Movie Dates: The Good, The Bad, and the Awkward

Sadly Valentines and February came upon me so fast this year, I didn't have time to make a bunch of romance movie themed lists like I usually do. But still, I felt I owed you one.. and this one was inspired by my recent viewing of Begin Again that led me to ponder GREAT dates in film.. And then I pondered the flip side. As a result of my ponderings, I present to you, the 5 WORST DATES IN FILM. Countered with the 5 BEST. Meanwhile, I'll add a little of my own dating history and let you know which of these I've had similar experiences with. Also, if you're craving more lists, check my archives in the months of February the last few years. Or you can just read my favorite list I've done HERE. Now onto this year's list.



In Fever Pitch, Drew Barrymore's character gets an awful case of food poisoning Have I ever thrown up on a date before? The answer is yes. It was at an amusement park after a spinning ride. Thankfully the vomiting did not occur in FRONT of my date, as I made it to a bathroom before it happened...but it was still pretty embarrassing. But that was nothing like the date below in Fever Pitch! Drew Barrymore sure has been on some bad cinematic dates. I considered putting her blind date with Adam Sandler from Blended, but as Fever Pitch is a better movie we'll let this one edge it out (though if I had a choice on which date to live through I'd probably rather not ever want to experience the Hooters date in Blended. Shudder.)


In When Harry Met Sally, the two titular friends think that they should set each other up with their respective besties. What results is a pretty crappy double date when those besties have no interest in who they were set up with (Harry and Sally,) and instead fancy each other. Have I been on a double date where my date is way more interested in another girl? At least twice. Did I have a prospective Harry in the wings? Nope because on one of them the date for my friend was my brother. So basically this shameless idiot  I went out with was flirting with my brother's date in front of him and was neglecting me at the same time. Definitely one of my worst dates I've been on. 


In Bridesmaids, Kristen Wiig's character Annie gets set up on a blind date with a recently single father who doesn't really seem ready to be dating again. While she's waiting for him to get ready, he leaves her with his son forcing them to make perhaps the most awkward small talk ever. Then she gets to overhear what her date REALLY thinks of her. Though I have been forced with my fair share of awkward small talk, luckily the second part has never happened to me... at least on a date!


Hitch's track record with Sara Milas is pretty bad. On their first date, he kicked her in the head and reminded her of a horrible family secret. During their second, he gets really bad food allergies and later gets mildly drunk off of allergy medicine. Thankfully I have NOT had any allergic reactions to food during dates... unless you count my tongue's abhorrence for onions. One time I was out with an English gentleman, and in the middle of a bite I discovered a very disgusting crunch in the form of an onion... and well I forgot my manners by fishing it out of my mouth. Oops. That date was actually going pretty well prior to that, so I think my "allergy" killed that one dead. 


Sadly there's not any clips of this date on youtube, but it's basically the quintessential horrible date that I find myself experiencing often. The type where you can tell you've got nothing going on almost from the get-go but you just have to find a way to make conversation anyway. Plus it's got Janeane Garofalo who plays Randy Quaid's moody date that jumps down his throat to everything he says. Have I been this person? Perhaps shades of her in some ways. Have I gone out with a guy like her that just can't help but make every interaction as awkward as can be? Yep. One of my favorites of recent memory was a guy who when the waitress made a comment about "your boyfriend is so nice to take you out!" kept saying the whole date long "that was SO awkward that waitress said that." Not as awkward as you constantly bringing it up buddy. 


I don't think ANYONE could ever have gone on a date like this, and thankfully I sure haven't! In About A Boy Hugh Grant's Will takes out a woman who has an unexpected visitor tagging along her neighbor's weird pre-pubescent son named Marcus. Marcus makes EVERYTHING more awkward.. and it doesn't help when he accidentally kills a duck with a loaf of bread. Oops. But to make matters as worse as they can be, when they drop off Marcus they discover that his mother just attempted suicide. Can't get much worse than that!

