The I Love You Challenge

a/n: I used emails to update Chelsea because she was far behind...

Nov 4th, 2012
Hey Girls,
My date with Sidney Crosby went great and he invited me to go to a game tonight! It’s against Boston so I can check out the action for you Jamie. I think he really likes me already; I’ll be sure to take extra caution to make sure my father doesn’t find out. You know how he feels about me being with hockey players.
Hurry home if you want to even have a small chance girls!
Xoxo
-Chelsea

Nov 6, 2012
Hey,
I had a blast at the Penguins game yesterday which is pretty shocking. Lucky for me, Crosby scored two times so it was easy to flirt and the other WAGs were very accepting, thank God. We went out for a while after the game and he leaves for a five-day road trip starting on Tuesday so he’s coming over to my place tomorrow. Liz and Lissa: I hope you made it to your respective homes safely; Jamie: I hope you have safe travels tomorrow!
Xoxo
-Chelsea

Chelsea knew she had the lead and she was proud of it. Sure, it wasn’t a sport and she wasn’t guaranteed a win just because she had the earliest start but it sure was reassuring. Sidney was fun to hang out with which made the whole thing even more bearable. He was a dork and loved to joke around which refreshing from the cocky, airheaded, guys she usually dated. In fact, Chelsea liked hanging out with him so far and thought that they may be able to be friends after this whole thing blew over and she won.

As she was getting ready to have Sidney come to her apartment she received a text from Melissa.

Melissa: How am I supposed to find a kid who can’t drink? Does he go out with the team anyways? Does he have a life?
Chelsea: LOL. You might as well try going to a club/bar frequented by the Hurricanes. He might be a rule breaker or you could get introduced through his teammates. Want me to ask Crosby what he knows about Skinner?
Melissa: Yeah and while you’re at it you can tell him all about our bet!
Chelsea: I’d be sly about it! I’m not an idiot…
Melissa: No don’t even bother. I’ll figure something out.
Chelsea: Whatever you say. It was so weird to all be together the other night, right?
Melissa: Surprised Liz and Jamie didn’t try to bite my head off like the last time
Chelsea: It was Lizzie’s idea in the first place. And btw, I thought you were going to tell them about your brother?
Melissa: I was but I didn’t want to ruin the happiness…
Chelsea: Because you’ve always been a pillar of happiness! I’m calling BS, you chickened out.
Melissa: Shut up! I’ll tell them eventually!
Chelsea: Better tell them soon before they find out from another source
Melissa: Okay mom thanks for the advice.
Chelsea: JUST DO IT! I gtg, Crosby’s here! :)
Melissa: YOU LOSER

Chelsea didn’t like having to wait five days in order to continue winning the bet; especially while her friends got to continue. In Sidney’s absence from Pittsburgh Melissa had scored a date with Skinner and Jamie, the girl who everyone thought was a joke in this bet, had gotten a start with party boy Tyler Seguin. Chelsea was a little annoyed at Jamie for going with a guy who was all for everything she had fought against but it was also cool to see a new, competitive side of Jamie. The only person Chelsea had a lead on was Lizzie. Poor Lizzie was in the same hopeless situation Chelsea was in; waiting.

Sure Crosby texted her whenever he could and one night she called him after they beat the Tampa Bay Lightning but it really wasn’t the same; especially when Friday night came. First, it was Jamie’s cruelly sweet update. Not only was it too cheery but it was also shocking. Then Melissa’s update came an hour later.

Bitches,
Jeff Skinner is a hottie with a body and one hell of a goo kisser!!! Imma kick all ya’ll prude little asses at this shit. Put aside $50 baby!!!!
Not gonna bother with the lovey dovey crap because I know at least two of you still think I should be chillin in jail with my bro!!
-Lissa Skinner

Chelsea couldn’t help but spend a lot of time laughing out loud at that one. It didn’t take a genius to figure out that Melissa was so drunk. She went to grab her phone to text a reply to Melissa but instead chose to “reply all” so everyone could participate in the conversation.

