daiken headcanons

Below are my main daiken headcanons, though quite of bit of this is also included in my timeline.

daisuke

Birthday: August 8th, 1991
Sign: Leo (sun), Cancer (moon), Aries (rising)
MBTI: ESFP
Top Love Language(s): physical touch & acts of service
Sexuality: (disaster) bisexual, male leaning
Other Details: ADHD, low self-esteem, ambidextrous (but doesn't realize that's rare)

Crest of Miracles
V-mon > XV-mon > (non-gold) Magnamon > UlforceV-dramon

ken

Birthday: July 16th, 1991
Sign: Cancer (sun), Virgo (moon), Scorpio (rising)
MBTI: INFJ
Top Love Language(s): quality time & physical touch
Sexuality: gay/demisexual
Other Details: depression, anxiety, PTSD, chronic nightmares

Crest of Kindness
Wormmon > Stingmon > Jewelbeemon > BanchoStingmon

ken's history

The Ichijoujis lived at Hikarigaoka in summer 1995, and Ken saw the Greymon/Parrotmon fight. This is why Ken has a Crest.

I have a full headcanon timeline for Ken here.

school life, friends & dating life

Daisuke has no real friends before 02, and that's why he latches onto Hikari and Taichi.
Ken's only real friend before 02 was Ryou, who he had a crush on, but Ken thinks that Ryou was his imaginary friend because he only saw him in the Digital World and then he just disappeared. Everyone at school is intimidated by him or thinks he's useless now that he's no longer a genius.
All the girls adore Ken because of how quiet and gentle and pretty he is, and he gets a lot of Valentine's chocolates because of it, but he never reciprocates the affection.
Daisuke isn't very popular with girls, and he's completely oblivious with a guy or girl has a crush on him, even when they outright flirt with or confess to him. He tends to complain about how hopeless trying to find a girlfriend is - and then immediately flirt with his best friend without realizing it and sending Ken into a gay panic spiral.

sleepovers & family interactions

Daisuke hears Ken laugh for the first time during their first sleepover in episode #35, and he is determined to make Ken laugh as much as he can.
They have sleepovers almost every weekend, switching off between whose home they go to. Daisuke prefers Ken's apartment, but Ken prefers Daisuke's.
Mr. and Mrs. Ichijouji adore Daisuke and basically adopt him. Mrs. Ichijouji makes sure they have lots of extra food when he's there for dinner because he and V-mon eat so much. He helps in the kitchen.
Ken enjoys the loud, energetic atmosphere at Daisuke's home, but he sometimes gets uncomfortable when Daisuke and Jun fight because it reminds him of his struggles with Osamu. He's comforted by the fact that Jun loves Daisuke very much despite their fights and how annoying she finds him.
When they can't spend time together in person, they email constrantly and talk on the phone every night before bed. Daisuke's mom gets mad at him for taking the cordless phone to his bedroom and often falling asleep without putting it back in the kitchen, but he cannot imagine going to sleep without hearing Ken's voice first.

mental health

Ken struggles with depression, anxiety, and general PTSD. It improves, but his mental health has ups and downs, and because of this, his self-care regimen is very important to him.
He is able to compartmentalize and push aside his mental and emotional issues when they have an important mission, often in complete disregard for his own mental health.
Ken is scared of water/the ocean and doesn't know how to swim.
Ken has nightmares regularly. Many of them are about drowning and/or the Dark Ocean.
Ken isn't comfortable playing video games for a long time. It takes a great deal of effort for him to try again. While Daisuke likes all kinds of games and is partial to fighting games, Ken prefers puzzles and co-op instead of competitive games
Ken starts going to the onsen not long after 02, and it becomes part of his self-care regimen like his daily morning runs. Ken never mentions his love of the onsen to the group until the Kizuna audio drama because he's nervous to be that physically open and vulnerable around Daisuke.
Ken hates being recognized and feels comfortable with his fame. Sometimes, he even has panic attacks because of it.
Daisuke, on the other hand, enjoys being recognized as a Chosen Child but is super humble and always plays down his role and plays up everyone else.

