It's the winning that counts: experts reveal how to ace the annual Christmas board game showdown

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Stylist reveals the strategies to help you emerge victorious from the annual Christmas games showdown

Words: Nell Frizzell

Until you’ve screamed “I hate you and everything you’ve created!” into the face of your blood relative over a cranberry sauce-stained pile of paper money, you simply haven’t ‘done’ Christmas. Forget carols, forget presents, forget turkey, forget snow, forget paper hats, forget tinsel, forget Santa, and you can most definitely forget goodwill to all men, because what Christmas is really about – what it really means – is falling out with your loved ones in a semi-drunken haze playing board games.

You may have guessed by now: I love games. Simply adore them. From Balderdash to charades, Pictionary to Kerplunk, I am rarely happier than when whizzing along, astride a winning streak. But I’m horrible when playing them. I gloat, I groan, I gnash my teeth. I hide Monopoly money under my seat and take great relish in laying a word like ‘quartz’ across a triple word score. I sweat, I swear, I storm about the room when losing and can be insufferably smug when winning. When my family refuse to play Scrabble, I’ll simply commandeer their rack of letters and play against myself. I am, in short, a monster. But – and I insist on your agreement with this – when it comes to playing games at Christmas, we all are. That is what the dark underbelly of Christmas is about, after all: family disharmony, hurt feelings, unbearable competition and a thundering anticlimax.

I heard a story recently about a particularly exasperated (not to mention heroic) father who, after a knuckle-chewingly disastrous game of some vicious festive diversion, picked up the board – the whole board – walked calmly to the fire, muttered, “Well, that was fun” and then threw the entire thing into the licking flames. Somebody put that man on the Christmas honours list. He is, for me, the very spirit of competitive Christmas.

If, like me, you’re determined to conquer all on the 25th no matter how lacking you are in natural board game talent, you’ll be pleased to know that proven strategies exist to win at most games. It may involve tactics, preparation, a little light reading and some all-out cheating but you can win. Stylist asked the experts for their tips on how to claim victory at some of the most prolific festive games...


How many times have I stared down at someone’s frantically scribbled line-drawing of a bucket with two bananas for handles and thought, “Why? Why is my own mother trying to undo me yet again? Why can nobody on this earth just draw?” On paper, the timed game during which a nominated person must sketch a clue from a card without resorting to words, numbers or speaking, while their teammates try to guess the word or phrase sounds easy. It is, in fact, infuriating.

  • Keep it simple. BuzzFeed illustrator and Pictionary whizz, Becky Barnicoat, argues that the secret is to spend more time thinking and less time sketching. “Don’t just start madly drawing or you’ll end up with a weird scribbly cloud with a leg and two arrows pointing to something unintelligible,” she warns. “Take a moment to think of the simplest way to draw the clue then calmly illustrate it.”
  • Agree on some visual hints beforehand. This isn’t cheating. Well, not really. Up your chance of winning by cajoling your teammates into agreeing on some illustrative shorthand, such as a musical note for a song title, a box with antennae for a TV show, two dashes for a compound word (like left-handed or big-boned), an ear for ‘sounds like’ clues or a daffodil for a rhyme – anything to give you the advantage.
  • Homonyms (words that are spelt or pronounced the same but mean different things) are your friend. Can’t draw ‘handmade’? Draw a hand and then a maid’s uniform. Can’t draw ‘springtime’? Draw a coil and a watch instead.


When better to revel in an unfair housing market, impractical infrastructure, greed, chance and the thirst for power than over a family game of Monopoly? Dr Hannah Fry, a lecturer in the mathematics of cities at the Centre for Advanced Spatial Analysis at UCL, has written the perfect book for such an occasion. In The Indisputable Existence Of Santa Claus, she not only mathematically calculates the ideal ratio of present price to pleasure in giving, she also explains how to win at Monopoly. The secret, she says, is dependent on the number of opponents and how closely you follow the official rules.

  • Buy up the properties closest after jail. According to Dr Fry’s calculations, jail is the most-visited square on the board and so the streets that immediately follow are likely to get landed on far more than, say, Mayfair.
  • Speaking of Mayfair: stay away. “There are people who always go for Mayfair but it’s a fool’s errand,” says Fry. Even though it’s the best one on the board as a stand-alone property, it’s expensive to buy and one of only two properties (with Park Lane) so there’s a lot less chance of someone landing on it than, say, one of the orange streets.
  • Utilities are pointless. As someone who hungrily buys up the train stations like a Pumpkin Café, I was surprised to hear this. But, apparently, train stations, the Electricity Company and Water Board will never bring much of a return on your investment by dint of you not being able to build on them.
  • Buy orange and light blue streets, particularly if you’re playing against only one opponent. Thanks to the jail effect, orange will always be frequently visited and you don’t need a lot of capital to snap them up early.
  • Read the rules. According to Fry, hardly anyone plays by the actual rules of Monopoly. “One of the official rules is that if you land on a property, as well as having the opportunity to buy it, you can also put it to auction for all players, including yourself.” So you can land on Fleet Street for £220 but win it for £80 at auction. “If you play by the proper rules,” says Fry, “the game shouldn’t go on for ages.” Praise be to that.


I spent some of my happiest Christmas moments sitting at the huge oak table of an octogenarian German refugee, watching her smoke, drink damson gin and wipe the floor with her family at Scrabble. Sadly, she is no longer available for tips but I called World Scrabble Champion 2016 and Mindsports Academy Scrabble Ambassador Brett Smitheram, to pick his brains about how to win at this tricky pursuit.

  • Swot up on handy two-letter words that fall within the rules. “It’s a word game so, inevitably, you have to know some words – those are your tools,” says Smitheram. And of all the tools, two-letter words can be incredibly valuable when it comes to sneaking in some extra points. Read and learn: qi, za, xu, wo, ef, ka and om.”
  • Plan ahead. “Don’t just think about what you can score now,” advises Smitheram. “See what opportunities you can open up to score in your next move.
  • Remember – it’s about points, not words. To win, you sometimes have to play an incredibly unglamorous word in the right way, rather than revel in a multi-syllable extravaganza. As Smitheram puts it, sometimes you have to play ‘dog’ instead of ‘quixotic’ if you really want to win.
  • Get those triple word scores. Not least because if you manage to hit two triple word tiles with one seven-letter word, your score will be multiplied by nine.
  • Lastly, play your own letters. “When you start worrying what your opponent’s going to do, you screw up your own letters very quickly,” says Smitheram. You can tie yourself up in knots worrying that someone else is going to capitalise on available triple letter or double word tiles. But there’s no way of knowing what your opponents have on their rack and the more opportunities there are on the board, the more likely you are to profit from them.

Photography: Pixeleyes