The first girl Miles kisses is Chelsea Matthews behind the school when he's nine. It's really just a peck, but it still sends fireworks through Miles' head and a chill up his spine because Chelsea giggles in the girliest way that he's only heard in cartoons. And he's just a little boy but he can't believe that he made someone giggle like that, like they were happy. He used to be able to make Frankie laugh when she was still a baby by blowing raspberries on her stomach and she would laugh to no end until his mother told him that he was just going to wake Hunter, who was a very cranky baby.

Chelsea runs away from him so fast when it's over, runs to go and tell all of her little friends who giggle exactly like she did. They all keep looking back at Miles and falling into hysterics, like he's the funniest thing ever.

Miles kisses both of Chelsea's friends, Martha and Elise, during that week. He and Chelsea agree that she is his girlfriend, but Martha and Elise are her best friends so they can kiss Miles whenever he wants. He isn't necessarily sure how he feels about the kisses but all of the cool guys on television kiss lots of girls and Miles wants to be cool like them.

Miles's first real girlfriend is in the fifth grade and her name is Josephine Wilcox. She's the prettiest girl their age and all of the other boys like her – including Winston - but she likes Miles. "Every other girl likes you! Why do you have to like her?!" Winston yells at him after Miles tells him that they're going together.

"Because I just do,"

But there's something powerful about it. Josephine is gorgeous and funny and popular and desired by everyone and she wants Miles. His own parents don't even want him around and she does. She's powerful, and she wants him around. He doesn't know if he even really likes Josephine. Sure, she's nice but he's never really liked anyone besides thinking that they were cute before. And still, it's almost not even a question that Miles start going with her, even though it practically breaks Winston's heart and he doesn't talk to Miles for a week.

Josephine breaks up with him when Cindy Jones passes Miles a note in class telling him to circle 'yes' if he likes her and 'no' if he doesn't. Miles doesn't even like her, but he circles yes. Josephine finds the note in the trash and dumps him publicly.

He's going out with Cindy the next day.

Brandon Jace is the most handsome boy Miles has ever seen and he makes him laugh so hard that he can't breathe and he's really good at sports and he's just all around amazing. He hangs out with him and Winston starting in sixth grade and Miles tries to be around him as much as possible. He brushes up against Brandon accidentally on purpose, especially when they're in the locker room in gym class. Winston makes a joke about it once, about how Miles always stares at Brandon, but Miles chooses to ignore him.

He doesn't know how he can ignore the feelings though, especially when he has a very vivid dream about Brandon one night and wakes up covered in semen. Miles thinks for a second that he might be gay because he definitely has a crush on Brandon. Being gay would actually be pretty great for him, considering that he's heard his father complain about the 'fags' living down the block from them a thousand times. Being gay would just be a whole new thing to piss his father off and Miles honestly he loves it. He's twelve years old and the thought of enraging his father is delightful to him.

But he's not gay because he sees his father's young assistant Carol bend over and the sight of her large breasts hanging out of her shirt makes him pop a boner. He really shouldn't be angry that he's not gay because it'll make his life a lot simpler, but now he's just confused because he still likes Brandon.

But Brandon moves away before he can ever really figure anything out.

His first blowjob is from Monica Crawford a few months later. She's about a year or so older than him and has somewhat of a reputation around the middle school. She comes up to Miles during lunch one day when he's messing around with Winston and says simply, "I like you," and he's taken aback by how forward she is, but smirks and says "Really? Interesting."

"Interesting," she says back and she asks him if he wants to go to her house with her after school and of course he says. Winston won't shut up about the things he's heard about Monica, about how she's apparently had sex before. It just makes it better for Miles, even though he doesn't really respond to any of Winston's blabbering. He can't believe his luck, that someone that cool and that experienced would want someone who like him, who his entire family describes as a screw up who can't do anything right.

Monica's bedroom is like a child, it's covered with dolls and teddy bears and baby pictures of her. Miles feels weird staring into the eyes of her barbies while she goes down on him, but he can't help it. This is his first sexual experience that doesn't involve his own hand and he doesn't know how to enjoy it because he doesn't feel anything except lust. He just wants to feel something so desperately, but maybe nothing will ever be better than this. Maybe having someone who wants him is the best that life will ever get.

Monica wipes her mouth on his polo after he comes and gives him a kiss. She asks him to hang out again the next day, and the day after that and so forth and so forth. Each time, she just goes down on him. They don't talk much and he leaves after it's over. Monica's more of an accuaintence then a friend, and to most people, it might seem weird but Miles doesn't know how to have friends. His only friend is Winston, he's never felt a need to have anyone else in his life.

