The early stages of dating someone new is quite frankly the most uncomfortable and awkward at the best of times but when you add your friends into the mix for a double date it is most certainly a recipe for disaster. So to celebrate the release of Kevin Hart’s About Last Night on DVD and Digital, we have compiled a list of the most awkward double dates in film.

This hilarious romantic comedy (which is a modern reimaging of the 1986 movie of the same name starring Rob Lowe and Demi Moore), See’s Bernie (Hart) and Joan (Regina Hall) involve themselves with a passionate hook up. They decide to bring their friends along for a double date, but while Bernie and Joan get increasingly drunk and incredible “hands on” with each other (to the point where they actually quite brazenly sneak off to the toilet for sex) Danny (Michael Ealy) and Debbie (Joy Bryant) are left to watch this car crash date. Thankfully for them, without the help of their embarrassing friends, Sparks soon set to fly between the pair.


“When Harry Met Sally” chronicles the age old question of can men and women really just be friends, over a period of 11 years.
Awkward Double Date Moment: Harry (Billy Crystal) and Sally (Meg Ryan) are said friends so when Sally sets up Harry with Marie and Harry sets up Sally with Jess. The dates go horribly wrong; neither date takes much interest in Harry or Sally; in fact they couldn’t be more bored. Instead we see Marie and Jess hit it off, and end up getting married.


Hitch is THE “Date Doctor” for hopeless men. Whilst taking men who are not so confident when it comes getting woman under his wing falls madly in love himself, but is not as successful as his clients.
Awkward Double Date Moment: Hitch (Smith) has a double date with Sarah (Mendes) and her boss and his wife at a cooking class. Unfortunate for Hitch he has food allergies. In the midst of trying to impress not only Sarah but the whole group his whole face starts to hilariously balloon.


Who doesn’t know and love Goodfellas? This gangster film is based on the highs and lows in the mobster life of Henry Hill, gangster turned grass and all round smuck!
Awkward Double Date Moment: Henry (Liotta) reluctantly agrees to be Tommy’s (Pesci) wingman because he wants to “bang some broad” Karen (Bracco) is the “broads” best friend and Henry’s date, but Henry pays her no attention and can’t wait to get out of there for a meeting. A 2nd date is arranged but Henry fails to turn up, leaving Karen in tears at the restaurant in front of Tommy and his date. Karen tracks him down and gives him a verbal bashing in front of all his gangster friends making one hell of a scene.


John Bennett (Wahlberg) had a childhood wish, that his beloved Ted was alive. His wish came true and Ted has been at his side ever since. Their typical “man” friendship is tested when John’s girlfriend Lori (Kunis) wants to get more serious.
Awkward Double Date Moment: Lori innocently tries to make conversation with Ted’s new girlfriend by saying “I’m always fascinated by Ted’s girlfriends” The reaction from Tammy Lyn is one of ditzy bimbo to psychooooo with an onslaught of verbal abuse, leaving Lori stunned into awkwardness.


Peter (Jason Segel) is suffering from a broken heart after a break up with his girlfriend Sarah (Kristen Bell). The order of the day, a trip to Hawaii to forget all about it. Unfortunately for Peter, Sarah is at the same resort, with her new boyfriend.
Awkward Double Date Moment: Sitting down to dinner, Peter, Sarah, her new boyfriend and Rachel (Kunis) Peter’s “love interest” from the resort are discussing Sarah’s film. The boys totally rip the film to shreds leaving Rachel awkwardly trying to defend Sarah’s choice leading to that oh so awkward silence.