have boards. General area though! Connect Four always seems to be at bars, which is why I know this about myself, not because I own Connect Four and encourage other adults to play with me. And then everyone seems to own Bananagrams, yeah? Currently, there are two sets in our two-person apartment, and I wouldn’t rule out a third mysteriously appearing in the near future.

I have a very fast and loose approach to Connect Four and very chaotic energy while playing. People hate that I just willy-nilly drop in chips as if I’ve not one thought in my head (I don’t), and I think this is key because it can even rattle people who are great at strategizing. With Bananagrams, it’s about one big word to start and breaking off into smalls. Definitely not trying to impress with interesting words, and I’m gonna hit you with that “has” and “none” and “can” until I win. Ultimately, though, no one really wins, because to have won you’ve had to scream “peel” on repeat until everyone hates you.

Creatrix Tiara, Staff Writer: Monopoly

I feel like I always win Monopoly? Though I don’t normally go in with any sort of strategy. I’m mostly sharing this though because I wanted to talk about this one time my friends and I were at some guy’s house & we were playing Monopoly & my other 3 friends were making out with some guy each and meanwhile here I am drunk on tequila being THE STRICTEST BANKER EVER. Like “STOP KISSING YOU OWE THE BANK $200”. Tequila, me, and Monopoly don’t mix.

Alexis Smithers, Staff Writer: Scrabble

SCRABBLE I actually haven’t played scrabble in years because my family won’t play with me anymore (because I was like seven or eight playing with my aunt and cousin and I put down “way” and they were like “Good job, Lex!” and I was like, “I’m not finished.” it turns to “away”, “Good job, Lex!” / “I’m still not finished.” turns to motherfucking RUNAWAY ON TRIPLE LETTER SCORE THE GAME NEVER OFFICIALLY ENDED THEY JUST LEFT ME THERE TO THIS DAY I AM STILL PROUD) and after listening to Back to Back where Cameron Esposito talks about lesbians and board games, I’m thinking it’s for the best that I don’t try it with anyone not blood related.

Al(aina) Monts, Staff Writer: Chess

I always win at chess because I only play chess alone because I’m a really bad chess player.

Riese Bernard, Editor in Chief: Scattergories

I am really really really serious about Scattergories. Nobody appreciates my adherence to the rules. Honestly I don’t see why the rules are so confusing to people, but maybe it’s just sad for them that I always win.

Valerie Anne, Staff Writer: Scattergories

My family and I used to get in really heated games of Scattergories. It was great because anyone who was old enough to write words could play, and it was fun for everyone because even when you were bad at the game, it was pretty hilarious. There would always be fighting about semantics and my mother would always accuse me of being more lenient with others than with her, but I almost always won. To the point where now my family refuses to play with me because I’m a “writer” and have such a “big vocabulary” that I have an “unfair advantage” but really they’re all just sore losers.

Carolyn Yates, Staff Writer: Settlers of Catan

I win often – but not always! – at Settlers of Catan, because in high school instead of branching out socially or really going outside I played it almost every single Sunday afternoon with my then-best-friend and her family. They had expansion packs. They had expansion tiles someone had bought on ebay. They had extra leaves to put in the kitchen table. We regularly played to obscenely high point counts in brutal, tea-fuelled six-hour games and I lost constantly, with the side effect that now when I play in casual settings on a regular-sized board with friends I sometimes get to win.

Yvonne Marquez, Senior Editor: Dixit

Have y’all ever played Dixit? It’s a strange little board game that’s super fun! The simplest way I can describe is that it’s similar to Apples to Apples but with pictures. You have a card and you say a word or phrase that reminds you of the card. Then your opponents have to pick a card from their own hand that matches what you described and then you shuffle up the cards and then everyone has to guess which one is actually your card. It’s a game that tests how well you know the people you’re playing with, their quirks and how their mind works. I seem to win most of the time and I think it’s because my Scorpio moon is really good at reading people and their intuitive feelings.

