Sleeping with Other People. That’s a thing you do after you’re done sleeping with another person, right? Stop me if you’ve heard this one before: boy and girl meet, boy and girl have moment together, boy and girl fight every natural instinct to get together, but we know how this can and will end. This film isn’t out to change the romantic comedy genre so much as put a spin on it.
The director, Lesley Headland, assembles a pretty strong cast of talented people that are on their a game in this well-written tale. There’s a lot of buildup to what we know will be the film’s conclusion, and even though it may be predictable, in this case, the movie’s ending is unearned, in my opinion. But one step at a time. This is Sleeping with Other People.
The film begins in the year 2000. There’s a lot of commotion going on in this particular college dorm hallway. Banging on one of the doors is Lainey, played by Alison Brie, who doesn’t look any more like a college student here than she did on Community, but that’s neither here nor there.
Anyway, Lainey here is trying to get the attention of the person in the dorm, but to no avail. She’s nearly hauled off, but saved by one of the students that covers for her. The savior is our other protagonist, Jake, played by Jason Sudeikis, who also doesn’t look any more convincing as a college student than Brie. Okay, I’m off this for now. I could spend all day here.
Jake brings Lainey to his dorm room. We learn that Lainey, dressed in quite the skimpy outfit, is currently involved with one of Teacher’s Assistants. In fact, she’s been failing a class on purpose just to get some solo lessons. Jake finds it funny, but he’s also a tad disgusted since he believes that Lainey deserves better.
On the roof, the two talk of sex. College students have that on the brain a lot, don’t you know? Lainey asks Jake what sex is like, and Jake describes it as kissing with your entire body or shooting heroin into a moist environment. Yeah, Jake hasn’t had sex at all yet, but I applaud his creativity. A warm moment ends up going south a bit with poor choice of words, but things turn around when the two consummate the moment.
We cut to the present day. A woman named Hannah, played by Margarita Levieva, storms out of Jake’s place. She’s furious because she was interested in a casual relationship, but Jake went and screwed Hannah’s best friend, Sarah. Margarita isn’t the best of liars and it’s here where Jake showcases his use of logic. Nothing was set in stone about their thing and she’s only incensed because the other woman happens to be her best friend.
Jake gets her to calm down and just when it looks like the two are headed back to his place, she pushes him into traffic. Always look both ways before being pushed into the street.
Lainey’s dinner with her date, Sam, played by Adam Brody, goes south fast. Sam is very talkative and into Lainey for honest reasons. He’s even talking about their possible future together. However, Lainey needs to present a letter to Sam and she’d prefer to read it aloud and uninterrupted. She mentions that, at the advice of a therapist, she’s been attending a program for…let’s call them love addicts.
Oh, and she cheated on Sam. We don’t learn who, but Sam makes a scene and assumes that the other guy is his brother. Lainey blames herself for this, as she should, but Sam is sure to be easy on her. She’s not an addict, he says. She’s just a whore. When Sam leaves, Lainey heads to the ladies and texts a man named Matthew Sovochek.
Following this, Lainey sits in on a meeting of sex addicts. She leaves during one particularly colorful tale from a man who liked having things stuffed in his ass and had both male and female partners. It’s unfortunate that we don’t get to hear more of this tale because it’s being told by Billy Eichner, better known as Craig Middlebrooks on Parks and Recreation, and he’s as expressive here as he is on that show.
But the point of this scene is to reunite Lainey with Jake, who also happened to be attending the meeting. The two catch up, with Jake learning that Lainey teaches kindergarten kids. They plan to reconnect. Jake even mentions that he’s on Facebook, but only after does he realize how odd it is to say that out loud.
We then see Jake hard at work. He and his associate, Xander, played by Jason Mantzoukas, are about to have their work dissolved through a powerful executive named Paula, played by Amanda Peet. Xander wants this signed right now, and while Jake wants to talk terms and conditions, he soon signs. He’s also very forward and asks Paula on a date, despite her being recently divorced and having a kid. She’s confused. Jake could have anyone in the world, so to pick her is odd.
Lainey arrives at a gynecologist’s office for her appointment. Said doctor performing on her is the aforementioned Matthew Sovochek, played by Ben Wyatt himself, Adam Scott. An almost unrecognizable Adam Scott, at that. Lainey tells Matthew that she can’t see him anymore, and he actually agrees. In fact, he recently proposed to his now-fiancé, Emma.
The last thing Lainey needs is for Matthew to delete his number from her phone because she can’t bring herself to do it, but one thing leads to another and the two end up having sex on Matthew’s desk.
Later, Lainey rants to her lesbian friend, Kara, played by Natasha Lyonne, that she needs to stop having sex. Kara tells Lainey that she may fall under having sexual anorexia. That’s a thing, I suppose.
