Okay, so I think Dean, Castiel, and Jack broke me the most... Good luck!
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D E A N
• You learning to forget what you're missing and appreciating what's remaining. After many nights of feeling rejected by, whom you believed was the love of your life, you slowly learned how to move on. However, you still enjoy the small things. You still enjoyed his laughter. His smile. His hugs. You still cherished moments with Dean, but you learned to accept that it wasn't meant to be.
• Looking forward to the future and deciding to focus on yourself for a while.
• You and Dean remaining great friends.
• Still hunting with the Winchesters whenever you got the chance.
• Missing him a lot when he is gone, but having the strength not to get hung up on him.
• Letting him go.
• Meeting someone else during a midnight hunt. Him/Her saving your ass when things get a little out of hand, but of course, you don't like to admit when you are beaten. So you and him/her don't get along very well at first, but you just can't help but be around each other ever since that night.
• "I had it covered!"
• "Sure, you did."
• Him/Her taking the time to get to know you. The real you. The you that's afraid to let people in because of your fears of being rejected again. Them just being incredibly patient with you because to them you were worth every second!
• "I'm sorry. I'm just afraid."
• "Don't be afraid, Y/N. I love you and no one is going to change that."
• Introducing him/her to the Winchesters. There is an awkwardness beyond belief in the first few hours, but then Sam is able to break the tension with a hunt. You decide to tackle it together. This allows the boys to get to know your new love interest a little bit more.
• Dean not realizing what he threw away until he sees you in another person's arms.
• Each time he sees the two of you together, another piece of his heart breaks.
• Hating himself for not realizing what he had until it was gone. He misses you like crazy and usually spends his time without you trying to drink his pain away.
• "Dude, you're the one that let her go in the first place."
• "You don't think I know that, Sammy. I thought I didn't love her like that, but now, I know I do."
• "She's with someone else now, Dean. And if you can't tell she's happy. Don't you dare ruin it for her."
• Him not listing to Sam's advice because as soon as Sam and your new boyfriend/girlfriend leave, he confesses his feelings. He didn't really know what he was thinking... Maybe you would consider his offer or maybe you would just run into his arms. He wished it was any of those options because he wasn't prepared for your angry tears.
• "I'm so sorry. I just—I don't know—what I was thinking that night. I just know now that I love you. That I've—I've always loved you."
• "No, Dean! You don't get to do this to me again. You don't get to stand there and tell me you love me and expect me to fall right into your arms. That's not how it works. I've moved on."
• Walking away from him for good after that.
S A M
• Feeling a lot of pain when letting him go, but knowing it would hurt more if you continued to hold on.
• Still keeping in touch with him, making sure he's taking care of himself. Being his best friend and his best supporter because it's what you're meant to do.
• Thinking about him from time to time, but not letting your previous feelings control your life.
• Getting back out there and having fun!
• Sam being your hardest goodbye, but that cute bartender you had the courage to hit on and give your number to one night being your easiest hello!
• "Hi, what can I get you?"
• "A bottle of beer and maybe a shot of you."
• "Cheesy, but maybe you'll get lucky."
• Slowly opening up to them as time goes on. Your months filled with movie dates and Take-Out Tuesdays when you both get off work. Laughter, hugs, smiles, cheesy pick up lines and puns, stupid pictures on your phones, and a lot of sweet kisses under the moonlight. Just taking time to fall in love with each other.
• Him/Her making you feel normal again like you were never really hurt in the first place.
• "I think I'm falling in love again."
• "I think I'm falling in love with you too."
• Bumping into Sam again and being surprised that your old feelings were completely gone. He didn't hold any power over you anymore and that was the most freeing feeling.
• Him being happy to see you, but then becoming strangely quiet when he notices the ring on your figure. You explain that you've been engaged for a few months now, but it only makes the situation feel weirdly awkward. Despite this, you invite him to dinner so that he can meet your fiancé.
• The dinner going rather smoothly, but you can't help but feel the tension brewing between you and Sam when it's over. You wanting to ask what was wrong, but you let it go instead.
• Sam returning to Dean after dinner with the pure intention of getting drunk. Of course, Dean is more than welcome to join him.
