Disclaimer: I have and make no claim to any Hannah Montana copyright. Non-HM characters and settings are my own.

Author's note: In the gum episode (Season 1), Lilly states she has a brother. That doesn't work for this story, so here she is an only child. Also, Lilly and Oliver aren't close friends (in the Then section). I have read several stories which have them as neighbors, not so here. I put Lilly in a condo-this is California, after all. One last thing-I use the name of an author on this site (Broken Oken), as a nickname for Oliver. I hope no one is offended and that doing so breaks no rule. Dear Stupid, by that author, is the first long fanfiction I have read. It is terrific, as are the author's other stories. I apologize to the author. This story consists of nineteen chapters.

Before Miley: Now, Then, and Now Again

Now

Jackson pulled his car to a stop by the curb in front of the spanish-fantasy style condo complex and turned his head to look at his sister.

"Well thank you, I guess" she said, with a hint of annoyance in her voice.

"Gee, you're welcome" he replied, matching her annoyed tone. "You can call Dad to come get you, I'm going out tonight."

"Big plans with Thor? I know you can't have a date."

"Better than Oliver settling in for an evening of girl talk."

"You and Thor are likely going to spend all night seeing who can spit farthest. Oliver gets to hang out with TWO pretty girls."

"Get out of the car."

Miley smiled as she did. Score one for me, she thought. As her brother drove off, she walked into the complex and to the unit where her best friend lived, and rang the doorbell.

"Hello, Ms. T, is Lilly here?" She asked that knowing the answer, but followed the polite format for showing up at someone's door.

"She and Oliver are in her room, go on up. And please tell her I'll be leaving now, and that my cellphone will be on all evening should she need to speak to me."

"I will, have a good night Ms. T."

"You too, Miley."

The brunette girl climbed the stairs, familiar from almost three years of visits, and walked to Lilly's room. The door was opened wide, as the rule both here and in Miley's home required should a boy be present. She began speaking before even entering.

"Jackson wouldn't even let me drive here. I have my permit so he could have he just doesn't want to do even that much for me. Hi Lilly, hi Ol-Oliver."

The blonde girl, in tee shirt and sweats, with bare feet, was seated crosslegged on the bed. The brown haired boy, in tee shirt, jeans, and sneakers, was on a rolling desk chair turned around so he could lean forward on to its back.

Lilly noted her friend stumbling over the boy's name, he seemed to have missed it.

Miley kicked off her sandals and as her friends greeted her sat on the bed, matching Lilly's crosslegged pose. She also matched Lilly's clothing, wearing a tee shirt and sweatpants.

"We're all ready bored" Lilly said, yawning as if to emphasize her statement. "Any ideas what to do?"

"TV?"

"I say videogames" Oliver threw in.

"We have the place all to ourselves until around midnight. I'd rather do something we don't do all the time."

"All right Lilly, but what would that be?" asked Miley.

"I don't know. Maybe Truth or Dare? We never do that, and there's no one to walk in and see us doing anything stupid."

"I'm ok with that as long as the dares don't get nasty" Miley said. "How about you, Oliver?"

"Fine with me, but who starts?"

"I claim home field advantage to go first. Oliver-Truth or Dare?"

The boy had played this game all of twice before, and had always chosen dare, preferring to look foolish rather than answer an embarrassing question. He also knew that Lilly enjoyed seeing him do silly things on her command.

"Dare."

"Kiss Miley's feet."

"Eww, what happened to no nasty?"

"I said just kiss them, not suck on her toes. The tops of her feet will do. C'mon Miley, let those dogs out."

The blonde noted the blush on her friend's cheeks as the brunette stretched out her legs, falling back onto her elbows as she changed position. Oliver rolled the chair he sat on along the bed and took Miley's right foot in his hands, raising it up as he lowered his head to meet it. Not just a peck, not hurriedly at all, he pressed his lips to her foot, taking his time as though this were a normal, everyday occurance. He set down her foot and rolled away.

"I said feet. That was foot."

Oliver rolled back and reached out while lowering his head, just missing being kicked in the eye as Miley's left foot shot past his face. He secured her foot and planted his lips on it, trying to equal his previous effort as Lilly would certainly point out any difference.

