Title: Five Times Jeremy Gilbert Got the Girl & the One Time He Didn't

Summary: same as the title. Vicki, Anna, Katherine, April, Hayley, and Bonnie. Some AU/AR

1. Vicki

When freshmen year had started was when Jeremy started figuring out what his body wanted. He'd make excuses of why he stayed in the bathroom for so long but he knew that clearly everyone knew what he was doing.

So he started looking for a girlfriend to ease his tension, then his parents died.

His fascination with Vicki Donovan started way back when he began to think girls were pretty. She was two years older than him but something about those pretty curls in her hair made him want to pull on them. So he would, she would scream and state that she hated playing with Elena's kid brother, and run away making one of her famous dramatic exists.

But never in a million years did he think that Vicki would like him back. But in a drug haze he looked into the brunettes eyes and smashed his lips into hers. She smelt like weed tasted like alcohol with a hint of bubble gum.

The summer before his sophomore year was the best summer of his life.

It was true Vicki was a little too wild and a little too easy but letting Vicki Donovan deflower him was the best move Jeremy ever made.

He didn't have to sneak out, his parents were dead, and both Jenna and Elena had other shit on their minds besides dealing with him that he merely just had to walk out his front door. He would walk into the Donovan's home and straight to Vicki's room.

Jeremy finally got a girlfriend. It didn't matter that he was using this as a way to cope or that maybe the drugs lead to Vicki's decision to be with him. Either way he had Vicki and she had him and that was all he had ever wanted.

2. Anna

When Jeremy met Anna he thought she was a nosey girl. He was pretty sure that she was forcing them into a friendship, which she was but he gave her a chance and eventually she grew on him. Anna was an echo; a fire inside Jeremy's soul one he could not let go of even if he tried.

So many moments so many glances kept Jeremy questioning about her.

Then he figured it out Anna was a vampire. As much as he wanted Anna he had wanted Vicki more so when Anna said she would turn him he went with it.

But now he can see Anna's ghost. She's all alone and he can be the one to pull her back into this world. Jeremy doesn't like to admit it but he knows deep down that being with ghost Anna had been more of a relationship then being with her when she was alive.

It's only her and him now not her and him and him thinking about Vicki. She is there but not really he can't touch and hold her anymore. But then it happens and he can. Their kiss isn't like any others they have had before. This one is sincere and had been building up ever since he started to see her again.

He knows he can't love a ghost for the rest of his life but when he finally says goodbye to Anna he knows he will always love her.

3. Katherine

Before Damon leaves Katherine and Jeremy to search for Mikael by themselves he states. "You partners in crime behave."

And so far they are doing a good job.

Though he can't but help stare at her a little longer than usual after all she looks just like Elena and there is also the factor that she kidnapped him.

"Careful Mr. Gilbert," Katherine states in her snarky way. "Would Elena approve?"

But he sees her staring right back at him. He knows it's mostly because she wants his blood but Jeremy secretly knows Katherine probably has a lot of fetishes. One probably involves her pretending to be Elena and kissing him or something. Why else would she be into having both Salvatore brothers?

He likes playing along. An accidental touch, random sexy eyes he has seen Damon do so well and even a couple of slip ups by calling her Elena. The thing is Katherine is enjoying it.

"You want to kiss me?"

Katherine's face drops as she shakes her head. "Why on earth do you think that Gilbert?"

Jeremy gives her a look as he takes a step closer, and closer now with only an inch between their faces. Katherine's chest is moving rapidly even though she really doesn't need to breathe. That's when he knows he's got her.

Jeremy steps back. "Gilbert one. Pierce Zero."

Katherine, using her vamp speed, comes to Jeremy smirks and snaps his neck. "Now we are on an even playing field."

4. April

When his mother told him that Pastor Young was coming to dinner he freaked. It wasn't that Jeremy was a bad kid that god would strike down. It was the fact that April Young was home from boarding school for the summer.

This was the same April who pestered Jeremy as children, the same girl who he would write notes to while not paying attention to her father's sermons, the same girl who annoyed the hell out of him most of the time.

But his father and Pastor Young were good friends so that meant he would put up with April for the summer. That is till she walked thru the door and Jeremy realized that April Young got hot.

Though Jeremy was going to be a senior he hadn't much experience with girls. He tried dating Sarah for awhile but that ended in disaster. He thought he could ask Elena for ideas but she was in her own world with Matt and already packing to go to Whitmore.

No Jeremy was all alone on this one. He still tried to avoid asking his father about girls and dating though the topic came up a lot when he walked in on Jenna and Ric that one time. But he did have his Uncle Ric. Alaric became his history teacher as a sophomore when Ric moved after his late wife's death. Eventually Jenna met Ric and the rest was history, ironic enough.

"You seriously want my advice?" Ric chuckles linger over the phone line.

