Top 10 Romantic Comedy Drinking Games

The 40 Year Old Virgin

Drink Every Time:
  • Andy says or does something nerdy/dorky
  • Andy screams
  • Andy doesn't feel comfortable doing something
  • Andy gets on a bicycle or mentions it
  • Andy misses out on a chance to have sex
  • Nipple (drink for each one) 
  • Someone says "gay", "virgin", "sex" aloud
  • Intercourse with an animal or object is mentioned

Finish your Drink:
  • Someone vomits their daiquiri
  • Andy breaks out into a singing and dancing montage 

50 First Dates

Drink every time:
  • There's a new day
  • Whenever you see a "Happy Madison" regular
  • Drew Barrymore cries
  • When you hear "Wouldn't it be Nice"
  • When Drew Barrymore forgets something
  • When Rob Schneider does something stupid
  • Whenever you would have thrown in the towel 

Finish your drink:
  • When Adam Sandler's video diary saves the relationship 

500 Days of Summer

Drink Every Time:
  • A new Day number appears on screen
  • Summer is wearing or holding the color blue
  • Tom writes a new greeting card
  • A season is mentioned (Winter, Autumn, Spring, and yes, Summer)
  • "Penis" or "Bitch" is said aloud
  • Rachel says something very wise

Finish your Drink:
  • Tom breaks out into a song and dance number
  • Summer is wearing an engagement ring

Along Came Polly

Drink Every Time:
  • Reuben has a bad date
  • For every button that is undone on Reuben's shirt
  • A scene is in the bathroom
  • Characters are dancing
  • The ferret is on screen
  • "Polly" or "Reuben" is said aloud

Finish your Drink:
  • Someone "sharted" themselves
  • Along comes Lisa

Crazy Stupid Love

Drink every time:
  • They go to a bar
  • Jacob (Ryan Gosling) picks up a girl
  • Cal (Steve Carell) messes up a situation that was going well 
  • The words "Divorce" or "David Lindhagen" is said
  • Jacob offers dating advice
  • Someone drinks on screen
  • Someone cries
  • Hannah (Emma Stone) is upset 

Finish your drink:
  • Jacob meets Hannah 
  • A backyard brawl breaks out

Forgetting Sarah Marshall

Drink every time:
  • There is male nudity
  • Someone eats or drinks
  • Peter (Jason Segel) cries
  • Peter plays the piano
  • Sarah Marshal is on television
  • Kunu gives advice
  • The word's "Sarah" or "Marshal" are said
  • A wide shot of Hawaiian landscape is shown 
  • There is a vampire reference (voice included)

Finish your drink:
  • Peter takes the photo 
  • Peter performs his musical 

Pretty Woman

Drink every time:
  • Vivian is barefoot
  • Edward does something romantic for Vivian
  • Vivian has a hard time adjusting or does not fit into the wealthy elite lifestyle
  • Money is exchanged
  • Vivian applies makeup
  • Vivian changes clothes
  • Edward doesn't take advantage of his many luxuries due to a limitation (personal or psychological)
  • Edward acts like a sympathetic bigot, he means well but comes off as pretentious

Finish your drink:
  • Someone finds out who Vivian really is
  • And they lived happily ever after

The Princess Bride

Drink every time:
  • "True Love" "As you wish" "Inconceivable" or "Wing (Ring)" are said
  • Inigo informs someone of his fathers fate
  • Westley can't control his limbs in a comical fashion
  • Someone dies
  • Fred Savage is shown
  • Fezzik's (Andre the Giant) size is referenced 

Start a waterfall:
  • A sword fight breaks out

Finish your drink:
  • The grandfather finishes reading the story 

When Harry Met Sally

Drink every time:
  • Someone’s relationship status is mentioned or changes 
  • An interview segment is shown 
  • The trip to New York is referenced 
  • Sex is referenced 
  • Harry or Sally’s former spouses are mentioned
  • Someone is on the phone

Take 5 drinks every time:
  • Time jumps forward five years

Finish your drink:
  • Every time Harry “Meets” Sally 
  • When you’ll have what she’s having 

You've Got Mail

Drink every time:
  • The word "Fox" is said or spelled aloud
  • Kathleen Kelly's name is said in full
  • "Around the Corner" "You've Got Mail" or "Brinkley" is said
  • A typewriter of Frank's is shown
  • Dave Chappelle's character (Kevin) acts as the quirky black friend
  • A different generation of "Fox" is shown on screen or referenced other than Joe
  • There is a voice-over
  • Joe or Kathleen's AOL screen name is said aloud (Shopgirl or NY152)
  • Joe Fox says uses an analogy that's clever or insightful
  • Kathleen Kelly uses an analogy that cute 

Finish your drink:
  • When Joe Fox and Kathleen Kelly meet online for the first time
  • When she wanted it to be him... She wanted it to be him so badly