josh dillon

Updated List of Imagines!!


Dillon Imagine

“Dillon, you dork! You know I don’t like being tickled!” You squealed, swatting him away with your hands. All you wanted to do was hang with your best friend for a few hours before meeting with Taylor for their new collaboration song. But, Dillon being Dillon, he wanted to annoy you with tickles. Outside, you were fuming. On the inside, you were fighting the urge to call him cute and kiss him. Yup. You caught that love bug, and it just so happens to be your best friend.

“Come on (Y/N)!” He taunted you. “All you have to do is say the magic words”. You roll your eyes.

“No way! Just stop tickling me!” He shakes his head and chuckles.

“Not gonna stop until I hear the magic words!”

“Ugh fine!” You huff in defeat. “Dillon Rupp is the sexiest, coolest, most awesome guy I know!”

“Preach!” he says and stops tickling you.

“Are you guys done doin’ it in there?” Taylor asks from behind the door. “I don’t wanna walk in and see naked butts or anything!”

Dillon rolls his eyes, not noticing your deep red blush. “Come in dude! My best FRIEND and I our fully clothed. Taylor waltzes in slowly, gaining pace as he sees you guys really are fully covered.

"Just making sure”, Taylor says, putting his hands up. “One can never be too careful”

“Yeah,” you say. “But one can be too annoying!” you smirk, high fiving Dillon. 

“But if you love Dillon, you can learn to love me too!” he says and you blush. 

“Yeah, we’ll see about”, you smirk. You check your phone; a new message! Opening it, you read the text aloud. “Josh wants to take me out tonight. Should I go?” you ask, turning to your best friend.

“Josh?” Dillon asks, incredulously. “Since when do you like Josh? He’s a total douche canoe! Sorry, (Y/N) but he’s not worth your time”.Your ears get redder and redder with anger. How could he say that? If you couldn’t date him, why not go out with someone else. 

“Not worth my time?” You say, your voice getting louder. “You know what’s not worth my time?” you get up and walk to the door. “Spending time with the person I love so much but will never get any farther than friends!” Slamming the door, you run down the hallway. 


Did she- did she really mean it? Damn, I really hope that’s true. “Where do you think she ran off to?” Taylor asked, worried. “The fans know her. She could get mobbed!" 

"I don’t know”, I say, rubbing my temples and closing my eyes in defeat. 

“Oh so now you don’t know (Y/N) good enough to know where she could be hiding?” Taylor asks, irritated. “You and (Y/N) go way back, like we do! I know you liked her ever since the 8th grade formal when you were each other’s first dances”.

“She doesn’t like me anymore anyway. You saw her run off!” I say, gesturing towards the door.

“Yeah I saw”, he says. “But I also saw how bad she wanted you to follow her”.

“You think if I told her, she’d be with me and not that Josh guy?” I ask, getting up to slip on my shoes. 

“Of course man!” he says, excited. “Does this mean you’ll finally grow a pair and ask her?” I roll my eyes.

“Oh shut up Caniff!” I smirk and race out the door.

“Go Dill Pickle!” he cheers. “Go get her!” I laugh to myself. Now the question is; “where is she?”. Looking to the elevator, I see the sign to the stairs. They’re nice and quiet, and when (Y/N) gets mad, she runs to the most quiet part of a place. I smirk and run towards the stairs.


How could I have been so stupid? I just told him I liked him and ran away! This is so pathetic! He must think I’m a complete idiot. Well, if he’s not gonna care for me, I have someone who does. I pull out my phone and dial Josh’s number. 



On the final RING, Dillon runs up the stairs. Panting, he comes to you and crashes his lips to yours. The kiss was passionate, as if he wanted this as long as you have. You run your fingers through his hair as he pulls you tighter, making you smile. This is finally happening. 

“(Y/N)” Dillon says, breaking the kiss. “You can’t go out with Josh. Not when you have someone who’s been waiting what feels like an eternity just to kiss you”. you blush at his words. Dillon does too. “If you love me like I love you, then be mine already!” he exclaims, kissing you again. 

“A hundred times yes!” you say, a wide grin on your face. 

“(Y/N)?” you hear coming from your phone. Crap! Josh was still on the line! “(Y/N)? Are you there?”

“Yeah hi Josh”, you say into the phone. Dillon gives you a confused expression. You wave it off. “About that date? Yeah I don’t think my boyfriend would like that”, you smirk and hang up. 

“Boyfriend huh?” Dillon says, his arms wrapping around your waist. “Sounds sexy coming from you”,he says cheekily. “But you know what’s even sexier?" 

"What?” you ask.

“If you kiss me right now”, he winks. You bring your lips to  his again. 

“I love you”, you say in breathy voice.

“I love you too” he smiles and pulls me as close as he possibly can.