As much as I love 02's theme of "moving forward," that isn't going to stop all these kids from having PTSD after All The Trauma they endure, and Ken experiences more trauma than any of the other Chosen Children.

what if tri. were good

Ken is comatose for a while (somewhere between a couple weeks and a couple months) since he is without oxygen for several minutes and Yggdrasil's Dark Gennai steals his energy/life force every time he impersonates him. Ken is the last of the 02 kids to wake up and leave the hospital. Daisuke only leaves his side when he's forced to.
Daisuke blames himself for their defeat, especially for not contacting Hikari, Takeru, and the others for help, and he gives Taichi his goggles back because he feels unworthy wearing them. He doesn't get out of this funk until Ken wakes up and knocks some sense into him.
Taichi doesn't give Daisuke the goggles back until after Kizuna when he feels he doesn't need them anymore.

Okikage's fic about Ken being in a coma is utter perfection & I basically wrote a fic of my Daisuke dealing with tri. trauma headcanon here.

careers & adulthood

Ken studies psychology in college because he wants to understand himself better and to help kids like him who feel scared and alone. Mental health care isn't in high regard in Japan, so he becomes a teacher, which is basically the closest thing Japan has to a child therapist.
Ken works as the same elementary school as Hikari, and they're close friends. She works with kindergarteners, but he works with older kids.
Daisuke strives to be the world's best ramen maker. He starts off with little finesse, but he has good instincts and his determination leads him closer and closer to his goal.
Ken always wants to be the first one to taste his recipes. Daisuke appreciates his kind but honest critiques.
Daisuke learns the important of having a clean cooking space, and he's adamant about keeping the kitchen spotless. In contrast, Ken is especially messy in the kitchen, and Daisuke often takes over to salvage his attempts to cook.
Daisuke tries to teach Ken how to cook, but it takes a lot of time and effort for Ken to learn even the simplest recipe.
Daisuke's ramen cart business takes off worldwide and makes him a bunch of money, but Daisuke has no interest in running a business empire. He still runs on of his carts/shops with V-mon, preferably the one closest to Ken's school. He often makes Ken bento boxes to take to school for lunch.
Ken doesn't need to work with how well Daisuke's business is going, but he loves his job and would go crazy if he didn't have a reliable schedule/routine. He enjoys Daisuke taking care of him, both financially and on a day-to-day basis, but he feels guilty and ashamed for relying on him.

I wrote a fic about how I envision their life as adults here, though it has Ken as a high school teacher instead of an elementary teacher, mostly because that was easier to write, and probably isn't super Japan-accurate since it's one of my earliest fics and I hadn't done a whole lot of research yet.

getting together

Daisuke crushes on Ken before learning he's the Kaiser, and that crush comes back the moment he touches the golden Digimental. His feelings are immediate and strong, but he doesn't understand they're romantic until much later.
Ken's feelings develop much more slowly. There are hints early on, but he is unable to accept them and specifically distances himself from Daisuke by calling him by his family name. He is in denial of his feelings for a long time and is prone to gay-panicking when Daisuke gets too close, physically or emotionally.
They constantly find ways to be physically close and don't even consider that sharing food and holding hands, etc., isn't typical "best friend" behavior.
They finds comfort in feeling and hearing each other's heartbeats. Ken uses Daisuke's steady heartbeat as a way to soothe himself, and their heartbeats synchronize when they're physically close.
During sleepovers, they sleep in the same bed, and Ken almost never has nightmares when they share the bed.
Ken finds Daisuke's impulsive tendencies endearing and usually goes along with his ideas without a second thought, no matter how silly or stupid or fucking gay they are. He finds it difficult to resist agreeing and struggles to say no even when he knows it's a bad idea.
Daisuke is super possessive of Ken and gets self-conscious and insecure when Ken has other friends, especially if it's not one of the Chosen. This childish jealousy is made more pronounced after he realizes his romantic feelings.
Nothing really changes about their relationship dynamic once they start dating. The only real change is how they physically show and share their affection.

