Damon, Olivia, and Elena were on their way to Chicago after Elena had begged Olivia to go with knowing they may need her help. Olivia was never one to turn down a road trip, so she agreed.

"I sure hope we find him cause; it would suck if the last memento of Stefan was that crappy old necklace" Damon said.

"Damon be nice" Olivia said. "It's an antique Damon like you" Elena said.

"Hmm" Damon said and pulled a journal out. "Read this paints a pretty little picture of Stefan's first experience in Chicago" Damon said as Elena took the journal.

"It's Stefan's diary" Elena said. "Stefan has a diary" Olivia asked.

"I'm not gonna invade his private thoughts" Elena said.  "You need to be prepared for what you're about to see" Damon said.

"I've seen Stefan in his darkest periods I can handle it" Elena said and Damon took the journal back. "Here's one March 12th 1922" Damon said. "You just don't take no for an answer do you" Olivia asked. 

"I've blacked out days I wake up in strangers' blood in places I don't recognize with woman I don't remember" Damon said and faked a gasp.

"I'm shocked Stefan's not a virgin" Damon said and Olivia hit his head from behind the seat. "Eyes on the road grandma" Elena said and Damon focused back on the road.

"Fine back to my game tell me if you see a Florida plate" Damon said as Elena read the journal.

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Elena, Olivia, and Damon had arrived at Stefan's old place he stayed at when he was in Chicago. "Stefan could live anywhere in Chicago and he chose this" Elena said.

"There used to be an all-girls high school around the corner, but it shut down for attendance issues" Damon said.

"Oh, lovely a all you can eat buffet" Olivia said sarcastically. "If you're trying to scare me into giving up and going back it's not gonna work" Elena said. "Shh" Damon said.

He broke the doorknob and opened it as they all walked in. "Here we are Stefan's second personality home" Damon said.

"He obviously hasn't been here" Elena said. "Tour is not over yet" Damon said. "Okay y'all have fun I'm going to get a drink or something" Olivia said and left.

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Olivia had sat at the bar when Gloria recognized her. "Well look what we have here Olivia Lockwood" Gloria said.

"You know me" Olivia asked. "I knew your mother" Gloria said. "Do you know who she is I never knew her name" Olivia asked and then Damon walked up.

"Well look what the wind blew in last I heard you hated this place" Gloria said.

"Gloria if I knew you were gonna age like this I would've stuck around" Damon said. "I always did like you better, but I see your brother is still running in the wrong crowd" Gloria said.

"You've seen him" Damon asked. "With Klaus bad combo" Gloria said. "You know where they went" Damon asked. 

"They'll be back here later tonight they're out running a little errand for me" Gloria said.

"Gloria don't be a tease" Damon said. "Oh, shut up" Olivia said to Damon. "Hm never thought you run around with a werewolf" Gloria said.

"What kind of errand" Damon asked. "Mm I don't think so you may be cute but you're still a vampire" Gloria said. "You think so really him, him out of all people I don't see it" Olivia said. "I like her" Gloria said.

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Damon and Olivia went back to Stefan's old room where Elena was. "Finally, I called you an hour ago even Liv" Elena said.

"Make yourself presentable I know where Stefan's gonna be tonight" Damon said.

"I told you that I was practically discovered by Klaus, and you're worried about what I'm wearing" Elena said.

"I had an hour to realize what a bad idea it was to leave you here alone" Damon said. "It took you an hour to realize that" Olivia said and Damon rolled his eyes. "Process it and move on" Damon said.

"Are you okay" Damon asked after a moment. "Yeah" Elena said. "Okay good get dressed you're all road trippy and gross" Damon said.

"So, you know where he's gonna be" Elena asked. "He wouldn't have said he did if he didn't" Olivia said. "Yes, with Klaus, Liv and I will distract Klaus" Damon said.

"Excuse you he wants to turn me" Olivia said. "Right bad idea I'll distract Klaus and you and Liv deal with Stefan" Damon said.

"Okay thank you" Elena said. "But you're going to have about five minutes tops before that hybrid freak rips my heart out so, please tell me you can do this" Damon said. "I can do this" Elena said.

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Stefan had pinned Damon to the car using his vamp speed. "What is wrong with you" Stefan asked. "What is wrong with you" Damon asked shoving his hands off of him.

"You kill Andie one day you save my life the next what are you, good bad pick one" Damon said. "Klaus almost saw Elena today you have to get her out of Chicago" Stefan said.

"She's not going anywhere until she's got you checked into vampire rehab and on the mend trust me, I've tried" Damon said.

"She is the key to everything Klaus can't know she is alive" Stefan said. "What are you talking about" Damon asked. 

"She was supposed to die in the sacrifice, and she didn't now Klaus can't create any new hybrids his witch is seconds away from figuring that out and once she does, I have a feeling he's going to go back to Mystic falls and get Olivia tell Elena to go home and forget about me" Stefan said and Damon noticed Olivia and Elena. "Tell her yourself" Damon said and Stefan saw them.

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"Damon had long left to distract Klaus. "You shouldn't be here either of you" Stefan said.

"Yeah, well I'm a sucker for road trips" Olivia said. "Where else would I be" Elena asked. "What do you want" Stefan asked.

"Damon won't be able to distract Klaus for long" Stefan said. "Come home" Elena said. "I don't think it's that simple Lena" Olivia said. 

They had hugged and when Elena was about to stab him Stefan stopped her.

"Told you so but no one ever listens to the werewolf" Olivia said. "How much clearer can I make it" Stefan asked. "I don't want to come home" Stefan said.

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"Klaus is obsessed with airing these hybrids along with turning Liv the second he knows your alive he'll figure out why it's not working" Stefan said.

"Look I know you're trying to protect me and Liv, but I can't let you do it come with me Stefan please" Elena said. "And what do you expect if I do huh" Stefan asked.

"It's never gonna be the same Elena" Stefan said. "I know that" Elena said.

"I don't think you do I've left bodies scattered from Florida to Tennessee innocent people humans" Stefan said.

"Lexi found you like this before in the 20s and she saved you" Elena said.

"And you know what I did after that I spent 30 years trying to pull myself together to a vampire that's nothing to you that's half your life" Stefan said. "I can't give up on you Stefan" Elena said.

"Yes, you can it's done that part of my life is done I don't want to see you I don't want to be with you I just want you to go" Stefan said and left.

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Olivia, Damon, and Elena had got back in the car prepared to head home.

"You okay" Damon asked Elena. "Just drive" Elena told Damon and he did.

Lex here don't forget to feel free to comment and ask questions.