Brett- You and Brett were always flirting with each other, but never went out together on a real date. In class he was flirting with you. Mr. Harris caught you two talking and gave you both detention. Brett was trying not to laugh when Mr. Harris almost tripped after he gave us detention. When class was over you and Brett walked together. Then you asked something you were dying to say for weeks now. "What are we?" You questioned.  "What do you mean y/n?" "You know like are we dating, or" And then he kissed you it was the best kiss you've ever had in your life. "y/n would you like to out with me on a real date and be my girlfriend?" He asked smiling like he knew the answer "I would be honored!"

Derek- You were best friends with Scott so he took you to meet Derek. It was very awkward because you could just tell he didn't like you. He always made rude comments to you. About a month later you were forced to see Derek again. It was going okay considering what usaully happens. Then he made one snide remark and told me I looked ugly today. I left the room and didn't say anything. Once  i got outside i started crying and I heard Scott yelling at Derek from outside. A few minutes later i heard Derek come outside and he apologized. I glared at him in response. "Y/n I'm really sorry i messed everything up you know. The only reason I'm mean to you is because i really like you." And with that he kissed he a real kiss too like he was trying to make up for what he said earlier. He then asked me if i would be his girlfriend. I said yes smiling.

Isaac-  You and Isaac weren't dating but he asked you to prom you gladly accepted and wore a beautiful pink dress. Isaac told you how pretty you looked and you headed off to prom. You guys knew each other so it wasn't awkward at all. You guys arrived at prom and danced the whole night. Finally a slow song came on and you guys slow danced. And at the end of the dance Isaac kissed you it was the most cutest moment ever considering it was your first kiss.

Scott- You and Scott were very close friends and you came to watch his lacrosse game. As you got there you sat down at the cold bleachers. Scott was on the field  warming up passing the ball to Stiles. The game started and it was intense you were at the edge of your seat cheering for Scott. It was the last period and they were tied 5-5 with 10 seconds left on the clock Isaac passed it to Scott and he was running to the opposite team's goal. Scott jumped over someone and threw the lacrosse ball into the net and the buzzer did it's usual sound that indicates the games over. I ran over to Scott and hugged him congratulating him on his big win. He twirled me around and then kissed me. It was unbelievable. He was so gentle and sweet.

Stiles- Stiles and you were dating for about a week but you liked him ever since 7th grade. He walked you home from your third date. You had such a good time with him. When you got to your doorstep he tucked a piece of hair behind your ear and kissed you. It was a nice surprising.

Liam: You could tell that Liam was nervous about your first date. He had always been clumsy and awkward, but tonight had brought it to an all time high.
He had already taken you to a movie and now he was taking you to get frozen yogurt.
"Have you ever been here before." He asked you looking over his shoulder.
"No, but it looks really good." You grinned. "I've wanted to come her for a while now."
"Well, you'll love it, you get to build it yourself-" he then tumbled in to a chair and you burst out laughing.
"Oh my god!" You said in between fits of laughter.
"Help me up." He said, totally embarrassed.
Still laughing, you leaned over and grabbed his hand. Instead of pulling him up, he pulled you down on top of him. Now it was his turn to laugh.
"Dunbar!" You scolded.
"What?" He grinned.
"That was uncalled for you jerk!" You laughed.
"I'll make it up to you." He promised,
"How?" You smiled.
"Like this." He grinned and leaned in.

Isaac: Sitting on the bleachers with Allison and Lydia on Fridays nights had become your usual Friday night. Supporting your best friend Liam, they always had games on Friday.
You cheered as Liam got the ball and started running towards the goal. A defense blocked him so he ran around the back of the net and rolled the crease. Getting a final goal. You all cheered as they announced that Beacon Hills had won the game.
After the game, you waited for Liam to come out of the locker room. He was giving you a ride home.
He smiled when he saw you, "Y/n!" He said squeezing you into a hug, "Thanks for coming!"
"Always." You chuckled, "Nice goal at the end."
"Thanks." He said slinging an arm around you as you began to walk down the hall, "We have to celebrate the win, let's go watch some movies at my house.
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You snuggled into his couch, wrapping the blanket closer around you. You were freezing. Isaacchuckled when he walked in and away you all wrapped up.
"What're you doing?" He asked plopping next to you.
"I'm cold." You explained.
"So am I." He grinned grabbing the blanket off of you. Then he draped it I've the both of you. Pulling you into him. He was being very touchy today, you blushed thinking about it. You'd always had somewhat of a crush on Isaac
"Who said we could share?" You asked with a smirk.
"Me. This is my blanket after all." He smiled. "Plus your my girl, so I choose who you sit with. And I choose me." He stated.
"Your girl? I never agreed to that." You said leaning into him.
"This might." He said and leaned down, pressing. His lips to yours.