• Waking up the next morning a complete mess. Hair in knots, dried throw up on his shirt, and eyes bloodshot from crying.
• "Whoa! Dude, you look awful!"
• "I think I'm in love."
• "Wait. Are you having a stroke? Do you smell burnt toast?"
• Him realizing how much he actually missed you after seeing you so happy at dinner.
• He doesn't know why, but he can't shake the feeling that he's being replaced. He knows he shouldn't be feeling this way because he's the one that had no interest in you in the first place, but damn it, he can't get you out of his head.
• Deciding to tell you, even though he knows how you're going to react and is pretty sure it's a really bad idea. But love makes you do stupid things... And he was about to do the stupidest thing ever.
• Him waiting for your fiancé to leave for work so he can get you alone. He confesses his feelings while bursting into your apartment.
• "Hey, Y/N! I don't mean to be barging in like this, but I have to tell you something."
• "Um—Okay?"
• "I'm—Y/N—I'm."
• "What?"
• "I'm in love with you. I'm sorry I didn't realize sooner and I'm sorry if I'm overstepping. But, I just—I just needed to say it."
• You surprisingly not getting angry. Letting him down gently, because you choose to take the high road.
• "I'm sorry, Sam. I loved you and a piece of me will always love you, but I've finally found happiness somewhere else. I've moved on. So, it's time for whatever we had or could have had to end."
• Regardless of his heartbreak, he understands and respects your wishes. You don't see or hear from him again after that.
C A S T I E L
• The best lesson you come to learn about humanity is that the act of letting something you love go is one of the most freeing moments you can ever experience because that's when you realize you can't change what isn't meant to be.
• Not having Castiel by your side being very hard, but with every second, minute, hour, day, and month that passes, you are able to take one step closer to your new purpose in life.
• Leaving with no strings attached. There's no contact between you and Castiel for a while. The two of you are completely separated from each other's lives.
• Being on your own for a little while and learning how to live independently.
• Running into your next crush accidentally. However, the human that you find yourself bumping into doesn't just agreed to stay, but becomes a major part of your life.
• "I'm sorry, I wasn't looking."
• "That's okay, a beautiful person like you is worth stopping for."
• Them making you feel human just like Castiel, but this time it's in all the right ways.
• Having that romance you always saw in movies.
• Finally getting to feel what it's like to have someone love you back!
• You being really happy that they are able to accept that you are an angel because you really were insecure and afraid to tell them. Them passing out the first time you showed them your wings, but they learned to love them just as much as they loved you.
• "I don't care that you're an angel. I care about you. It's the person inside the vessel that I love. Not your body."
• "I never thought I would be able to love again."
• Meeting up with the Winchester boys after hearing Sam's urgent prayer. It was about Castiel and even though you weren't planning to go, your other half told you to. He/She always being understanding and trusting because they know you can't ignore a call for help.
• You taking care of Castiel after he gets hurt during a hunt. The two of you reconnecting like nothing ever happened. This causes you to stay a few more days than planned and you start to get worrying calls and messages from your lover back home. As much as you want to go back to them, something manages to keep you in the bunker.
• Old feelings resurfacing, making you feel conflicted. It gets even worse when your boyfriend/girlfriend shows up, interrupting a dinner you and boys planned.
• Having to sit through a very awkward car ride home after introducing them to your boyfriend/girlfriend.
• Castiel not knowing how to control his emotions when he sees the two of you together. He feels anger, causing him to send a death glare your boyfriend's/girlfriend's way. But, then he feels sad because he believes that it should be him that you're hugging and kissing instead.
• Him bitterly realizing that he had his chance with you, but didn't take it.
• Sometimes he hates seeing that you're so happy with them. Other times he's thrilled that you had found someone that loved you, even though he wishes it was him that you were holding.
• "Um. Cas. If you stare at them any harder, you're going to drill holes."
• "I'm an idiot for letting her go, Dean."
• "I'm not going to disagree with you."
