Dating Sam Winchester

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General Headcanons



Intellectual Conversations: Sam loves engaging in deep and meaningful conversations, ranging from philosophy to mythology. You often find yourselves lost in discussion late into the night.
Book Recommendations: Sam frequently recommends books he thinks you'll enjoy and loves discussing them with you after you've read them.
Protective Nature: He is very protective of you, always ensuring you're safe and secure, both physically and emotionally.
Cooking Together: Sam enjoys cooking and loves spending time in the kitchen with you, trying out new recipes and enjoying the process together.
Workout Partner: Sam is dedicated to staying in shape and enjoys having you as his workout partner, motivating each other and sharing a post-workout smoothie.
Research Buddy: He appreciates your help in researching for hunts, and you both make a great team when it comes to digging up information.
Camping Trips: Sam loves nature and often takes you on camping trips where you can both unwind and enjoy each other's company away from the chaos of hunting.
Soft and Affectionate: Despite his tough exterior, Sam is incredibly affectionate in private, always making sure you feel loved and cherished.
Coffee Dates: Sam enjoys simple pleasures like having coffee with you, whether it's at a cozy café or a quiet morning at home.
Supportive Partner: He is always there to support your dreams and goals, encouraging you to pursue what makes you happy.


Specific Scenarios 
Hunt Gone Wrong: After a particularly rough hunt where you got injured, Sam is overly attentive, fussing over you and making sure you're comfortable and healing properly.
Birthday Surprise: Sam goes all out for your birthday, planning a surprise that includes your favorite activities, a homemade cake, and a heartfelt gift that shows how well he knows you.
Stress Relief: After a stressful week, Sam plans a relaxing evening for you, complete with a warm bath, your favorite movie, and a massage to help you unwind.
First I Love You: The first time Sam says "I love you" is during a quiet moment, maybe while stargazing on one of your camping trips, making it a perfect, intimate memory.
Jealous Sam: When someone flirts with you at a bar, Sam's protective side comes out. He isn't aggressive, but he makes it clear that you're with him through subtle, possessive gestures.
Library Date: Knowing your love for books, Sam takes you on a date to a massive, beautiful library, where you both spend hours exploring and sharing your favorite finds.
Comfort During Nightmares: When you have nightmares, Sam is always there to comfort you, holding you close and whispering soothing words until you fall back asleep.
Holiday Traditions: Sam loves creating new holiday traditions with you, from decorating the tree to baking cookies together, making the season special despite their often hectic lives.
Road Trip Adventures: On a rare break from hunting, Sam surprises you with a spontaneous road trip to a destination you've always wanted to visit, creating wonderful memories along the way.
Helping You Study: If you're studying for an important exam or working on a big project, Sam helps you stay focused and organized, providing snacks, coffee, and encouragement throughout.
Music and Memories: Sam shares his favorite music with you, and you both create playlists that remind you of your time together, each song holding a special memory.
Late-Night Talks: Sometimes, after a long day, you both stay up late just talking about everything and nothing, cherishing the quiet, intimate moments together.

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