Parrish: Sniffling through the isles of Walgreens was not how you planned to spend your Friday night. You were suppose to go out with Jordan, but obviously that wasn't going to happen. You and Jordan had recently taken the step out of the friend zone.
You sighed and called Jordan, in your weak, crackly voice, you cancelled your first date. You grabbed the cough medicine and cough drips and headed out of the store.
•••••••••••••••••••••••••••••••••••••••••••••••••••••••••
When you're sick what you do is lay on the couch and binge on tv shows and movies. So you scrolled through Netflix looking for a new series to start watching.
Right as you clicked the beginning to the first season of Gossip Girl, there was a knock at the door. You stumbled over to the door and opened up. There with a bright smile on his face was none other than Jordan Parrish.
"Jordan?" You croaked out, you didn't have much of a voice left.
"Hey, y/n. How're you feeling?" He asked.
"Like crap." You sighed and saw the bags in his hands. You pointed to them.
"Oh! Yeah, I thought that maybe since you weren't feeling to well I would come over and take care of you."
You smiled and let him in, "you're the best." You commented before going back to your spot on the couch and resumed watching Gossip Girl.
He walked over a bottle of Gatorade in his hand and a package of Popsicles. "I brought treats." He grinned and layed next to you.
"Can I have them please?" You begged, your throat yelling for a cold drink.
"Only if you give me a kiss." He teased.
"You'll get sick." You warned.
"No I won't." He grinned before kissing

Theo: First kiss preference: Scott, Stiles, Derek, and Isaac.

Scott: Sitting on the bleachers with Allidon and Lydia on Fridays nights had become your usual Friday night. Supporting your best friends Scott and Stiles, they always had games on Friday.
You cheered as Scott got the ball and started running towards the goal. A defense blocked him so he ran around the back of the net and rolled the crease. Getting a final goal. You all cheered as they announced that Beacon Hills had won the game.
After the game, you waited for Scott to come out of the locker room. He was giving you a ride home.
He smiled when he saw you, "Y/n!" He said squeezing you into a hug, "Thanks for coming!"
"Always." You chuckled, "Nice goal at the end."
"Thanks." He said slinging an arm around you as you began to walk down the hall, "We have to celebrate the win, let's go watch some movies at my house.
•••••••••••••••••••••••••••••••••••••••••••••••••••••••••
You snuggled into his couch, wrapping the blanket closer around you. You were freezing. Scott chuckled when he walked in and away you all wrapped up.
"What're you doing?" He asked plopping next to you.
"I'm cold." You explained.
"So am I." He grinned grabbing the blanket off of you. Then he draped it I've the both of you. Pulling you into him. He was being very touchy today, you blushed thinking about it. You'd always had somewhat of a crush on Scott.
"Who said we could share?" You asked with a smirk.
"Me. This is my blanket after all." He smiled. "Plus your my girl, so I choose who you sit with. And I choose me." He stated.
"Your girl? I never agreed to that." You said leaning into him.
"This might." He said and leaned down, pressing. His lips to yours.

Stiles: You could tell that Stiles was nervous about your first date. He had always been clumsy and awkward, but tonight had brought it to an all time high.
He had already taken you to a movie and now he was taking you to get frozen yogurt.
"Have you ever been here before." He asked you looking over his shoulder.
"No, but it looks really good." You grinned. "I've wanted to come her for a while now."
"Well, you'll love it, you get to build it yourself-" he then tumbled in to a chair and you burst out laughing.
"Oh my god!" You said in between fits of laughter.
"Help me up." He said, totally embarrassed.
Still laughing, you leaned over and grabbed his hand. Instead of pulling him up, he pulled you down on top of him. Now it was his turn to laugh.
"Stillinksi!" You scolded.
"What?" He grinned.
"That was uncalled for you jerk!" You laughed.
"I'll make it up to you." He promised,
"How?" You smiled.
"Like this." He grinned and leaned in.

Derek: Snoffling through the isles of Walgreens was not how you planned to spend your Friday night. You were suppose to go out with Derek, but obviously that wasn't going to happen. You and Derek had recently taken the step out of the friend zone.
You sighed and called Derek, in your weak, crackly voice, you cancelled your first date. You grabbed the cough medicine and cough drips and headed out of the store.
•••••••••••••••••••••••••••••••••••••••••••••••••••••••••
When you're sick what you do is lay on the couch and binge on tv shows and movies. So you scrolled through Netflix looking for a new series to start watching.
Right as you clicked the beginning to the first season of Gossip Girl, there was a knock at the door. You stumbled over to the door and opened up. There with a bright smile on his face was none other than Derek Hale.
"Derek?" You croaked out, you didn't have much of a voice left.
"Hey, y/n. How're you feeling?" He asked.
"Like crap." You sighed and saw the bags in his hands. You pointed to them.
"Oh! Yeah, I thought that maybe since you weren't feeling to well I would come over and take care of you."
You smiled and let him in, "you're the best." You commented before going back to your spot on the couch and resumed watching Gossip Girl.
He walked over a bottle of Gatorade in his hand and a package of Popsicles. "I brought treats." He grinned and layed next to you.
"Can I have them please?" You begged, your throat yelling for a cold drink.
"Only if you give me a kiss." He teased.
"You'll get sick." You warned.
"No I won't." He grinned before kissing you.

Theo: Theo was failing chemistry. So of course you offered to help him out, being the good friend that you are.
He came home with you after school one day so you could help him prepare for the next test.
You set your bag down on your bed and patted the spot next to you so he would come and sit down. He obligated and you opened up the text book.
You quizzed him for hours. Until he had it all down. Until it knew that he was going to ace the chemistry final coming up in a few days.
He grinned at you, "I can thank you enough, really, y/n, you're the best."
You shrugged. "I benefit from this too, you know. I got to study for the final and I got to spend time with you. I always love hanging with you."
He smiled, "I feel the same way."
"Really?" You asked.
"Yeah. I like you, y/n. I like you a lot."
"I like you to, Theo." You said and took the leap. You leaned into him and firmly pressed your lips to his.

Preference not mine. Credits to the owner.