(Incandescent)...Multifandom Imagines

Dating Dean Winchester

General Headcanons 

Protective Nature: Dean is incredibly protective, always making sure you're safe and well.
Cooking Together: He enjoys making burgers and pie with you in the kitchen, playfully teasing you while cooking.
Classic Rock: Car rides are filled with classic rock, and he loves singing along with you.
Hunting Knowledge: He teaches you basic hunting skills, even if you're not involved in hunts.
Quality Time: Enjoys spending quiet evenings watching old movies or binge-watching TV shows.
Gifts: Brings you small, thoughtful gifts from his hunts or road trips.
Emotional Support: Despite his tough exterior, Dean is always there to listen and provide emotional support.
Teasing: Playful teasing and banter are a regular part of your relationship.
Nickname: He has a special nickname for you that only he uses.
Shared Responsibility: Dean insists on sharing responsibilities, from chores to big decisions.
Garage Hangouts: Enjoys working on the Impala while you keep him company, sometimes teaching you a thing or two about cars.
Supernatural Protection: Keeps wards and protective symbols around your home to keep you safe.

Specific Scenarios
Road Trip Adventures: You and Dean take spontaneous road trips in the Impala, exploring new places and finding hidden diners with the best pie.
Rescue Missions: There are times when Dean has to rescue you from supernatural threats, showcasing his bravery and dedication.
Celebrating Wins: After a successful hunt, you two celebrate with a night out or a special homemade dinner.
Comfort After Nightmares: Dean comforts you after nightmares, holding you close and whispering that everything will be alright.
Meeting the Family: He introduces you to Sam and Castiel, and you become part of their close-knit family.
Research Nights: Spend evenings researching supernatural lore together, with Dean making it fun and engaging.
Training Sessions: Dean sets up training sessions to teach you self-defense and how to handle different supernatural creatures.
Surprise Dates: He surprises you with impromptu dates, like a picnic under the stars or a visit to a secluded lake.
Dealing with Injuries: Tending to each other's wounds after hunts, with Dean always trying to make light of the situation to keep you calm.
Anniversary Traditions: Dean creates unique traditions for your anniversaries, like visiting a specific spot or rewatching a favorite movie.
Pranks and Jokes: Light-hearted pranks and jokes are a staple, always ending with laughter and playful retaliation.
Holiday Celebrations: Dean goes all out for holidays, ensuring you have memorable and special times together.
Handling His Past: You help Dean cope with his past traumas and losses, providing a safe space for him to open up.
Dealing with Demons: Sometimes you have to deal with demon-related issues, with Dean always prioritizing your safety and well-being.
Late-Night Conversations: Deep late-night conversations about life, fears, and dreams, often leading to a stronger bond.
Singing Together: Occasionally, you catch Dean singing your favorite song when he thinks you're not listening, and it always makes your day.
Impromptu Dances: Dean pulls you into impromptu slow dances, often in the most unexpected places, like the garage or the kitchen.