Jeremy doesn't have time to whine that he doesn't understand why his aunt and uncle had to move to Colorado. All he wants is help but Ric doesn't seem to get that. So he hangs up on him.

His mother mentions it at dinner. Jeremy denies that he hung up on his uncle, 'I said bye.'

One weekend Elena invites a bunch of friends to the lake house, Jeremy tags along. He knows it's more of a one last party before everyone leaves for college, everyone but him.

"Everyone's leaving this sucks." April huffs as she sits down next to him. "And here I'm going to Mystic Falls High this fall and everyone I know will be gone."

Jeremy smirks as he looks at April.

She gives him a look. "What?"

"Looks like I'll get to pester you like you loved to do to me when we were kids."

April eyes linger on him before she looks to the ground smiling.

Yeah Jeremy knew how he was going to spend his last year at Mystic Falls High.

5. Hayley

Hayley Lockwood was a vindictive girl who came off snobbish and was a spitfire with her words. Jeremy had known Hayley for all of this life. Their parents were friends, their siblings were friends but they were not friends. Granted when they were young they would play with each other most of the time it ended with Hayley making Jeremy cry but no less they could both count on each other at lame Founding Families' events.

Hayley stated whatever she thought and most of the time it hurt a lot of people's feelings. But Jeremy remembers after his parents died that one day when he was in the town square looking at his father's office that she had came up to him giving him a hug.

"Looked like you needed it."

After the Mayor died Jeremy wanted to find a way to help Hayley. No one should go thru losing a parent alone but he never found the right way to do that. She kept insisting that she was fine. Instead he spent his time trying to help Tyler and steal the moonstone from the Lockwood family.

But here he was sitting in the Salvatore's study with Hayley who just found out about the supernatural.

"So my brother's a werewolf and so is my uncle and unless I kill anyone any time soon I won't go all hairy?"

"Yeah pretty much."

"If I kill vampires will that turn me?"

"You want to be a werewolf? After everything we just told you?"

"Hey if everyone else gets to fight evil why can I?"

Over time, Klaus coming to realize that Tyler had a sister who was un-triggered, Tyler leaving yet again, Caroline and Hayley fighting and not to mention Hayley's best friend was now Rebekah Mikaelson things kept building up for the young Lockwood.

Jeremy had things piling up too with losing Ric and becoming one of the five but here they were thrown together in this mess.

They sat outside the Gilbert Lake house waiting for Matt to arrive with the pizzas; Damon was off on the phone making kissing noises to Elena.

"You know you have gotten hot."

"Why I would thank you if you just didn't imply that I wasn't hot before."

"Seriously Jer. The new hair cut. The bulging muscles. Why else do you think I came to slayer camp 101?"

"I thought you came so Klaus didn't put you on house arrest until he can turn you into a hybrid?"

"Rebekah's right you are clueless."

Hayley lungs over the picnic table, her animal instincts kicking in, and grabs Jeremy by his t-shirts and crashes her lips to his.

Jeremy's last grasping thought as his lips move in junction with Hayley's is that Rebekah was right he was clueless.

6. Bonnie

Jeremy thinks he might have gotten back together with Bonnie if he hadn't died. Now he's roaming around ghost jumping to different places. He finds himself inside his childhood home as his corpse is burning inside. But he always finds his way back to her.

He had always known Bonnie Bennett; she was his sister's best friend and now his ex-girl friend. And just as everything was working out between the two once again he has to die. He wonders if Jenna felt this way or if Jenna even roamed around for awhile. Because seeing everyone you love falling apart is breaking his heart.

He misses the times, the awkward glances the lingering looks. But Bonnie isn't herself and she can't see him. She can see Silas posing as him but she can't see a ghost. Elena's words phase into his mind, 'you can't love a ghost for the rest of your life'.

Then the veil is dropped and he can see them. He can see her. The whole time he tries to go on pretending like he doesn't have a million thoughts racing through his head of what he wants to say to her.

In the end before he has to leave he goes to her. The kiss is his way of saying goodbye, of saying that he's sorry for messing everything up, he's so sorry that he died and that he's very much still in love with her.

Her kiss brings him back to life.

When he goes to run towards her, to pick her up and spin her around thanking the God that is Bonnie Bennett for saving his life once again her hand touches his face.

"I can't feel your hand."

She tries to tell him that she will be taken care of, 'I have the witches my grams', that they can still talk, 'You can see ghost we can talk whenever we want', the words that Elena told Anna replay in his head, 'he can't love a ghost for the rest of his life.'.

"No!"

"I'm going to be okay. I promise"

He stands there and cries watching her leave. He will keep Bonnie's secret but he's letting her go. No late night ghost chat. No meeting in abandon houses. No more doing magic together.

Because Jeremy Gilbert now knows that he can't love a ghost for the rest of his life.