Chicago one Imagines

By SuperWinchester1967

210K 3.2K 80

These will be imagines about whoever I write about so nothing specific 😊 More

What to expect
Disagreement »» Conner Rhodes 🚑
Brush of death »» Jay Halstead 🚓
First Date »» Kelly Severide 🚒
Worth it »» Will Halstead 🚑
Pet names for each other
One drunk night »» Matt Casey 🚒
The big day »» Ethan Choi 🚑
Yours»» Jay Halstead 🚓
Already gone »» Connor Rhodes 🚑
Dating Kelly includes 🚒
Dating Will Halstead includes 🚑
Dating Matt Casey includes 🚒
Dating Jay Halstead includes 🚓
Dating Conner Rhodes includes 🚑
Dating Ethan Choi includes 🚑
The new girl»»Kelly Severide 🚒
One Year»»Will Halstead 🚑
Lunch date »» Matt Casey 🚒
Reunited »» Ethan Choi 🚑
Happy Birthday »» Jay Halstead 🚓
The night shift »» Conner Rhodes 🚑
A promotion »» Kelly Severide 🚒
Love sick fool »» Antonio Dawson 🚓
Antonio Dawson catch up 🚓
Spontaneous lovers »» Will Halstead 🚑
Honeymoon »» Jay Halstead 🚓
Breakup »» Conner Rhodes 🚑
Bundle of joy »» Jay Halstead 🚓
The perfect day »» Ethan Choi 🚑
There for you »» Kelly Severide 🚒
Captured »» Antonio Dawson 🚓
Your guy best friend he's slightly jealous of
I love you »» Will Halstead 🚑
A sad call »» Matt Casey 🚒
Someone else »» Connor Rhodes 🚑
The Challenge »» Jay Halstead 🚓
Never coming back »» Ethan Choi 🚑
Hangover »» Will Halstead 🚑
In the rain »» Kelly Severide 🚒
Stuck at work »» Jay Halstead 🚓
Bad Luck »» Matt Casey 🚒
Last Day »» Connor Rhodes 🚑
Tired »» Will Halstead 🚑
Sick »» Ethan Choi 🚑
Ghost »» Jay Halstead 🚓
Accident »» Kelly Severide 🚒
Birthday »» Matt Casey 🚒
Platonic Soulmates » » Conner Rhodes 🚑
Friends to Lovers »» Will Halstead 🚑
Four Years »» Ethan Choi 🚑
Late Night Anxiety »» Jay Halstead 🚓
Time Together »» Matt Casey 🚒
Before You »» Kelly Severide
Hard To Love »» Will Halstead
No Power »» Jay Halstead
Two Broken Legs »» Connor Rhodes
First Date »» Ethan Choi
Empty Room »» Matt Casey
Falling in love »» Kelly Severide
Mine »» Will Halstead
Apart of the job »» Jay Halstead
Happy Surprise »» Conner Rhodes
I love you »» Ethan Choi
Moving on »» Kelly Severide
Wedding Day »» Matt Casey
A Break »» Jay Halstead
Road Trip »» Will Halstead
Beautiful »» Conner Rhodes
Secrets »» Ethan Choi
Forever together »» Kelly Severide
A baby »» Matt Casey
Enemies to lovers »» Jay Halstead
Sick Days »» Will Halstead

The Halstead sister »» Matt Casey 🚒

3.6K 56 3
By SuperWinchester1967

Word count; 789

The sound of teeth chattering could be heard from a mile away. Matt and I are waiting outside in the cold Chicago winter air for my brothers, Will and Jay Halstead to arrive. Matt and I have been dating for six months and if my brothers knew then they wouldn't be too happy.

They have always been overprotective of me considering I am their younger sister. Every guy in my life never lasted longer than a year because of them. But something tells me Matt is different. We have been working together at firehouse 51 for nearly six years.

It's only now that we started to make our relationship official. My brothers are confused as to why I've asked them to meet me for dinner. As soon as they approached us frowns formed on their faces. "What is this?" Jay asks, his eyebrow quirked up in suspension.

"Can we please just go inside first?" I ask my annoying yet sweet brothers. They nod and we go inside where a nice waitress seats us. They wait for me to talk after getting our drink orders.

"Why are we here?" Will frowned.

"Well there's something I need to tell you guys but please hear me out..." I glanced at Matt and he rested his hand on my back. "We're dating." I blurt out. Their eyes widen and they look between each other then back at us. The waitress came back with our drinks before leaving again.

"Hell no!" Jay glared.

"Y/n no offense but none of your previous relationships ever panned out." Will gave me a worried look. Instead of getting angry I took in a breath to calm down.

"That's because you guys never give them a chance. It's different with Matt. He's kind, compassionate, and he cares about me."

"Yes and y/n is special and makes me feel ways I've never dreamt possible." Matt added.

"Your ridiculous if you think we'd ever let you two go out! Y/n he's only going to hurt you." Jay started to raise his voice. This time I got angry.

"You guys are being unfair. Will I supported you and Natalie even after you proposed to her then had to break it off. And Jay I have supported you and Hailey together since the beginning. So why is it so hard for you guys to give Matt a chance?"

The glare on Jay's face never falters but Will's eyes softened and he let out a sigh. "She's right you know," he looked over at our angry brother Jay. "She has always supported us no matter what and we tend to get hypocritical about every guy she's ever liked," he admitted.

"Yeah but she's y/n. I swore when mom and dad died that I'd protect her no matter what." Jay defended.

"And I love you for it but heartbreak and pain, it's all apart of life. To be honest with you I wouldn't want to go through life without it. You need to let me experience these things for myself." I tell him. He gave me a worried look then looked over at Matt. Finally he sighs and nods his head yes.

"Fine...okay. But listen and listen good. I'm a detective so if you do anything and I mean anything to hurt her I can make you disappear like that," Jay said as he snaps his fingers. I glare at him and he ignored me.

"Okay that's enough of that, let's order some food please." Will said. Tonight is going to be interesting to say the least. We got through the night without any problems even though Jay kept giving Matt a pointed look. He will come around eventually, he's just a very overprotective big brother.

When the night ended I hugged my brothers and said goodbye to them before letting Matt take me home. "Should I be scared of Jay or..." he said as we got to my door. I laugh and wrap my arms around him.

"No there's nothing to worry about. He will come around but just needs some time. I promise."

He smiles and ends the night by kissing my lips softly. Once saying Goodnight I went inside and started getting ready for bed. Just as I'm about to crawl under the covers my phone dings with a text followed with another one right after. I read the first one which is from Jay saying "did he hurt you yet?" And the other one is from Will saying "don't worry I've got Jay under control"

It made me smile and reply back to them before going to sleep happily. As annoying as they are, I can't help but love my two older brothers.

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