KaeLyn Rich, Staff Writer: Ouija

I honestly can’t think of one board game that I always win, unless you count the Ouija Board which is sold as a board game and also maybe is not a board game, but anyway… I grew up in a rural area with the local cemetery right behind my childhood home. I believe in ghosts partially because of growing up in an old farmhouse near a graveyard. I had some weird experiences in my childhood home. I believe in science, too, though, so I’m not sure whether my successful Ouija board sessions came from my own subconscious via the ideomotor effect or something more…spirited. I had a very close connection with my board as a tween and was convinced I could sense spirits in my house, so I definitely believed. This is going to make some of ya’ll yell at me, but I slept with the board under my bad at the peak of my obsession and played every day by myself. My friends marveled at how my board “worked” possibly because I really, really, really believed and made sure no one was intentionally pushing the planchette. I don’t know how one “wins” the Ouija Board game, but it was originally sold as a board game and Hasbro’s sticking to that category, so…I’m saying it counts! Also, I’m not particularly consistently good at any board games otherwise. I’m more invested in having fun and being silly than winning at a game, which actually makes the Ouija Board thing make sense, I guess.

Sarah Sarwar, Business and Design Director: First Time Everything

The first time I ever play a board game, I win. It doesn’t matter what game or where I’m at or who the president is — I AM WINNING THE GAME AND YOU CANNOT STOP ME. Train Dominoes, Monopoly, The Game of Life (oh ha ha!), and more — beware of challenging me to a board game that is new to me, for you will lose.

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  1. I’m generally quite good at board games, but I don’t have any that I win every time. I am jealous of those that do. It feels like a superpower!

    I can tell you that my 84-year-old Grandma still kicks my ass at Chinese Checkers. I’ve never beaten her in my entire life. I don’t get it. It’s a game of logic, but she is one of the least logical thinkers I’ve ever met (for example, she recently told me she would rather encounter a bear in her yard than a rat, because rats are gross, but she was pretty sure she could out run a bear). Apparently crushing it at Chinese Checkers is her superpower.

    • Your grandma sounds awesome. Whenever my mom (age 73) visits we play a whole lot of Demon (competitive Solitaire). I am finally at the point where I win a decent amount of the time. After playing her for ~35 years. Of course, she learned it from _her_ mother, who I’m not sure I ever beat. I do win when she teams up with my daughter, because she’s a teacher and a good sport and a doting grandmother so she makes sure Kiddo is really included and that slows her down. (Muahaha!) Of course that means someday Kiddo will kick my butt…

    • I would call myself a logical thinker and your grandmother is 100% right. Bears mostly don’t want to mess with you and you’d be fine, but a rat is a sign of the apocalypse.

      To bring this back around, I hate ‘would you rather’ games but this was an easy one ;)

  2. in honor of erin I’m going board-less board game, but I am the fucking champ of Taboo. I always make my friends play it on game nights and I can’t believe they still tolerate it. I haven’t told her this but one of the key perks of spending so much time with my roommate is that we’ll become a truly unstoppable force. taboo also has the perk of being able to blame your less excellent team members whenever you lose, not that I know how that feels. (wow I sound like an asshole, but I’m just really committed) I feel a real kinship with all of you equally competitive and committed board gamers, thank you.

    in general I am *too competitive* and if my family wasn’t also so competitive and desperate to see me lose, we would have definitely stopped playing games together by now.

    • The best Taboo story I know is my friend and her sister as a team.
      Sister: “You need one of these.”
      Friend: “Straightjacket!”

      … Spot on.

  3. DIXIT! I played it once like 8 years ago with people from college that I don’t see anymore and always wanted to play it again but didn’t remember the game.

    I always win at Bleff (I don’t know if there’s an American version with a different name), which consists of people taking a card in turns and choosing one word from it (they are all very obscure words from the dictionary) and having the other players write down the word’s definition. If you know it, you write and if you don’t, you bluff and write something that seems possible. The one who chose the word reads all the players’ definitions aloud along with the real word meaning and then people vote on which they think is the legit meaning.

