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Not a board game, but I'd highly recommend Dominion. It's quick, easy and addictive. We used to play a lot of Settlers or Ticket to Ride before Dominion came along, now, it's been pretty much exclusively Dominion for the last several months.
As mentioned below, Dominion is great.
For a quick, really fun filler I'd recommend Tsuro. Can be very light or pretty deep, but takes 5 minutes to setup and 15 to play. Can play up to 8, I think, and is great for kids. We have fun with it all the time.
I've been totally hooked on Dominion recently too. It's actually become kind of an obsession collecting the various expansions (there are eight expansions plus the base game). The game is definitely better with the some of the expansions, but I played the base game for a long time with no complaints.
What's a good play set for 2 players? I love the game but we find that it is very one sided as things go on when we use the card sets they recommend to start with.
If you like "Apples to Apples" and matching cuddly with Boy Scouts...you HAVE to play "Cards Against Humanity".
In a two hour game of Cards my friend and her mom learned more about each other then they have ever done so with "real talk". It's a great fun game especially for casual audiences that are new to it. If you like it try the expansions.
My son thought he was getting rid of a card just to get rid of it and on "Twisted", he played "Rosa parks"
That's too bad the first run didn't go better. I know the rules can seem confusing at first, but it really is a pretty simple game once you start playing. I hope it gets better for you.
I don't use the recommended card set ups. Those can be good at first when you are learning the game, but once you've played it once or twice it's better to use the randomizer cards and just have 10 random card piles. If you're playing with just the base game, you might consider adding one of the expansions. I'd go with Seaside or Intrigue at first.
One of my coworkers uses Cards Against Humanity as a social filter. If a person doesn't like playing Cards Against Humanity, he's not interested in being social with that person.
What he said.
Pandemic rules. Also, though it is competitive, have a look at Galaxy Trucker. You build ships and then watch them get blown to bits. Loads of fun, and the randomness of the second half of the game makes it not so cutthroat. Lots of fun!
Never laughed so hard in my life. Gave this to some friends and we played it tonight.
My buddy got me Cards and the expansion pack
and I played it with a good mix of liberal and conservative people. One half of the group was laughing their butts off, the other half was looking up definitions of raunchy terms on their phones. Lots of fun.
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One that was a hit for us was to get pictionary, but then buy a huge dry erase board and draw a line down the center. Two teams. Basically creating a win lose or draw type game. Very loud / high energy.
I love Dominion but the replay-ability for me grew tires since the "big money" approach nearly always is optimal. There is an iOS version of the game that is very good as well.
I think he'd be fine... especially given the game is Co-Operative. At no point will he be "on an island" with regards to having to make his own decisions. Everyone works together discussing the joint strategy for every move. The initial adoption of the rules is admittedly a significant hurdle, but once you have that "aha" movement and "get" the mechanics, it's actually a rather simple game to play. Not so simple to master.
Some of us like to
and some of us like to 
Wits 'n' Wagers is a good party game for big groups. Others would be Pictionary, as mentioned, or Taboo/Catchphrase.
Absolutely...plus, it's open handed and communal. You can guide anyone of pretty much any age.
My MIL negates this rec
Usually on the game page of whatever game it is, on boardgamegeek.com, they have player aids and such to help folks learn the various games.
You just need to play through it once or twice. It's not complicated at all. My 8 year old can play this game. And it's a fantastic game.
Hmm, I've played tons of Settlers, Carcassonne, other strategy games, but just couldn't get into Dominion. The difference might be my girlfriend as well, as she hasn't played any strategy games, and was like
.
I've only played the Prosperity expansion but I'm sure the mechanics are very similar across the board.
Woa...I like the look of that. I'm almost finishing up making a Crokinole board...I think I'll knock out that Quarto game real quick in my garage, just after...