But still, when he hears Kyle Marks talking about how Monica is the "Blowjob Queen" and then his friend Anthony Chambers call her a slut, Miles punches both of them in the mouth. It's in the middle of class too and Winston has to pull him off of them and he immeaditely gets sent to the principal's office and he gets suspended for two days.

Monica doesn't blow him again because Kyle spreads a rumor that Miles is the one who called her a slut. Everyone believes it, even though there's witnesses and Miles doesn't bother correcting them. He knows the truth.

He wants someone to love him. He's fourteen when he decides that and he's practically desperate for it. Winston is all he has and he doesn't get physical affection from him. The only physical affection he ever gets is from his mother, when she kisses him good morning and good night. He doesn't count the make out sessions with the girls on the cheerleading squad or the blowjobs from whoever will give them to him. Miles wants real love, real affection. He wants for someone to care for him, to forgive him for his mistakes and not think he's a screw up.

So he tries with Sarah McGuinness first. He actually takes her out a date and asks her questions about her life and even picks her a flower from a vase in his house. Sarah laughs at everything he says even though he's not funny and she goes on and on about how handsome he is, and Miles can't really say anything to that because the one thing he knows he's good at is being handsome. Sarah and him go together for two months before he starts crying in the bathroom one day and Winston tells her about it and she gets freaked and dumps him.

Next is Linda Fazer. Miles showers her with gifts, gives her everything she wants because she makes him laugh, and her hands feel nice on his back. She's the first girl he ever goes down on and she comes so fast and so loudly, that he thinks he may have found something else that he's good at. However, Linda only seems to keep him around for that reason: has him give her oral almost every time they're alone. He finds out she's had a boyfriend in another town for three months and breaks up with her about a month in.

By the time he loses his virginity to Alex Beck, Miles thinks he's finally found love. No one has sex when they're not in love, right? But Alex is four years older and tells him that even though he's an eighth grader he's like the hottest boy ever and he asks if there's anything else about him she likes and she shrugs and says "I guess." Miles would never admit it, ever, but after she says that he's sad for the rest of the day and cries himself to sleep that night. He can't even enjoy his virginity loss like a real man because he's so upset that he isn't loved by the girl he lost it too. And it not doesn't even matter if Miles didn't love Alex, because he could learn to love her if she loved him. He would've treated her so well, like a fucking princess, but she didn't love him.

And the next day when Winston asks him what sex is life Miles just says "good" and goes on with his day.

He gets sent to boarding school for his freshmen year in high school. Miles is pretty positive then that sex doesn't equate to love, but having as much of it as possible will. Being close to a girl, their naked bodies against each other, warm and sweaty, is the closest he feels like he'll ever get to being close. And then he makes sure to always cuddle when they're done because that's what couples do in movies and Miles likes to pretend for just a little that he has a nice romantic life.

But no one will ever love him for who he is.

The girls all seem to like him there and he isn't sure why, because he knows he has a reputation but his lines always work on them and they always smile and giggle like little girls just having their first kiss. It's exhilirating, watching each one go from loving the idea of a bad boy that they can change, to realizing that that's all he is. They don't like his flaws, they just like the idea of them.

One thing Miles always wants to come across in his relationships (if you could really call them that) is that he loves women and he respects women. He doesn't want anyone thinking that he's just a typical misogynist who goes through women just because he wants a good time. Well, Miles does want a good time, but he likes to treat women the way that he'd like someone to treat him. Like they care about every word he says, like flaws don't matter.

Miles gets expelled from boarding school for starting a fire. He still claims he didn't start it (he did) but that doesn't matter because no one will ever believe him.

He meets Maya Matlin while he's smoking pot outside of a concert and she's exactly his type. A good girl with a thirst for adventure. But something that's never happened to hi before, happens. She goes from liking him to hating him within just days. And she spends the entire summer telling him how much she can't stand him and claims it's just because he "kissed" Tristan and then started going out with Zoe. But Miles knows better – she likes the whole bad boy routine but she just won't admit it.

When they actually get together, it's nice for a bit and Miles thinks that this is like a whole new world for him. He tries for Maya, he doesn't have to just throw a few lines at her and she throws herself at him in return. They don't have sex. They make out, but they talk a lot more. He talks about his feelings and she listens. She talks about her own dark past and he listens.