Jake, Xander, and Xander’s wife, Naomi, played by Andrea Savage, have drinks at a bar. Lainey joins in on the fun just as the four toast to virginity- the married couple knowing that Jake and Lainey lost their virginity to each other. Lainey, a bit embarrassed by this, leaves, but Xander convinces Jake to pursue her.
There’s no push into traffic this time. Lainey tells Jake that when the two met up for this tonight, she had hoped it would be a proper date. Jake did not see it that way at first, but he’s fine with making a date out of this. However, a change of scenery is necessary.
And here, we get the first of many Jake and Lainey visits to a local Chinese restaurant. Jake asks why Lainey was ever interested in Matt. She explains that she thought he would choose her, even though she is psychotic and is going to meetings for sex addicts. But, she points out, Jake is attending these meetings as well.
His reason for going is because his girlfriend gave him an ultimatum: go to the meetings or their relationship is over. He went, but she dumped him anyway. Jake doesn’t know how to end relationships and he doesn’t want to say that he can’t commit to someone because he’d come off like an asshole. But being a bad guy is better than being honest.
When the date ends, Jake realizes that he has the urge to fuck Lainey. How could anyone not want to fuck Alison Brie? But realizing that this thing between them can’t progress to physical contact, and that they’ve ruined all of their past relationships, Jake and Lainey come to an agreement that this friendship can go no further than that. They establish a system that includes a safe word to say whenever there’s great sexual tension. Jake shoots down avocado, Guam, and noodle salad, but since he cringes when Lainey then suggests Dick in a Mousetrap, the safe word is henceforth mousetrap.
And I’m sure they’ll never get together by film’s end.
Sleeping with Other People is, at its core, a romantic comedy. It has traits and tropes of your typical boy and girl will inevitably get together tale, but it’s much more than that. This is a story not just about love, not just what it means to be in love or our perception of love, but also trying to maintain their friendship above all else. Many critics have compared this film to When Harry Met Sally. I’ve yet to see that film, despite how long it’s been out, so I can’t speak to the similarities.
Director and writer Leslye Headland knows what makes for a good romantic comedy and how to interject drama into the lives of characters that feel real. A lot of that has to do with their blemishes. Jake and Lainey are not perfect at all. They’re addicted to sex, they don’t know how commit to people, they aren’t the nicest of people, and their lives aren’t where they’d want them to be. I’d argue that Jake appears to be in a better position than Lainey at times, but I’ll get to that later.
This film asks what we want most in a relationship. Do we want someone who’s just a quick fix, or something long lasting? If you just want to get your rocks off, the quick fix may sound preferable, but it won’t mean much in the long term. To quote from Hitch, “falling in love is so goddamn hard.” Some people, like Jake, can find a match in no time, but if the connection doesn’t go beyond the physical and you’re not interested beyond that, there’s no reason to commit.
And that’s something that neither of the main characters can do: commit. Jake goes from one woman to the next, but instead of owning up and saying that he doesn’t want a relationship, he takes the coward’s way by cheating or giving a woman reason to leave. He’s too afraid to say that he can’t commit.
At the same time, Lainey can’t commit to anyone because she’s too hung up on the one that got away and isn’t interested in her beyond sex. As such, she ends up burning bridges with any man who wants to have a connection with her because she’s stuck in the past. She can’t move on and accept that there are more men beyond college flings.
So we have two characters that want happiness, but no idea of how to find it. Logic and typical movie plots dictate that these two should get together. First off, while they lost their virginity to one another, they’ve also been friends for a long time and don’t have that sexual urgency that they have towards others. They just want to remain friends. Right.
As someone who’s never been in love, I find that to be a pretty bullshit premise because it’s inevitable that two people of equal attraction will fall in love, despite every attempt to mask their feelings. It’s the only issue I have with this film’s otherwise simple premise. You can’t expect characters with a bond as deep as Jake and Lainey’s to stay friends forever and the audience is smart enough to think beyond ‘Will they, won’t they’ because we know they will. Audiences have come to expect that happy ending, so what matters is making the journey interesting.
This is one of the reasons I hold a show like You’re the Worst in high regard. There, we know that Jimmy and Gretchen will, against their better judgment, become a couple, but the show is more on how they navigate the tricky waters instead of where the journey ends. And creator Stephen Falk took the romantic comedy genre and turned it on its head with that show. But enough about that. I could talk all day about that show.
But sometimes, the solution to your romantic issues may be right in you. “The one” may not always be out there in the distance so much as right in front of you. But you can’t just go for them from the start. That would be too easy and the movie would be far too short. But Jake and Lainey have that chemistry already.
After all, they lost their virginity to one another after realizing neither of them had crossed that line. They already have a connection binding them, and then later in life, they still act like the best of friends. What I think this film is saying is that in order to have a strong relationship, you need to start with an even stronger friendship. Sure, that’s obvious, but too often do films have characters fall in love at first sight without any sort of conflict. That’s too easy.
