Movies To Watch When You're Sad About Being Single

Love Actually

Just the best ending to any work party ever, no big deal.

Might as well get it out of the way first.

There are so many cute moments. Colin Firth and the Portuguese woman learning each others’ language, Hugh Grant dancing alone to the Pointer Sisters, Laura Linney finally getting to make out with that sexy accented guy (just ignore how that storyline ends), the American girls freaking out over the British guy’s accent.

Also: the scene where Emma Thompson realizes her husband is probably definitely having an actual affair, so she goes off alone to cry for just a minute, and there is that really, really sad Joni Mitchell song playing, and oh god it’s so painful. I always end up crying a little too, which provides a nice catharsis for whatever stupid dude situation I happen to be upset about that month.

Less Than Zero

I watch this movie when I want to fantasize that I’m a rich young L.A. model during the 80s, making out with young Andrew McCarthy in avant garde architectural spaces while catchy Bangles songs play. This happens once a week or so.

Auntie Mame

I MEANNNNN JUST LOOK AT HOW COOL SHE IS. Auntie Mame’s a classic movie, and it’s incredible. Mame is a middle-aged, single, fabulously wealthy, cosmopolitan, fun-loving, liberal New Yorker who inherits her young nephew, whom she’s never met, after her brother dies suddenly. The movie is long, because it was made back when the average human’s attention span was longer than the average goldfish’s, and chronicles their lives together up until the boy is grown and Mame is elderly (but still fabulous!).

I love that Mame is portrayed as a vital, intelligent, cultured woman who’s just Living Her Life. She never expresses regret at not spending a long time with any one man, and none of the other characters ever imply she’s missed out on anything, or has failed in any way.

I can’t think of one contemporary movie with a similar message and/or character, which is a pretty shitty state of affairs.

Bridget Jones’s Diary

Netflix should just create a genre called “Colin Firth movies in which he spends a lot of time being all unreadable and Colin Firthy but in the end it turns out he is filled with smoldering passion and also is an excellent kisser.” I feel very strongly that this genre would generate a lot of traffic for them.

Wedding Crashers

It’s a romantic comedy that’s actually funny! There’s Vince Vaughn and Owen Wilson’s great brolationship. The gay artist brother hissing, “I made you a painting!” while lying on top of Vince Vaughn. Isla Fisher jumping and climbing onto Vince Vaughn countless times like he’s a big ole tree. Vince Vaughn flatly stating, “The painting was a gift, Todd. I’m taking it with me.” Obviously I’m just in love with Vince Vaughn. Moving on.

I Hate Valentine’s Day

Nia Vardalos wears some pretty cute tops in this movie.

This movie isn’t “good,” but it is somehow pleasurable to watch. I can back this up with a fun fact: I read Roger Ebert’s review of it, and he only gave it 1.5 out of 4 stars, but the viewers gave it the full. So I Hate Valentine’s Day is sort of like the Lenny Kravitz of movies.

My favorite aspect of it is the long stretch where the couple has broken up due to Miscommunications and Unspoken True Feelings. They’re both totally in love with each other, though, and eventually it’s the woman who starts reaching out and trying to get him back, and he doesn’t respond in an encouraging way but she just keeps on trying.

It strikes me that this dynamic is rare in pop culture; society is much more comfortable with men being the ones to take chances and risk rejection (such as in Wedding Crashers). So watching a movie with the opposite dynamic really comforts me when I think about the times I was cringeworthingly idiotic in my own personal life.

The Terminator

Tell me again how to construct one of those dynamite sticks, Kyle.

Sometimes you’re in the kind of mood to watch a hot shirtless guy say, “I came across time for you, [imagine him saying your name here]. I love you. I always have.”

Kissing Jessica Stein

This one hits on a lot of my own personal crap, so watching it is very therapeutic. Like the title character, I am Jewish, live alone in New York, have a day job in a non-artistic field and paint in my spare time, am a big reader, and have too much noise running in the background of my mind. I really like how it portrays a period in Jessica’s life in which she realizes she’s unhappy, takes a risky step to change that, and discovers a relationship that inspires her to change her life professionally and artistically.

Not to give away the ending, but it is moot whether or not the relationship between she and Helen lasts in a romantic way, because it brings her to a calmer and more artistically fulfilled place in her life, as well as to a true connection between them, regardless of its form.

Therapeutic!

Shallow Hal

I don’t know what it is about Shallow Hal, but I could watch it anytime, anywhere. It kind of has a positive message, and the characters are realistic, and they undergo personal growth, and in the end, good things happen to good people. But really, when it comes down to it, I don’t know why I love this movie so much. I don’t know, I don’t know, I really don’t know.

Waiting to Exhale

If cell phones were big when this movie came out, there’d be a lot of drunk texting in this film.

This is good to watch this with your single girlfriends and, like, 9 bottles of wine and an entire cheesecake. You can debate which of you is like which female character and whose ex is like which male character.

After drinking the vat of wine, you’ll all inevitably swear always to be there for one another and make a pact that you will not drunk text anyone that night. Unfortunately, you will each probably break that pact as soon as you get home, because life can be hard and being too perfect is just no fun at all.