This site contains affiliate links to products. We may receive a commission for purchases made through these links. Learn more

30 pieces of dating advice from films

30 pieces of dating advice from films

30 pieces of dating advice from films

If you asked us for our best piece of dating advice it would be to stop doing that weird thing with your eye. Which, as helpful as it is, also shows that we need a bit of help with our wingman repertoire.

So we scoured the history of cinema for some of Hollywood's advice on how to deal with the potentially hellish world of dates.

(Images: All Star, Rex Features)

Cal (The 40-Year-Old Virgin)

Year: 2005

Played by: Seth Rogen

"Just ask a question, that's it. Because women do not care about what you have to say at all and all they want to do is talk about themselves"


Florence (Greenberg)

Year: 2010

Played by: Greta Gerwig

"Hurt people hurt people"


Sala (The Rum Diary)

Year: 2011

Played by: Michael Rispoli

"Do not confuse love with lust nor drunkenness for judgment."


Will (Robin Hood)

Year: 2010

Played by: Scott Grimes

"The secret to success is to never go for the prettiest one."


Wallace (Scott Pilgrim Vs The World)

Year: 2010

Played by: Kieran Culkin

"If you want something bad, you have to fight for it. Step up your game...break out the L-word."


Trent (Swingers)

Year: 1996

Played by: Vince Vaughn

"If you call too soon you might scare off a nice baby who's ready to party."


Juan (Vicky Cristina Barcelona)

Year: 2008

Played by: Javier Bardem

“Only unfulfilled love can be romantic.”


Prime Minister (Love Actually)

Year: 2003

Played by: Hugh Grant

"I'm not sure that politics and dating really go together."


Lillian (Bridesmaids)

Year: 2011

Played by: Maya Rudolph

"Make room for someone who is nice to you."


Paul (Midnight In Paris)

Year: 2011

Played by: Michael Sheen

"Sex and alcohol – it fuels the desire but kills the performance."


Oz (American Pie)

Year: 1999

Played by: Chris Klein

"You ask them questions, and listen to what they have to say and shit."


Tommy (Friends With Benefits)

Year: 2011

Played by: Woody Harrelson

“It’s not who you want to spend Friday night with. It’s who you want to spend all day Saturday with.”


Sean (Good Will Hunting)

Year: 1998

Played by: Robin Williams

"You're not perfect, sport, and let me save you the suspense: this girl you've met, she's not perfect either. But the question is whether or not you're perfect for each other."


Alex Hitchens (Hitch)

Year: 2005

Played by: Will Smith

"A woman who doesn't want to kiss takes her keys out, puts them in the door, goes in the house. A woman that wants to kiss, she fiddles."


Gary (The Break-Up)

Year: 2006

Played by: Vince Vaughn

"It's not about doing the things you love, it's about doing things with the one you love!"


Alvy Singer (Annie Hall)

Year: 1977

Played by: Woody Allen

"A relationship, I think, is like a shark. You know? It has to constantly move forward or it dies."


Rachel ((500) Days Of Summer)

Year: 2009

Played by: Chloe Grace Moretz

"Just because she likes the same bizzaro crap you do doesn't mean she's your soul mate."


Harry (When Harry Met Sally)

Year: 1989

Played by: Billy Crystal

"No man can be friends with a woman that he finds attractive. He always wants to have sex with her."


Yuri (Lord of War)

Year: 2005

Played by: Nicolas Cage

"That’s the trouble with falling in love with a dream girl. They have a habit of becoming real."


Van Wilder (Van Wilder)

Year: 2002

Played by: Ryan Reynolds

"First dates are interviews"


Joel (Eternal Sunshine...)

Year: 2004

Played by: Jim Carrey

"Constantly talking isn't necessarily communicating.."


Kate (Drinking Buddies)

Year: 2013

Played by: Olivia Wilde

"That's the problem with heartbreak, to you it's like an atomic bomb and to the world it's just really cliche, because in the end we all have the same experience."


John (Wedding Crashers)

Year: 2005

Played by: Owen Wilson

"Love doesn't exist, that's what I'm trying to tell you guys. And I'm not picking on love, 'cause I don't think friendship exists either."


Laramie (The Arizona Raiders)

Year: 1936

Played by: Buster Crabbe

"Romance is when a man runs after a woman until she catches him."


Barney (The Expendables)

Year: 2010

Played by: Sylvester Stallone

"The man who best gets along with women is the man who can get along without them."


William (Finding Forrester)

Year: 2000

Played by: Sean Connery

"The key to a woman's heart is an unexpected gift at an unexpected time."


Officer Michaels (Superbad)

Year: 2007

Played by: Seth Rogen

"You don't want to meet a chick in a bar man...you gotta go to other places. You gotta go to spin class, a farmer's market...just somewhere social, non-threatening"


Louis 'Mountain' Rivera (Requiem For A Heavyweight)

Year: 1962

Played by: Anthony Quinn

“When you’re out with a lady, you should act special.”


Amy (Her)

Year: 2013

Played by: Amy Adams

"I think anybody who falls in love is a freak. It's a crazy thing to do. It's kind of like a form of socially acceptable insanity."


Mac (The Heartbreak Kid)

Year: 2007

Played by: Rob Corddry

"Plaster on a fake smile, plow through the next half century, sit back, relax, and wait for the sweet embrace of death!"