But then Miles loses it, which shouldn't be a shock to her because he feels like he's been on the edge of losing it for years now. He holds a gun to Zig Novak's head. It's fake, and Zig beat the shit out of him but Maya takes Zig's side. Zig is selling drugs, he's stuck with the bad kids in the rubber room, he's in love with Maya and cheated on his ex with her. He's a huge threat and he shouldn't be because he's a loser.

But he isn't crazy. And that's why Maya chooses him in the end. Actually, she breaks up with Miles for what seems like the thousandth time because he almost made out with Zoe at the party she was assaulted at. But she's still hanging out with Zig when Miles knows he's done far worse.

Maya ended up being just like everyone. She liked the idea of him and wanted to change the actual him, make into him someone who wasn't crazy.

Miles doesn't really have a problem when he starts dating Tristan. He's always known that he likes boys – well, since Brandon Jace – and he's been jerking off to gay porn for a couple of years. Confirming his sexuality to himself or anyone else isn't a big deal, all he cares about is having someone who doesn't care how many times he's screwed up and is just happy to have him around.

But Miles is far too focused on his own issues to really focus much on Tristan himself. His father is abusing him emotionally and now physically. He has to constantly worry about the twins, wondering whether or not he can protect them and knowing he can't. He's anxious all the time, there's always a weight on his chest. But Tristan doesn't notice a thing. So Miles just keeps smoking pot all the time to calm his nerves, to tell himself that everythin's cool. And that's when Tristan notices because he gets to spend less time with him.

They're making out one day and Miles is really genuinely happy because he likes that Tristan accepts his flaws. So he tries what he did so many years ago with Alex Beck, and he pulls apart and asks him why he likes him. And Tristan shrugs and smiles and strokes his arm and says "You're hot,"

And Miles gives up yet again.

He dated Zoe Rivas when he first came to Degrassi and it was only because they were both hot and attracted to each other and wanted someone to kiss. But things are different now. Miles isn't with the crowd he was with during his and Zoe's messy breakup. Zoe's being ignored by her power cheer girls because of the oomf chat scandal. They fall back together slowly. They develop a good friendship and Miles likes it. He's more quiet than he used to be, has given up on using his lines to pick up girls – or boys. He's reserved and gentle and Zoe seems to like that.

They don't get together until the summer because Zoe's been avoiding him because she's "busy." He takes her sailing and she talks a lot, keeps asking him questions about his sexuality and then moves on to questions about his parents, and while Miles answers her, he'd rather be kissing than rehashing his difficult life. But he has a lot of fun with Zoe. They enjoy the same sorts of things and she tells really funny jokes that make him genuinely laugh.

Things don't last too long. After the bonfire when she tries to have the threesome with Grace, they go back to Zoe's house and she locks the door of her room and pushes him down on the bed. She's going so fast and Miles is worried, he keeps asking her if she's okay every five seconds because he's worried. He knows what happened to Zoe, and he doesn't want to bring back any painful memories for her. Zoe requests that he go down on her and it's so random and out of the blue that he pauses and she turns bright red and tells him to go away. But then she tells him to come back right away, and Miles asks her twice more if she's sure (because she's been upset about Grace since she left) and she practically yells that she is. He eats her out and she comes (although he's pretty sure she faked it) and asks him to go home.

He does.

Next thing he knows, it's over.

Esme Song offers to help him with his dad in exchange for friendship. Friendship is a foreign concept to him, so he's confused by what she means, but to Esme, friendship means fucking a crazy amount of times in a lot of different locations. It also means lots of drugs and crazy nights out doing god knows what. She's sinister and he knows sometimes that she's manipulating him, but he can't really care because he needs the drugs so badly. He can't function without them.

They skip class together so often that they're really only there for English – Esme says that he likes it, so he should attend it – and sometimes Gym, although they spend that class sitting in the bleachers making fun of Hunter's lame friends. Esme is very guarded and only lets it down when she's super high, but more often than not she sits on his lap and hides the grin on her face when he plays with her braid and she tells him how proud she is of him for his writing. Plus, she's seen him naked so many times that he feels like there really isn't anything he has to hide from her. But mostly, he just begs her for drugs, anything and everything, as much of it as possible.

By the time he finally cracks and his mother discovers what's been going on, he breaks up with Esme. Miles does it gently, knowing that Esme is a lot more fragile then she acts like she is but she hides it and snarks at him before leaving.

She fakes a suicide attempt. She says she did it to get his attention and for the first time, Miles thinks that she's actually being genuine. Esme is crying real tears and telling him how he's the one she trusts, how she wants them to run away together. And while Miles does care about her and wants to take care of her, he has to take care of himself first.