Chelsea: Jeff Skinner is one hell of a good kisser? Someone must be drinking…Mrs. Skinner!
Melissa: Sorry that you can’t get the boy and the booze Chels. I even invented a new drinking game. Every time I think of Jeffy I take a shot!
Chelsea: and you are this drunk?
Melissa: Sorry you can’t get the booze and the boyz Chelsea!!!
Jamie: Maybe you should stop drinking now Melissa.
Melissa: Don’t fret honeybuns I don’t have a car to go driving in so Im stuck in my apartment and I won’t be “ruining” anymore lives
Lizzie: Don’t you have like a roommate or something who can take the booze away from you?
Melissa: I convinced daddy that a roommate would turn me into a bad little girl like my big brother. Worked like a charm.
Jamie: I’ve seen the effects of drinking firsthand and I think it would be the best idea if you stopped.
Melissa: Jamie you never went to a party unless college changed you and it was actually your dead boyfriend who suffered from the effects of booze. Just took two shots while writing that. LOL IM SUCH A LIFE RUINER.
Chelsea: I’m leaving now; play it smart Melissa.

Chelsea sighed and closed her laptop. If Melissa was telling the truth amongst all the drunkenness then she had kissed Jeff Skinner on their first date. The first stinking date. That put Melissa in first place. Yeah, Chelsea knew that kissing didn’t equal love; she had kissed plenty of men without ever loving them at all. Even still it was one-step that Chelsea hadn’t reached; putting Chelsea even further behind. It was then that she knew that the next time she saw Sidney she would kiss him.
***

Even though Sidney’s road trip ended that Saturday, Chelsea told him that she could wait another day to see him so he could rest. It took a lot for her to say that when all she wanted to do was see him so she could kiss him, you know, so she could jump ahead on this whole bet thing. Instead of seeing Sidney, she and her roommate Sarah decided to have their own sweatpants and cheesy rom-com marathon. While Chelsea was popping popcorn and Sarah was getting her cell phone from her desk in their room, there was a knock on the door. She had no clue who could possibly be stopping by on a Saturday night so she hurried to door. She looked through the peephole, per her dad’s request.

“Sidney!” she exclaimed thrusting the door open in shock, while smiling broadly. “I thought we weren’t getting together until tomorrow!”

“I’m sorry if it’s a bad time but I just couldn’t go one more minute without seeing you,” he said sheepishly while blushing. It was true. All week on the road he couldn’t stop thinking of Chelsea. He even played even better because it helped him do better. Now, as she stood in front of him, standing only in a baggy t-shirt and yoga pants and he still thought she looked gorgeous.

Chelsea was surprised to say the least but it was still a pleasant surprise. Then, when he said that he couldn’t go one more minute without seeing her she knew it was the perfect opportunity. She took a step towards him and leaned up to kiss him. It was short because she broke away quickly to go back into her apartment. As soon as the door shut, he began to kiss her again. Chelsea could tell Sidney was really enjoying it and she figured that if she was actually into him she would be too, it might even be romantic. He was a great kisser but she wasn’t really feeling anything besides excitement that she was finally back in the game.

“Chels, Jay just called and he wants me to come over to ‘talk’. Do you think this bra is sexy enough?” Sarah shouted as she walked out of the room staring straight down at her phone; completely unaware that Sidney was over. She looked up soon enough to see them kissing and gasped. “Oh my god! Sorry I didn’t hear the door!”

Sidney and Chelsea quickly broke apart blushing bright red and looked over at Sarah who was standing in the doorframe in only a very revealing, lacy, and pink push up bra and sweatpants. “OH MY GOD THE GUY YOU ARE SEEING IS SIDNEY FREAKING CROSBY?!?” she cried in complete disbelief. “Oh my god,” her tone was now full of realization. “Sidney Crosby is seeing me in my bra!” Looking mortified, Sarah turned and bolted back into the room slamming the door. Chelsea looked over at Sidney who was bright red and looked to be amused, confused, and embarrassed all at the same time.

“I’m going to go talk to her. Make yourself at home!” Chelsea told him before going to see Sarah. When she walked into the room, Sarah was standing with her arms crossed.

“WHAT. THE. HELL.” Sarah exclaimed as soon as the door was shut.