developing sexuality

Daisuke is naturally a highly sexual person. The first time he touches himself is the night after he and Ken first Jogress-evolve, and he begins regularly masturbating by the end of 02. He usually masturbates before bed because it helps him fall asleep, but he will fit it in whenever he can.
Daisuke discovers porn not long after and really likes looking at both guys and girls, but he honestly doesn't need any extra masturbatory fodder because he's basically always on the verge of being aroused.
Ken is repressed and rarely masturbates. It makes him uncomfortable and ashamed.
Ken tries to think about girls because he's in complete denial that he's gay, but he somehow always winds up thinking about Daisuke, no matter how much he tries not to.
Even after he becomes more comfortable with his sexuality, Ken doesn't really see the point in masturbating. He'd rather get get off with a partner (read: Daisuke) than by himself.
Ken's porn is BL manga and novels, which give him the emotional aspect he needs to get truly turned on.
Lots of Ken's nightmares include monsters of his past non-conning him, and he wakes up with a boner or just having orgasmed. He is very ashamed and kinda hates himself because his trauma turns him on.
Ken's first real sexual fantasy, which he relives over and over afterward, is Daisuke rescuing him from Oikawa in episode #45. Instead of freeing him and fighting Demon together, Daisuke slams him against the side of the truck or smashes his face into the ground and fucks him. The fantasy/dream varies in how rough Daisuke is and whether Oikawa touches him before Daisuke arrives.
Some of Daisuke's prominent fantasies include fucking in the locker room or on the soccer pitch after a mess. He enjoys the idea of almost getting caught thrilling and wants to push his luck.
Daisuke and Ken both have average-size penises. Ken's is slightly longer and narrower while Daisuke's has more girth. Daisuke is sensitive about being "small," which usually just makes Ken roll his eyes because there isn't that much of a difference between their lengths and he is well within the typical range.

bedroom dynamics

Daisuke is constantly aroused around Ken. Before he realizes his feelings, he thinks it's circumstantial and unrelated to Ken.
Daisuke finds it very sexy every time Ken says something really smart and when he kicks his ass when they play soccer or video games. He finds Ken unfairly pretty, especially with how graceful and agile he is.
Ken is turned on by Daisuke's often rash, headstrong attitude. Every time Daisuke says something particularly stupid, he's torn between amused exasperation and unapologetic arousal. He loves when Daisuke is a mess - dirty, sweaty, spilling his food/drink all over himself - and Ken desperately wants Daisuke to make a mess of him too.
They become addicted to pleasuring each other and cannot keep their hands to themselves. They're naturally inclined to understand each other via Jogress, but they are also dedicated to discovering and exploring each other's bodies.
They can achieve simultaneous orgasm because of Jogress.
Their heartbeats usually synchronize during sex.
Daisuke is a switch, both in regards to dominant-vs-submissive and top-vs-bottom, but Ken is a submissive bottom and rarely feels comfortable being assertive, so Daisuke is usually the one to lead their interactions.
Ken trusts Daisuke implicitly and wants him to use and control his body for his own pleasure. He wants Daisuke to physically claim him. This is a trauma response.
Daisuke is possessive and loves to cover Ken's body with hickeys and cum. Ken gives Daisuke hickeys too but not to the same extent.
Daisuke wants to do whatever Ken wants, but he draws the line at physical pain. He would never hurt Ken, even if Ken asks him to.
Ken has a deepthroating kink and wants Daisuke to hold him in place and fuck his throat. Daisuke is a little hesitant because he doesn't want to hurt him or treat him like and object, and it takes a lot of persuasion and winding him up for Daisuke to follow through. Daisuke is surprised and super turned on to learn that Ken can come purely from Daisuke fucking his throat.
Giving Daisuke a blowjob is one of Ken's favorite sexual activities. He's obsessed with drinking Daisuke's cum.
Daisuke is soft and gentle when they have sex, and he worships Ken's body to show him all the love and care and appreciate Ken deserves even when he thinks he doesn't.
Ken's body is very sensitive, including his nipples, and he can come untouched.
Daisuke is into the idea of having sex in weird and exciting places, but he's too possessive of Ken to actually want to do anything public or semi-public. Sometimes, they go to the Digital World to have sex somewhere more public. It's also very convenient as a place for them to meet up.
They enjoy having sex inside Imperialdramon.
V-mon and Wormmon are almost always present when they have sex. Digimon don't have genitalia or an understanding of romantic and/or sexual relationships so they don't fully understand what Daisuke and Ken are doing, but they know it makes them feel good and happy and support them. The Digimon often get playful, cuddly, and/or hungry when the boys get busy.
Daisuke and Ken are 100% monogamous and never use condoms.