• Even though he knows it's wrong, he decides to confess his feelings to you. After you convince your boyfriend/girlfriend to leave, promising them that you would return, Castiel makes his move. He doesn't care about the outcome or how he's probably going to regret doing this come morning. All he knows is that he loves you. He loves you so damn much that he will never forgive himself for rejecting and hurting you all those months ago. He's fully prepared to lay his heart out for you, just you had once before, only this time he's at the receiving end and about to feel your pain.
• The moment you lay eyes on him, you know what's coming.
• "Cas, please. Please don't do this."
• "I have to because if I don't it'll kill me."
• Him whipping your tears, and you allowing him to.
• "I love you."
• His words sounding so genuine. It feeling like everything you dreamt it would be. It looking just the way you pictured it. It being exactly the way you wanted it. Yet, it breaks your heart because you know right that then and there that your heart belongs to other. You don't feel the same way about him anymore, but it still hurts to see his reaction because he knows it too.
• "I'm sorry, but I belong with them."
• "Then I'm happy for you."
• Him losing faith in love because he knows he's just lost his only chance at ever having it.
G A B R I E L
• Realizing that if you let go, forgive yourself, forgive the situation, and understand that the situation is over, you can move forward with the rest of your life.
• Forgetting is the best medicine.
• Cutting all ties with your previous life and moving away to start over.
• Paying a little bit more attention to the smaller things in life. Focusing not so much on yourself and deciding to put others before yourself. Volunteering for your local community shelter. There you learn to not only distract yourself but to leave things in your past.
• At times feeling like giving up on love, but then when you least expected it, someone new waltzes into your life and takes your breath away.
• Meeting them while working on an event for your community's local charity. They agreed to help you plan the ceremony and during that time you start to grow a very strong bound.
• "Need some help?"
• "That would be great, thanks!"
• Becoming great friends before they had the courage to ask you out. To be honest, it took you equally as a long to have the courage to say yes.
• A lot of playing in the snow together during the winter, going to plays during the summer, working alongside each other each day, movie marathon with ice cream sundaes every Saturday night, empty Chinese containers and pizza boxes laying around the apartment, and of course late night hot chocolate run whenever you ask for it!
• Reaching that point where you don't even think about Gabriel anymore and at the slight chance that you do, all of your feeling disappear.
• Somewhere between all the laughs, long talks, stupid little fights, and all the jokes the two of you fell in love.
• "I love you so much."
• "Oh, don't be such a sap."
• "If that's your way of saying I love you too, then we're going to have to work on that."
• Gabriel coming back to you once he realizes that he misses you and really does want to be with you.
• Him feeling jealous when he sees that you have moved on and found someone else to care for.
• Him being disappointed in himself because he knew he had the opportunity to be with you but he decided to let you go instead. Now he was back and he knew that was unfair, but he can't make the feeling go away.
• Although he knows that you are happy and have found someone else, he needs to know if he still has a chance.
• Him showing up at your door to confess his feelings.
• "Hi, Y/N."
• "Gabriel?"
• "Yeah, it's me."
• "What are you doing here?"
• "I came to tell you that I'm sorry I left so suddenly, but I just didn't know how to tell you. Tell you—that I—I love you."
• You being shocked not only by his confession but also by the fact that you don't feel the same way as you did before.
• "I love someone else, Gabriel. I'm sorry. I wish you the best."
• Him only being a part of your past after that.
• Never seeing him again.
L U C I F E R
• Learning to move on while also realizing that it's not about forgetting all the good times, it's about you having to accept all the bad with the good and continue living.
• Getting yourself out of the toxic relationship you had created with him.
• Him letting you go, even though his selfishness wants to keep you close.
• Miscommunication killing your friendship.
• Your past being the number one reason you have a hard time when moving on. However, you managed to pillage through and find new happiness elsewhere.
• Slowly starting to believe in yourself and others again.
• Throwing yourself into your hobbies and passions. During this time, your dream of finding love again takes a back seat.
• Sweet memories of him filling your loneliest days, but it doesn't hurt like it used to. It's more like a coping mechanism.
• When you finally feel like you're over him, that's when someone else walks into your life.
• Meeting someone new while taking a trip to visit your daughter's grave.
• Instantly connecting because of your shared experience of losing a child.
• "Cancer."
• "Car accident."