“I’m sorry! I guess you didn’t hear the door and I didn’t think you would-“

“Why didn’t you tell me you are dating Sidney Crosby?!” Sarah questioned obviously not caring about anything that just happened besides that.

“We aren’t dating and I knew you would freak out!” Chelsea replied defensively.

“It sure looked like you are and damn straight I would flip out! This is insane! Sidney Crosby just saw me in my bra! This has only ever happened in my dreams! Literally!”

“Thanks for giving me that mental image! Anyway, what were you shouting about Jay?”

“Oh right, so he just called and I’m going to go over to his place. I haven’t done laundry in forever and this is the only bra I have left. I think I got for prom night or something so I wanted to make sure it was sexy enough for him.”

“It’s a little too, um, preteen. I just did laundry, you can borrow that red one I got a few weeks ago that you wanted,” Chelsea told her rolling her eyes.

“Thank you so much! Now go back out there, but keep it in your pants before I leave ok?”

“Oh, shut up. That’s a lot coming from the girl who is leaving to go visit her ‘friend Jay’.” Chelsea said before going back out to Sidney who was awkwardly sitting on the couch.

“I’m so sorry about her,” she said sitting down next to him.

“I didn’t know you had someone else over,” he replied.

“Sarah is my roommate,” she explained. “We were planning on having a girl’s night in tonight but she’s ditching me. I’m sorry she overreacted she’s kind of a Pittsburgh puck slut to be honest. That’s why I didn’t tell her about you sooner.”

“Oh okay that makes sense. Maybe I can set her up with James Neal then, he usually goes for that type,” he joked.

“Don’t let her hear you; she’d probably take you up on it!”

Chelsea said and they both laughed. “You can stay here if you want to; now that she’s leaving.”

“Are you sure?”

“Of course! I love having you over,” she said softly leaning in closer to him. He leaned too and as soon as their lips touched for a second time. Sarah walked out.

“Oh my god you’re kissing Sidney Crosby! I can’t handle this!” She exclaimed walking over towards them.

“Sidney, this is my roommate, Sarah. Sarah, this is Sidney.” Chelsea said introducing them.

“It’s nice to meet you,” Sidney said as they were shaking hands. “Want me to sign your jersey?” he asked when he saw that she was holding a #87 jersey and a sharpie. She nodded rapidly and he signed it for her.

“Okay Chels I’m heading over to Jay’s now. Don’t wait up for me!” Sarah said after she put the jersey away.

“I’m not that stupid!” Chelsea replied as she left. “So,” she said turning to face Sidney. “I was going to watch 21 Jump Street but we can watch something else if you want.”

“No that’s a good one, I’m fine with it.”

“Awesome, I made popcorn we can have unless you’re hockey diet doesn’t allow for it.”

“No I can have popcorn,” he said smiling because she thought to ask.

“Lucky you. My dad always put his players on crazy diets.”

“Your dad coached?”

“He coaches the local high school team back in Michigan. He always had the craziest rules for his players; and me. I bet he would be furious if he knew I was with you right now. The number one rule was I don’t so much as look at them and they don’t so much as look at me. He doesn’t trust hockey players.”

“Well we’re looking at each other right now, you rebel.”

“You’re not my first offence honey.”

“But you just said…”

“Just because it was a rule doesn’t mean it was followed,” she said as she winked at him and hit the play button for the movie. As the movie went on the grew closer and closer until he had his arms wrapped around her and her head was resting comfortably on his shoulder.

Once the credits started rolling he began to kiss her before it escalated to full on making out. She pulled away after a while.
“I’m so tired,” she told him apologetically. “I should probably go to bed. Are we still on for tomorrow?” she asked as they both got up and he started to get his jacket on.

“Yeah, I’ll pick you up at 11?” he verified.

“Sounds great! I already can’t wait!” she said hugging him and giving him a small kiss before he left her apartment.
Chelsea could wait for the date; that was no big deal. What she really couldn't wait for was to email her friends about what had happened that night and she was even more excited to win the bet and the $150 that came with it. The other girls didn’t even stand a chance.