Honorable mentions: Back to the Future (going on a date with your mom is never ideal for a son,) Pulp Fiction (passing out on and needing life-saving assistance is a little embarrassing,) Blind Date (I blocked this movie from my subconscious, but I remember the whole movie revolved around onnnnne horrible date.) Silver Linings Playbook (their date or non-date at the diner is just really awkward) The Graduate (Ben Braddock is just awful to his date who happens to be the daughter of a woman he's been sleeping with.)



It's a toss-up here between Joel and Clementine's date at the frozen pond where they have a really precious moment lying on the frozen ice... OR their date parked near a Drive-In movie where they make up their own dialogue since they didn't pay to get in. As a movie lover, I think the second option would be incredibly fun. And will have to put that one on my to do list. 

This one is over fairly quickly and if you haven't seen the movie the rest might not make a lot of sense!

#4. (500) DAYS OF SUMMER

Again this whole movie is rife with dating ideas to plunder from. The one I think many people associate this movie with is the classic "play house at Ikea date," but it's not my favorite. The most romantic would have to be hands down taking her on a tour of his favorite architectural spots in LA and then to his favorite spot in the city to admire the view. Oh and then completing the day with an arm tattoo of his vision for the city. I guess I actually have done this date.. but with friends! A couple years back when I was in Los Angeles I made it a point to see some of Tom Hansen's favorite spots in the city and it was lovely.


In About Time, Domnhall Gleeson's Tim and Rachel McAdams' Mary meet and basically have their first date in a very unique restaurant: a restaurant where all the lights are turned off and you sit completely in the dark! They hit it off and talk for hours without knowing what the other person looks like... just simply enjoying each other's company. This particular date is incredibly romantic in film but would be pretty tough to recreate successfully in real life. You'd have to take quite the gamble in going on a date with a stranger in this way that you would be able to A) have anything in common with them at all and B) actually find them attractive afterward. 

I just felt like my Korean readers needed subtitles on this, so I found a video specifically for them.


Mark Ruffalo's Dan tells Keira Knightley's Gretta all about his first date with his ex-wife, and then... well decides to recreate it for her (in a platonic way?) History aside, you can't fault the guy for using this move because it's a pretty good one. The date? Taking their ipods and swapping songs as they walk all over New York City and admire the sights set to their own soundtrack. This date only works if you have got the same taste in music as the person you're with though. It might kill the mood to ask them to skip to the next song if they're having a moment with it. Might be best to decide on a playlist before you go to avoid any awkwardness.


Jesse and Celine meet on a train and hit it off. Not wanting to end their conversation, he convinces her to spend the night with him exploring Vienna before his flight the next morning. Celine agrees and they spend the next two hours deep in conversation all while discovering a beautiful European city. The lesson here? Europe trumps all. Basically yeah if you want to have an unforgettable date stay up all night walking around a beautiful city having an amazing conversation. That's all it takes.

Honorable mentions: 10 Things I Hate About You (paddle boat & paintballing) Notting Hill (secret garden) The Fault in Our Stars (Amsterdam picnic and really... everything in Amsterdam.)


Sarah said...

The movie "Hitch" just drives me crazy! For the most part, I was just stressed out! Not romantic (for me, at least) at all!

Fun list. I had my fair share of weird and awkward dates too.

One that was funny was we went to a Chinese restaurant, we all ate family style and when I went to get some more shrimp, my date thought I was trying to take food off of his plate (not the plate right next to him that had shrimp on it) and then he spent the rest of the meal being very protective of his food. Afterward, the group decided it would be fun to make cookies...but no one but me knew how to make them. We went to the grocery store where they literally were like, "What ingredients do we even get to make chocolate chip cookies?" I ended up picking up a bag of chocolate chips, picking up all of the ingredients based on the recipe on the back of the bag, and then making the cookie dough and eventually baking the cookies while everyone else watched a football game. That sure was fun.

Johanna said...

I've block out most of my dates.

I do remember one where my date picked up a couple of bottles of bubbles and we spent the evening talking and watching and blowing bubbles. It was amazing the conversation that flowed. Sweet date.

No, I'm not going to say who it was.