    You get points for choosing the right definition, but you also get points for each vote your definition gets. Meaning sometimes writing a seemingly legit definition is worth more than knowing the definition in the first place. I love that game because it plays to my strengths, which are words and mostly bullshitting through life.

    • This is very similar to Balderdash, and Beyond Balderdash (same concept, but in addition to words/definitions, there are also categories for initials, dates, movie titles [you write a description of the plot], and people), both of which I love to play, but rarely find others who are up for it!

    • Balderdash or we always just called it “the dictionary game” and played with a dictionary you’d open to a random page and point to a random word til you found one nobody knew. Because we were the kind of family with like seven dictionaries. We also awarded points for eliciting hysterical laughter. There’s a version with proverb completion too.

  4. Since I was about 12 I have usually played boggle where everybody else has a three-letter minimum for words, and I have four letters, to make it more “fair”… and I still win most of the time.

  5. Scrabble is very much a pride thing (lit nerd, English PhD dropout, etc.), and also something I was historically good at since my senior year AP English teacher would let us play Scrabble on chill days and taught us all the 2-letter words and really weird-ass words that you can get away with that most normal people don’t know about.

    THAT SAID. This game has DESTROYED relationships. There are just too many people I can’t play it with because we all know that we will fight. And also my super STEM-minded engineer ex is the one person who always beat me at Scrabble (for like, 3+ years running) and my ego still hasn’t recovered. Am I even good at Scrabble anymore? I don’t know.

    • I feel like I am a walking contradiction because my parents love Scrabble, but I–also a lit nerd and humanities PhD student–hate Scrabble. I think it’s because people expect me to be good at it and then I’m not. Family made fun of me until I met my partner who also loves lit/has a master’s in English and also hates Scrabble! This prompted my mom to say, “Well she doesn’t like Scrabble because English is not her first language!” Which is not really true–she’s from South America but lived in the US for the first 10 years of her life, so she’s pretty perfectly bilingual–but my partner LOVED that excuse/thought it was hilarious.

  6. DIXIT IS SO GREAT!!! That’s how I always describe it too, Yvonne, like Apples to Apples except with pictures (and better than Apples to Apples, because I think I am the sole human being who doesn’t like that game. I seem to never be on the same wavelength as everyone else in terms of senses of humor–but I crush at Dixit).

    • That was I think the only game I hadn’t heard of and it sounds so good! I like the idea of a visual imagination game.

  7. I fucking love Scattergories and always get way too into it and end up winning by a landslide, lol. I played it just last week and for the letter P and category “things that grow” I put “penises” which I am irrationally proud of. (“Plants” was just too easy.)

    • So a question about the rules. Could you add a relevant adjective like piqued for an extra point?
      Or do the alliterative words have to a be a common paring like Peter Pan? (which is an obvious fail, since he never grew up)

  8. I’m not particularly competitive, I think the only game I’ve felt particularly at an advantage with was the Trivial Pursuits 1983 genus edition because I just sat and read all the question cards one day.

  9. I can’t remember the last time anyone would play Scrabble with me, so I’m not sure if I’m still Queen of the Tile.

    • Same and I really would love to play irl!

      I’ve been playing on and off online but feel like playing in person is different.

      • Also currently my highest scoring word online is “Dastard” (at 82 points, although I got 95 points for another, less entertaining word in a local game) and honestly I kind of don’t want to beat it and have it change.

        • Damn. Felt compelled to play a game in the first time since who knows when and promptly replaced Dastard with the much less interesting “Teacarts” for only a few points more.

          Okay. Embracing the teacarts. Maybe the chocolate frogs will help.

  10. “Games I Always Win” overlaps 100% with “Games No One Will Play With Me Anymore” and includes Bananagrams, Scrabble, Beyond Balderdash, and checkers. I can usually get people who have never played with me before to at least play the first three, but checkers isn’t really a game adults play, so I haven’t played that since I was 7, when my mom flipped the board off the table (my mom is great, I was being a brat at the time and kind of deserved it).