The blonde again noted the light blush on her friend's cheeks, and as the boy released the held foot thought-well I was right. Just a little bit of a crush but it's there.

"My turn" said Oliver, "and it's for both of you."

"What? No! One person at a time. You can't do two."

"Yes I can. I'm always outnumbered but this time it's going to work for me, not against me. It's only fair. Both of you, decide now-Truth or Dare?"

"Truth," said Lilly.

"Dare," said Miley.

"Mi, he's going to dare us to make out with each other. It can't be dare."

Miley looked shocked. "He would never! Oliver, tell her. You would never ask us to do that. Tell her."

Oliver's grin had an almost evil cast about it. Miley's jaw dropped as if he had suddenly grown horns and a tail.

"I told you. You just refuse to see what a guy he is. You need to open your eyes."

"Oh come on. It's even a popular song now. And you can't deny girls sometimes practice kissing with each other."

"We don't! Why would you think we would?" Miley asked.

"Besides," Lilly added, "why would we practice on each other when we have an almost acceptable set of boy lips available?"

This question was rewarded with deep flushes of color on the cheeks of both her friends. Two crushes, she thought. I should start thinking about how to get them together. There's really no reason for me to be against it.

"Truth, Oliver, truth" Miley said, all but snarling the words at the boy. It was an overreaction which should have told him something, but which again he seemed to have missed.

"Ok" he said sharply.

What a donut, Lilly thought. He is just so thick about girls, even when he's crushing on them.

"I can't think of anything really good to ask. How about this? What teacher do you each have a crush on? It's not a great question, but it is personal."

Lilly smirked. "It is pretty bad. You could have asked us our bra sizes, or something else we never would tell you. Crushes was weak."

"Can I change my question?"

"No!" That said loudly by Miley.

"At least you have an idea for next time," said Lilly. "But then again, you've been in both our bathrooms, I wouldn't put it past you to have snooped through both our hampers and found that out by now."

"I never! I would never do anything like that. You know me better than to think that."

"Yeah, the sad thing is, I know you wouldn't. Ok, on to the question. Let's answer it together. Three, two, one..."

"Mister Christy!" both girls said.

"I'd have thought at least one of you would come up with an original answer. Every girl in school crushes on him."

Mister Christy was one of the social sciences teachers for their grade. The one all the girls and most of the boys wanted for that class. He wasn't especially handsome, just an average thirtysomething. His appeal was in his actions. He was a photographer, he spent summers on nature photo assignments. He had been published in several magazines, he had even won awards. His classroom was decorated with prints and even some actual awards. He always told his students that if he could do it, so could they. The boys admired him, the girls crushed, annoying even the most fannish boys.

"I really am dissapointed in both of you. There isn't a more ordinary choice on Earth."

"Don't distract me, it's my turn" Miley said. "And it's for Lilly."

"Don't even dream of dare, I'm not kissing donut feet."

"Ok Lilly, here it is. I want to know, with full details, everything about your first real, full-out, boyfriend-girlfriend kiss. And I do mean every detail." She leaned forward, focusing on her friend like a hawk studying it's prey.

Lilly was completely surprised. She hadn't even imagined that question being asked, and couldn't understand why not. It was an obvious choice for a sixteen year old. Her face reddened as she stammered out half words and gutteral sounds, and continued reddening. The expression on her face became one of fear, a bright red fear.

For Miley, the fun of the game suddenly evaporated. Her friend was in actual distress, caused by that question. With a shock Miley realized that in spite of numerous dates with numerous boys, Lilly might never have experienced such a moment. That she might be abjectly embarrassed at having to admit so in front of the boy she so frequently ridiculed for his constant, inept, almost painful attempts at being a ladies' man. The question went too far. She was hurting her friend.

"Wait! I withdraw the question. I have another one, a better one, don't answer that one."

She turned to look at what Oliver was doing. If he was laughing at Lilly, or even looked about to laugh, she would thump his head but good.

Oliver wasn't laughing. His face was as red as Lilly's, and he too had fear in his eyes.

"What-what's going on here? Is there something between you two I don't know about? Are you keeping something from me? We're best friends, what are you not telling me? Someone should start talking."

"She's not going to give up Lilly, there's no point in keeping it from her now."

Lilly bowed down her head, buried her face in her hands, and began to speak.