Matty, Kenzie, and Diane
KENZIE
Kenzie is based on one of my real-life best friends (such a shocker, I know). She's been with Lily from middle school to high school (and technically college) and is actually one of the first friends she makes after she moves to her new school. Kenzie is meant to be a very open and truthful person, you feel like you can tell your secrets without any judgment. She of course has strong opinions and comes off a bit direct at times, but she's never mean or cruel in any way. One of her flaws is that she can sometimes get a bit overwhelmed by her emotions and act on impulse before thinking something through. She tends to be very protective over her friends, especially Lily. Apart from all this she could be known as the life of the party and is someone who's loved by many for her charming personality. She's like a ball of energy but she could spark into a fire if pushed too far. When looking at how she deals with conflict, she usually approaches it head-on and fast. However, when it comes to situations with Lily in the play she backs off so as to not upset her or make things worse. She's mindful of her best friend's feelings, but as we see from her conversation with Matty, she always keeps an eye out even if she's not directly acting upon something. Kenzie is a true friend, through and through.
MATTY
Matty is inspired by a couple of guy friends I've had throughout the years in my life that I truly trusted despite their friend groups. When push comes to shove, they always try to do the right thing. Matty comes from an interesting group of friends like David and Jake. In middle school, it's subtle but clear that Matty is much closer with David and Jake, especially David. This is deeply intentional when they get to high school because there's a clear disconnect between Matty's values vs. David's and Jake's values. He almost digs into them at times because he can't believe who they're becoming so we see that slow distancing happening, especially as he starts to suspect David after Lily changes her mood entirely at school. He's very much an observer and keeps lookout like Kenzie, hence why they're fairly close and always in cahoots with each other.
It's interesting to point out how Matty doesn't appear to follow anyone around within the guy trio he's in. David will sometimes tag along to Jake and Jake has always followed around David, but Matty doesn't seem to ever fall into that pattern. It's also something that appears to make David and Jake more willing to insult or bash Matty before the school fight begins. Matty is his own person and is sure of himself, in short terms, he's already become a man and that's clear to those around him. Matty and Jake are trying to find ways to get themselves there and are envious of him because it looks like he didn't even try. He didn't idolize Mr. E the way they did so he was in a way, already ahead of them, and didn't have to cope the way they did.
We do need to talk about how Matty gets into the fight with David. Not only is this the first time we see Matty angry, but it's also the first time we see him directly confront David. However, it doesn't appear in the script that Matty is afraid of David. The intention of Matty's conflict is that he can't seem to let go of the friend he used to know in David. This guy he's become is just so hard to fathom and he finally realizes after he sees David almost hit Lily in the hallway, that he is not the guy he knew anymore. He takes out this anger and frustration out on David in this fight, but quickly breaks away so he doesn't change who he is as a person as a result.
DIANE
The character of Diane is inspired by one of my present-day best friends who went to high school and college with me, however, for the play I made her the same age as me (she's older in real life). She has this energy that is so motherly and warm. You could argue she's the "mom best friend", but for this play that doesn't apply within her friend group. She has somewhat sarcastic tendencies, but all in all is very kind and open-minded. She enters later in the story but still holds just as much value in Lily's life as Kenzie does. She sort of becomes the closest friend Lily has once they become roommates and Diane gets more one on one time with her. However this doesn't mean Kenzie is removed from the picture, she just can't always physically be there as we hear from Diane saying they tend to call Kenzie once in a while at school.
When Lily and Diane get to college, she immediately starts to notice these depressive habits Lily has but doesn't want to confront her until she realizes that Lily has ripped out the months in her calendar. Assuming they started school sometime in August, Diane has had all this time til December to notice Lily more and more preparing for the unthinkable. It can be safe to assume that this might be the first time Diane has ever been close with someone like Lily who has dealt with so much. At first, she might've thought Lily was just clearly traumatized, but her mind might have not gathered that she was really considering suicide. When it comes to depression and suicidal tendencies, the signs aren't always clear or noticeable if you've never met someone who was going through it. Diane gradually gets more scared til the point she breaks down in front of Lily. All she wants to do is support Lily, but she also partly blames herself for not noticing much sooner when she met Lily. After Lily comes clean, Diane becomes this shield in a sense and tries to remain optimistic so that Lily can be too. She means well, but it's not wrong to assume that she's terrified of Lily falling into that dark place again.