• Falling for each other at a steady pace because you've both been hurt before.
• Them having the power to make you feel something you hadn't felt in a long time. You slowly begin to figure out that that feeling is love. It's the best type of love too because it's not one-sided, but mutual between the two of you.
• Realizing that falling in love with someone and having feelings for someone are two completely different things. You know this now because what you felt for Lucifer is nothing compared to the way you love him/her.
• When you are with them, you are no longer afraid of falling in love.
• "You make me want to love again."
• Lucifer finding out about your new relationship and becoming oddly quiet about the whole thing.
• His possessiveness building up over time.
• Him having to watch the two of you together and hating every minute of it because he secretly wants to be by your side.
• Despising himself because he knows you gave him so many chances before and he didn't take any of them because he was too much of coward to realize that he truly loved you.
• Knowing the realization hits him too late, but that doesn't stop him from going to you and confessing his love for you. He knows it's wrong, but he's never been one to do the right thing and he isn't about to start now. Especially since it's you that's at stake. He can't lose you again, even though he knows he already has.
• "Lucifer, I can't do this right now."
• Him not having to say anything because you always know what he is thinking.
• "I just wanted you to know that I love you."
• "No. You can't--"
• "I know. Just look me in the eye and tell me you don't feel the same. If you're not lying, I'll never bother you again. I just need to know."
• You doing exactly that and being forced to watch his heartbreak as he finally begins to accept that he can't have you now.
• It hurts, but there's also a sense of relief that flows through you. You never knew you held the strength to stick up for yourself and to walk away from a negative relationship.
• Him keeping his word and never coming back to you again.
B A L T H A Z A R
• Even when everything seems to be going wrong in your life, you learn to stay positive.
• Giving up hunting for a while to focus on yourself and what you really want in life.
• Deciding to forget about the supernatural and to lead a normal life for once.
• The transition being oddly easy. However, you did have your difficulties with sleeping through the night without having Balthazar by your side.
• Your relationship with him taking a quiet turn for the better.
• Moving on and letting go.
• Taking your time for once.
• Building friendships within your community and working that nine to five job, but still getting drunk whenever you can. And during one of those late nights, you meet your next chapter in life.
• Long talks at the bar together and midnight drinking.
• Opening up to each other and realizing that you're both ready to jump head first into love again.
• Them making you feel happy. A feeling you haven't felt in a long time.
• "I don't deserve you."
• "Yes, you do. You deserve the world."
• Not returning to the hunting life after meeting them.
• Getting married and starting a family.
• During all this time, you never realizing that Balthazar had been watching over you. Within a few weeks of seeing you two together, he felt happy for you, but as time went on jealousy started to kick in.
• Him realizing that he loves you, but he knows it's way too late for a confession.
• "You do deserve the world, Y/N. I'm so sorry I didn't realize it sooner."
• Though the pain never goes away, he continues to watch over you and your family. Protecting them for as long as he lives.
A D A M
• Understanding that the key to moving on is that you must understand why you felt what you did and why you no longer need to feel it. Only then can you move on.
• Letting go of both your ex-boyfriend and Adam.
• Crying all your tears out for the last time to the sound of loud and weirdly relatable music. From that point on, never spilling tears in his name again.
• Over time realizing that you don't really miss him, you miss the feeling he provided for you. Once you understand that, moving on became a lot easier.
• Quitting your search for love and taking the time to learn to love yourself.
• Along the way, someone else starts to fall in love with you as well.
• When you're finally ready to start dating again, you don't have to look very far because the love of your life is standing right in front of you.
• Them confessing their feelings to you. At first, you were a little hesitant, but once they began to show how much they really did care, you fall right into them.
• "Thank you for making me see that I'm worth something."
• "You're worth everything, Y/N!"
• Adam making his way back into your life, but you keep him at a safe distance.
• Him realizing that the more you push him away, the more he misses you and wants to be with you.
• You telling him, before he can even say anything, that it's too late and that you have moved on.
• "I found a new love and one day I hope you find the same."
• You leaving him to regret all of his mistakes.
• Him losing not only a true friend but a true love as well.