It’s thanks to Headland’s script, as well as the chemistry between Jason Sudeikis and Alison Brie, that the slow build to Jake and Lainey becoming an actual item feels real. They shoot the shit at restaurants and text one another about their flings like they’re still in high school.
In addition, there’s a bit of self-awareness and meta humor at play here with the characters making sure that they’re not getting too attached since they’ve seen this scenario play out many times before. That and both Jake and Lainey acknowledge that they do and act like a genuine couple, but deny that they are one. They try to resist the urge to fall back into old habits to show that they’ve grown up, as hard as that is. At one point, Lainey receives an unexpected phone call from Matthew.
Jake takes the phone away from Lainey, telling her that she has to move on, and Lainey gets upset about it because there was a missed opportunity for a quick romp. In a moment of weakness, she almost succumbed to the urge for that gratification she so desperately sought, even though she doesn’t need it. The problem is that she doesn’t realize that she doesn’t need it. And at the same time, Jake doesn’t need to go from woman to woman and doesn’t see yet that his relationship problems would go away if he was more honest and didn’t try to talk his way out of his screw-ups.
But it’s because Jake and Lainey fit like a glove that keeps them away from each other for so long and drives them together. One of the film’s central main points is about people being in a potentially damaging relationship with someone they like, versus a happy relationship with someone they don’t like. It’s a risky move to take. Instead of giving ourselves to someone who comes off as nice and wants to be with us, we turn our attention to the one we can’t have because we feel whole with them.
This means giving up the chance to be with a person who does want to be with you, leaving them to the sidelines when they’ve done nothing wrong, as Jake and Lainey do several times in the film. This makes them feel a tad unlikable in my book, though part of that could be due to the writing, because they blow off decent people since the plot demands that these two get together.
Despite the contrivances of the film and what it’s asking you to accept, I still enjoyed much of Sleeping with Other People. There’s some great humor throughout, with two particular memorable moments of Jake and Lainey showing up at a children’s birthday party on ecstasy.
Or another memorable scene where Jake uses a bottle and his fingers to show Lainey how to masturbate because she’s never done it before. And she’s a woman, so I can believe that.
I also really enjoyed the chemistry between Jason Mantzoukas and Andrea Savage as Xander and Naomi. When you put older, married couples alongside younger protagonists, there’s the fear that they’ll just be stuck-up, bitter, and resentful of their friends for living the lives they once wanted. Not so here. Xander and Naomi do want to relive their youth, but they’re not an angry couple. They’re fine where they are and still find time to fool around like they’re college kids.
It’s a nice way to show that there is life beyond marriage and it can contain happy moments. In addition, they also serve as mentors to Jake and Lainey with advice that benefits in their favor instead of just trying to push them together. Also, stay for the credits, as Xander and Naomi have one of the film’s best and extended comedic moments.
The leads are just as entertaining. Alison Brie makes for a great, damaged woman that somehow manages to put a smile on despite her less than great situation. As the film progresses, Lainey learns to have respect for herself, as she spends most of the movie carrying a torch for Matthew.
Again, she’s not perfect and I appreciate that she both has a lighter side and learns life lessons as the movie progresses. She admits her flaws and insincerity, but she also strives to better herself by applying to medical school. So she may be in a rut, but she’s sure as hell not going to remain there.
Most of what I’ve seen Jason Sudeikis in has been comedy, whether it’s the Horrible Bosses films, Saturday Night Live, or It’s Always Sunny in Philadelphia. But here, he’s still funny, but he’s given some range with a slightly more serious character. Jake is charming and quick with witty lines, but when it comes to Lainey, he knows his boundaries. When he gives her advice or encouragement, it’s not done with the intent of getting into her pants.
And like Lainey, he goes through a character arc when he lays off his womanizing and tries to find something stable. In addition, he’s not immune to Lainey’s beauty. He shows obvious jealousy when Lainey dates some, but not all, guys because she discusses things that he thought were private. There were no terms established as far as that goes and he does come off as petty, but better that he show some form of emotion, rather than act as if he’s unable to be turned on by Lainey.
With all this said, it might seem like I don’t have any issues with the movie, but I have one major qualm: this movie’s ending is completely unearned. Again, it’s clear that Jake and Lainey will get together by film’s end, but the way in which the film wraps up and shows total disregards for some characters just to pair Jake and Lainey is unbelievable and makes the two of them look very unlikable in my book. I won’t spoil it, but the actions Jake and Lainey take cannot and should not be excused just because they’re the main characters and we want to see them become an item. It left a sour taste in my mouth and when the film ended, it was all I could think about as opposed to all of the good that came before it.
So Sleeping with Other People is still a good movie regardless. It’s a different approach to the romantic comedy genre that does a lot of things to set it apart from typical films of that category. It’s helped by a fun script and great performances from the cast. At the end of the day, do we want to fail with someone we like or succeed with someone who we don’t like as much? It’s interesting to think about, but it’s just too bad about that ending. It put a damper on an otherwise contrived, but enjoyable film.