    I am very competitive (hence the flipped checkers board) and try to make sure not to brag/be annoying when I’m winning, but even if I am silent while we play, people get frustrated after I say “peel” the sixth or seventh time in a row, or strategically align my 7-letter word parallel to another to grab the bonus plus a few 2-letter words one too many times, so either way I end up not getting to play my favorite games very often.

  11. a) I want every staff writer to battle the other(s) who picked the same game.

    b) Mine is Taboo (well, it depends on the partner) and an obscure “Children’s Art Game” I got when I was eleven.

    The Art Game is a hardcore training for future art historians, artists and/or investigators, as you have to have an almost photographic memory, drawing and performing skills and a general knack for stupidly tiny details.
    Once upon a time I let my family play without me and it took them 2 hours to complete a 30 min (for me) game. (They were really frustrated afterwards. My “Rose Ellen Dix”- smug face didn’t exactly help.?
    Nowadays, as both art historian and general art creep I still profit from playing the game. I even used parts of it to learn for exams.

  12. The last board game I remember playing is (don’t laugh but it’s) Candyland. I’m an only child and I never had anyone to play board games with. I played video games and computer games a lot as a kid. When I got older board games were uncool and none of my friends played them so obviously I didn’t either.

    • Awww Ashley! Your parents totally shoulda played with you! (Says a parent of an only) Also your friends need to get a grip, only the bestest people play board games ;)

  13. Also, anyone else wanting to challenge everyone here to a game to see what happens?

    Anyone else wondering if that were feasible if it would be amazing or just the very very very worst idea ever?

    Anyone else wondering if they could win every game but trying not to admit it to themselves?

    • I was just about to say, I want all the Scrabble people to play a game but we need like other people to routinely come in and out to make sure we haven’t mauled one another.

  14. Ok I gotta mention Kinkopoly — rife has been working on it for YEARS and it’s finally in prototype!

    It’s kind of on the ridiculous silly fun side, which makes it really awesome to play with friends, though I’m kind of the earnest stoic type, sooooo it’s not so fun. BUT I figured out that if I play the “banker” type of character it’s way more fun — doing the admin of the game, reading the cards, being in charge of the different toys you can win, that kind of thing. :D

  15. I am amazing at Set. Once, when I was eight or so, I made a 16-year-old boy cry because I kicked his ass and then laughed at him. To this day, I am unrepentant.

  16. “Ultimately, though, no one really wins, because to have won you’ve had to scream “peel” on repeat until everyone hates you.”

    As someone who (almost) always wins Bananagrams, I feel this so hard.

    Also, Set. As a kid, I used to play by myself for HOURS at a time (even though it’s not a one-person game), so now I’m really fucking good at it.

  17. Probably no one else has ever heard of ENCORE! but I have dominated that game since literally forever. You draw a card that has a word on it and you have to A) think of a song that has that word in it and B) sing the part of the song that contains that word for at least 2 lines/phrases.

    We used to play it at family holidays and I was like 6 years old kicking the asses of every adult in my extended family to the point that we had to stop playing it because it wasn’t fun for anyone else (it was always fun for me.) Basically once I have heard a song a single time I will remember it word for word until I die which is only a useful skill for this one game but I’m okay with that.

    • I know Encore! I do not dominate it, as many of my friends were theater people (and good lord, the obscure lyrics they can call up) but I held my own enough to enjoy it.

  18. I am pretty good at taboo so long as I am not paired with someone under 24 because they don’t get some of the references I make or in one case wasn’t sure who Monica Lewinsky was(it was an early 2000s version of the game my friends have). I am also pretty solid at the board game Go For Broke, which the object is to be the first person to lose all their money gambling.

    Not a board game, but I am pretty decent at dominos.

    • Those look fun! Also the first one gave me a flashback to the highlight of my career of dubiously drivellish doggerel, when I composed a birthday limerick rhyming Ex libris with Phyllis and Sexagenarian bliss.

      • You may be a dastard
        if the board games you have mastered
        only please you when you’re plastered
        at the start –
        if when winning you say “me heart,
        don’t be angry now, my swee’heart,
        have a pastry from the teacart,”
        gleeful bastard.