C H A R L I E
• Accepting the fact that you're not meant to be together and trying your best to move on.
• Being in a complete daze for weeks, but Netflix and Hulu are able to help you through most of your loneliest days.
• Continuing to be Charlie wingman/wingwomen.
• You always cheering her on but also learning to cheer yourself on.
• Finally realizing that it's not the end of the world, but the beginning of a new adventure!
• Going to Comic-Con for the first time without her, but also finding someone new along the way.
• They were cosplaying as Sherlock Holmes and you as John Watsons.
• Instantly hitting it off!
• Them allowing you to forget your feelings about Charlie so you can create new ones.
• Truly finding your better half!
• "I love you."
• "I've always assumed that love is a dangerous disadvantage."
• "Did you just..."
• "Oh my god, Y/N! Of course, I love you too!"
• Charlie realizing the moment she meets them that she made a big mistake. Despite this, she doesn't interfere because seeing you happy is worth all the pain.
• You hearing her confession in secret, but having the strength to walk away.
• "I've always loved you, Y/N. I'm sorry it took me so long to realize."
• Still the best of friends!
J A C K
• Constantly trying to find someone new in all the wrong places. This leads you into a few toxic relationships that weren't exactly good for you, but they made you feel somewhat wanted. Ultimately, you force yourself down a dark path in your search for acceptance.
• Pushing everyone away because you don't want to be a bother to anyone. This includes your brothers, Castiel, and of course Jack.
• Through the breaks in your sadness and self-loathing, you still manage to share good memories with Jack. You still remain friends, even though you know it's not helping you move on.
• Your bedroom door becoming a revolving door for a lot of random boys during lonely nights.
• Treating yourself like you're worthless because that's how you believe people you care about see you. You don't believe you're worthy enough to be loved because everyone you give your heart to rejects it.
• Your teenage angst combining perfectly with your new love interest's easygoing and bubbly personality. The two of you are like oil and water, but for some reason, you attract to each other like magnets.
• You meeting them after they decide to help your brother's with a case. The boys bring them back to the bunker where they are introduced to you. At first, you want nothing to do with them, but as time continues you find yourself becoming interested in them.
• Them take a liking to you almost instantly. He/She trying patiently to get you to open up. They never give up on you, even when you try to push them away.
• You realizing that they aren't going to go anywhere and finally deciding to humor them.
•Though you try to convince yourself that it's only going to be a quick conversation, it turns into a night long chat. From that point forward, it was hard not to talk to them.
• Them being able to relate and understand you better than the four men you've known practically her whole life.
• You falling for them, but still terrified to tell them because of what happened the last time. However, you do it anyway because the past few months with them have thought you that there is no better time than the present.
• "I have to tell you something."
• "Yes, Y/N?"
• "I love you."
• "I love you too."
• Being misunderstood together.
• Them making you realize that your life is worth fighting for.
• Jack noticing your interest in the new hunter and feeling things that he can't quite explain. Things like his sudden agitation towards him/her whenever he/she is around you or the feeling of his heart skipping beats when you look at them the way you used to look at him.
• Jack absolutely despising them, but not knowing why.
• Him deciding to talk to Dean about it.
• "Why do I get so mad when I see them together?"
• "That's jealousy, Jack."
• "Oh."
• Him finally realizing what you meant when you said you loved him all those times before. His realization making him feel stupid because the second he replays the scene in his mind, he begins to feel the same way about you.
• Despite Sam and Dean's warnings, Jack decides to talk to you about it because he feels like he's going to have even more regret if he doesn't tell you.
• "Y/N."
• "Yeah, Jack?"
• "I love you."
• The words sting because you don't realize that he's actually confessing his feelings at first, and not just saying it in a friendly way like he always does.
• "I love you too. You will always be my best friend."
• "No, Y/N. That's not what I mean. I'm—I'm in love with you."
• Your heart breaking because you don't feel the way you thought you would feel when he did say those three little words to you.
• Knowing then that your heart belongs to another.
• "I'm sorry, Jack. But, I don't love you like that anymore."
• Him having to pretend that he's happy for you for the rest of his life.
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A/N
I know, not my best! But damn some of it hit a little too close to home...