The Matchmaker selects a character from their hand. The other players then select the character they feel is the best match from their own hands. The matchmaker chooses the best match, and the player that supplied the match receives the points listed on the pair of winning cards.
There are two gameplay options.
One is simply as described above. Cards are played face down, and the best pairing is selected by the Matchmaker. Very similar to Apples to Apples and Cards Against Humanity.
The Second, which I highly recommend, is to play each card face up, and create a narrative for why the pairing makes sense. This sounds intimidating, but doesn't have to as in depth as the rules suggest (i.e. describing a first date).
One thing to note is that, similar Cards Against Humanity, when you score, you receive the pairing you helped create. This means these cards are out of play for the remainder of the game. This can be rough in a long game, or a large game (we played with 10 players).
There is also a mechanic for challenging the Matchmaker's ruling. We did not find this necessary in our game, but it seems like a good balance to favoritism and inside jokes.
Another rule worth pointing out, if you don't know the character on your card, you may discard it and draw another. This really kept things going smoothly as no one needed to whisper to their neighbor for help, or look up the information on their phones.
I'm adding this section, because I feel the box is a bit lacking. It is very compact, and once the cards are unwrapped there isn't any really organization. Just four stacks of cards plopped in the box. We added one set of the blanks, and were worried it might not close. It did, but I can't imagine adding many more blanks, or a future expansion into this box.
The cards themselves feel nice, and shuffle pretty well. I wouldn't say they need to be sleeved.
Pop culture fans
party game fans
Our group really enjoyed this game. One person even uttered the words "Better than Cards Against Humanity." We all agreed that the creative component made this a little more interesting and challenging.
In a climate of increasing Apples to Apples and Cards Against Humanity clones, and shallow party/large group games in general, this game was a pleasant surprise. It will definitely remain in rotation for lighter game nights and cons.