        Doggerel? Check. Drivellish? Yup. Dubious? Ohhhh yeah. I intended to make it a limerick too but…this happened.

        • Iarrann mé, wonder I may,
          Whether your doggerel will dubiously slay.
          Is your attitude winning?
          Are our ambitions twinning?
          Devilishly drivellish dilemmas to weigh.

          • Be grateful – I deba’ed gleefully using the word deba’e as the final rhyme.

            Then felt that was a little too das’ardly, even if the teacart was fresh out of Ts.

          • There once was a poem so awful
            the courts all declared it unlawful.
            One judge decamped,
            Exclaiming, verklempt,
            “I must comfort myself with falafel!”

            I…I think we’re done here. Can we be done here? I am done here. Back to learning how to use adjacency operators in literature searches, which occupation I shall conveniently blame for the quality of my poetry. Next search: verklempt adj10 falafel. Oh wow, now _there_’s the title of a truly awful poem.

  19. I’m pretty bad at most board games but I have this Scrabble rivalry with a family friend that dates back to…sometime in middle school, and we’re about evenly matched at this point. Looking forward to soundly kicking his butt when I go home for Thanksgiving!

  20. Heather, I studied Monopoly probabilities too! Those reds and oranges are such prizes. Illinois + that Chance card = A BLESSING.

    My nephew is the unbeatable Monopoly-player in my family – we always used to have fierce Monopoly battles that devolved into bitter arguments, but they were so much fun. We played by house rules to keep things interesting, and I ended up writing an entire rule booklet in legalese that we would scream-quote at each other to prove our points. My nephew and I aren’t on speaking terms anymore, and SHOCKINGLY, it isn’t because of Monopoly.

  21. I want Bananagrams!! It looks so cute and words are great!
    Else I hardly ever play boardgames, as I had to when I was a child, forced “family time” to pretend we were a happy family – of course it rarely was fun, but the worst was, *I* had to tidy up afterwards, even though I never even wanted to play in the first place..

  22. games seem to fall into two categories for me: i’m quite good at them and can win or hold my own against anyone (set, trivial pursuit, taboo)
    OR i am so terrible at them that there are specific house rules barring me from playing certain roles and i serve as an example of what not to do whenever this game is taught to new people (betrayal at house on the hill: i am not allowed to play the ghost)


    (And Scrabble but I always feel nervous saying that because I know there are people out there who could beat me)


  24. Board games are one of those things that sharpen the dysfunctional details of my family. Sorta way people coo over the idea of what they ID as a pretty girl having all brothers, how protected and cherished I must of been. But with board games the dissonance doesn’t leave me feeling like a ragged wound just befuddled and wondering what I missed out and if I should feel sad or something.

    The befuddlement is how anyone got the chance to play through a board game enough to like it and develop skills at it in childhood with siblings. That it didn’t get banned or taken away because of fighting or destroyed by fighting.
    Like I cannot picture that at all, but I can picture picking up board games as an adult cause of not getting to play them and finally have agreeable persons with which to play them.

    I think I’d be a whiz at Trivial Pursuit because I’m a random “useless” facts sponge.

  25. Dixit is such a horrible game!! For me, anyways. When I lose at other games (which, I’m a sore loser in general, so we’ve got quite a collection of cooperative games by now and there are some games that I never play – spinoff post: What are the board games you purposely never play, and why?) – anyway: when I lose at other games, it will mostly hurt my intellectual vanity, so no actual harm done, I’ll get over it. Losing at Dixit, as someone who’s not neurotypical, was the most isolating experience. NO ONE saw things the way I saw them, ever. I lost so badly, and afterwards felt terrible and empty and like no one would ever understand me, and I would never understand anyone else.
    So, yeah … I’m pretty ok at Backgammon? On a rather intuitive basis, also, long story involved, but anyway, I like it. My Iranian friend laughed in my face when I tried describing the game because she didn’t know it by that name, but I was pretty sure she’d know it under a different name, probably the original one, and of course! “backgammon” turned out to be a completely ridiculous name for it, and we had a lot of fun playing afterwards.

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