1922, Chicago
Over the years, Stefan has built quite the reputation for himself, he together with Lexi who he met not long after he left Mystic Falls.
The duo travelled together and became best friends just like the series.
Stefan still had the reputation of a Ripper but only to his enemies and those who stand on his way and not some innocent humans who he feed on.
He also managed to control his bloodlust over the years as he did not want go about mindlessly killing people and making Lexi do what she always does in the series.
Today, he is in Chicago where he is going to meet two originals, Klaus and Rebekah together with his new friend, Alphonse Gabriel Capone, Al Capone for short, who is going to help him build his vampire army after this Chicago operation.
He is not here to just meet up with the original siblings but also here for someone else, actually two until one of them is invaluable anymore.
He is alone with Al Capone as Lexi had something to take care of could not be able to make it but he told her where to find him.
"So what are we doing here? You said you are going to make me like you but why are you delaying it, come on, I can't wait anymore" said Al Capone who was promised by Stefan to turn him into a vampire and help him take control over Chicago underground business.
"Oh that I will, in fact I can do it right now" said Stefan as he bit his hands and fed Al Capone his blood before snapping his neck and killing him.
After waiting for a few hours, Al Capone woke up and Stefan told him to follow him as they made their way to hidden club.
"Am I like you now?" Asked Al Capone.
"Shut it, will you? And no, you are not like me yet, you have to feed on human blood to complete your transition which this place happen to have in surplus"
Stefan said as he smiled and look at the bustling club where everyone were dancing and having the best time of their lives "go on, take one of the women and go to a hidden place and feed on her to complete your transition, don't kill her and make sure you compel her to forget what happened by looking directly into her eyes and after you are done, come meet me" said Stefan as he left Al Capone who has already left to do what he was told the moment he left.
Stefan scanned the entire club but did not find any of the originals, so he waited for a while but they did not show up.
"Sigh, they are not here yet, I will have to wait for a few more days then"
After saying that, Stefan decided to mingle around and make some friends who would spy for him and tell him if they ever saw any one who fits the description to the people he told them about.
And that's how Stefan spent a month waiting to meet the original siblings but he always end up not even seeing a glimpses of their shadow talk less of meeting them.
He even made friends with the owner of the club, Gloria, a witch and a very semi - powerful one at that and one of his targets.
They exchanged few pleasantries and had few nights together as Stefan wanted her to trust him while not knowing that this was all a ploy if Stefan.
Since he couldn't make her loyal to him on a whim, he will have to go old school on her which is working out just fine.
On this faithful night, Stefan and Al Capone walked into the club where he could see Gloria performing on the stage.
Gloria spotted him and winked at him "guess who my eyes just spied, ladies? Looking for a good time, Mr. Salvatore?" She said as she announced his presence in the club.
"Save me a dance, Gloria and maybe make some arrangement for my friend here Al Capone" Stefan said as he and Al Capone walked down the stairs and Stefan wanted to take a drink that was coming to him but someone beat him to it.
"Hey, lady what do you think you are doing?" Said Al Capone as he wanted to rush at her, the woman who took the drink meant for his sire and friend.
But before he could do anything rash, Stefan held him back and smiled "don't do anything stupid, that woman can rip out your heart and you would not know how that happened" he said as he looked at one of the original siblings, the original sister, Rebekah Mikaelson.
"Well, that's a pleasant surprise, you seem to know about me. Now tell me, who are you and how do you know about me?" Said Rebekah trying to compel Stefan who was on Vervain.
Over the years, Stefan has been taking Vervain as he knew that this is the only way to prevent being compelled by the originals.
"That wouldn't work on me, I am on Vervain, ever since I knew about the originals, I have been taking Vervain to avoid being compelled" said Stefan as he moved his face closed to Rebekah who thought he was coming for a kiss but to her surprise he moved to her ear "just like a situation like this, but don't worry, I am not the enemy here but a friend, a friend you can trust"
With that Stefan left along with Al Capone who was still looking at the shocked Rebekah.
With that, Rebekah became intrigued with Stefan and said nothing without about it to her brother, Klaus.
After that, Rebekah and Stefan became very close but Stefan did not just have Rebekah jump unto his bed easily like what he did to Gloria but built his relationship with her and wanted to make it real and not just some fling he had in Chicago.
For him, Rebekah was someone who deserves to be loved and even if he can't give her the type of love that she wants, then he can at least let her feel it for the time they are here in Chicago.
And that's how the love story of Stefan and Rebekah began in the heart of Chicago.
A few weeks later
Stefan and Rebekah were feeding on a woman who was moaning from the pleasure of having her blood drained by two vampires.
After they had their fill, Stefan and Rebekah kissed each other for a few minutes until Stefan had a hold of the famous Necklace that belongs to the original witch.
"It's beautiful" said Stefan.
"A witch gave it to me, supposedly it's magical" said Rebekah while still kissing Stefan.
"And is it?" Said Stefan.
"It brought me love, didn't it?" Said Rebekah who did not stop kissing Stefan.
"It's late Rebekah, we're leaving"