Wayback Wednesday: Sleeping with Other People (2015)

A romantic-comedy that’s a little slept on. 

Okay, here’s the truth: Most of the time I’m extremely thematic when I choose the movie for my Wayback each week. For example I’ll go, “oh, Scoob! (2020) is coming out this week? I better choose Scooby-Doo (2002) as my Wayback.” I’m usually very organized. By the way, check out my reviews for those movies, here and here. Then there are some weeks, like this one, where I look at my A-Z list of reviews and go, “huh. I’ve never reviewed a single movie from 2015. Huh. Maybe I should do that.” It’s that type of inventive thinking that led me to choosing this week’s Wayback, Sleeping with Other People (2015).

Screen Shot 2020-05-25 at 1.31.44 PM
Credit: imdb.com / IFC Films

Written and directed by Leslye Headland, Sleeping with Other People follows Jake and Lainey, two college students who lose their virginity to each other and 13 years later, bump into each other again. They quickly bond over their mutual attraction and the fact that they both ruin every relationship they’re in by sleeping with other people. Jake and Lainey stay in touch, and what blossoms is a deep, meaningful friendship that they both can’t help but feel should turn into something more.

I’ve seen Sleeping with Other People a few times now and each time I watch it, I’m torn as to how much I actually enjoy it. When I first watched it I thought it was pretty good. The second time, I went as far as putting it on my list of all-time favourite movies. Now, after my third viewing, I’ve come to the conclusion that it’s perfectly fine. Sleeping with Other People is a wonderfully well-done little movie that definitely has more than it’s fair share of good points. One of which being that it’s brimming with more depth, originality, and overall charisma than your average romantic-comedy. Somehow though, despite dynamic dialogue, phenomenal performances, and dynamite direction, I can’t say that I LOVE this movie. Which is so weird, because dynamic dialogue, phenomenal performances, and dynamite direction are three surefire signs that a movie is made for me. It’s even a love story set in New York City! I go crazy for that!

Screen Shot 2020-05-25 at 1.29.43 PM
Credit: imdb.com / IFC Films

If you’re familiar with my reviews, you’ll know that the writing is always the aspect of a movie that makes it or breaks it for me. As mentioned, the writing in Sleeping with Other People is fantastic. As with most movies written and directed by the same person, Sleeping with Other People has a dialogue that feels totally unique. It pairs perfectly with the the way movie is shot and edited to create an overall cohesive tone, and by extension, a perfect execution of Headland’s vision. Headland’s use of dialogue is superb. It’s whip-smart and just as fast. Have you ever been to a party and met someone for the first time and after talking to them go, “oh my God, this is the coolest, funniest person I’ve ever met?” And then never see them again? That’s kind of what listening to each of these characters sounds like when paired with Headland’s writing. Sleeping with Other People may not have stuck as one of my all-time favourite movies, but it’s definitely one I’ll revisit just to get a crash course on establishing dialogue and tone alone.

The story itself starts off on a strong note, but I think loses steam the more it delves into the dramatic. I understand the drama helps add a layer of intrigue and conflict to a story, but I think Sleeping with Other People would have benefitted from some restraint. This movie is at its absolute best when Jake and Lainey are flirting with each other, hanging out, and developing their relationship. For me, the story comes to a halt when it switches gears to Lainey’s inability to let go of her former flame, and Jake’s business dealings. Do those things help flesh out the main characters? Sure. But do they also distract from what the most enjoyable aspect of this movie is? Absolutely.

Speaking of the most enjoyable aspect of this movie, let’s talk about Jason Sudeikis and Alison Brie as Jake and Lainey respectively. I’ve always thought these two were great. In every show or movie I’ve seen them in, they’ve been clear standouts who steal the show with their talent and charisma. Their lead roles in Sleeping with Other People are no exception. Sudeikis and Brie are both equally endearing, hilarious, attractive, and when the movie calls for it, pleasantly surprising as dramatic actors. Sidenote, if you want to see Sudeikis like you’ve never seen him before, check out Colossal (2016). He plays totally against type and it’s intoxicating  to watch. In Sleeping with Other People he plays the independent bachelor we’re all familiar with, but still makes it feel fresh with his own spin on the character.

Sudeikis and Brie’s chemistry is off the charts. Their back and forth is incredible to watch, and they compliment each other so well that I’d happily watch them pair up in any number of future projects. Both get the opportunity to showcase their true acting skills, but it’s undoubtedly Brie who provides the movie’s emotional punch to the gut. She’s an incredible actress. There were times I found myself laughing at her subtle delivery of clever one-liners, or her stupendous physical comedy, and then gobsmacked by the heartbreak Lainey endures. As much as I loved watching Sudeikis and Brie, I have to say, I loved the supporting cast just as much. Billy Eichner, Natasha Lyonne, Adam Brody, Adam Scott, and Jason Mantzoukas? They each match the energy of this movie and I love it!

Sleeping with Other People is well-written and well-paced. Each scene moves the story forward concisely and effortlessly, leading into another scene that does exactly the same. Jake and Lainey’s relationship is always evolving and moving along. Their storyline together never gets stale and the movie does a great job of keeping you invested in their shared storyline. You’re always interested in what’s going to happen next with them. That being said, I seem to recall more exciting, memorable things happening in this movie. I guess I was mistaken. There are maybe two wonderful scenes in the whole movie, and the rest is largely forgettable despite how well-made the movie is. When it comes to rom-coms, I want to close my eyes and be able to recall countless iconic scenes. As wonderful as Sleeping with Other People is at creating a cool rom-com that blends R-rated humour with PG-14 romance, it’s no When Harry Met Sally… (1989). By the way, check out my review for that movie, here.

Screen Shot 2020-05-25 at 2.03.16 PM
Credit: ew.com / IFC Films

I still really like Sleeping with Other People. It may no longer have a spot on my list of favourite movies, but it’s certainly worth a watch every once in a while. If you’ve never seen it, definitely check it out. Who knows? Maybe it’ll wind up on YOUR list of all-time favourite movies. As for me? I’m okay putting this rom-com to bed for the time being.

Have you seen Sleeping with Other People? What did you think?

Let me know in the comments or on social media!

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