✦ Obey Me! Brothers as Boyfriends ✦
I've seen a lot of boyfriend headcanons that either turn the brothers into perfect green flags or make them wildly OOC, so I wanted to try something a little different.
These headcanons are based as closely as possible on their canon personalities, official lore, character flaws, and relationship dynamics throughout the game.
This means you'll find both the good and the bad.
Because loving someone isn't just about their best qualities.
It's also about the habits, insecurities, baggage, and flaws they bring into a relationship.
Some brothers may come across more difficult than others, and that's intentional. The goal isn't to make them ideal partners—it's to explore what dating them might realistically look like while staying true to who they are.
⚠️ Warnings: • Canon-typical flaws and unhealthy behaviors • Jealousy • Emotional dependency • Possessiveness • Poor communication • Insecurity • Workaholic tendencies • Anger issues • Manipulation (where applicable) • Discussion of trauma and emotional baggage • Not intended as relationship advice • Slightly critical analysis of characters while still appreciating them
As always, these are just my interpretations based on canon material.
Feel free to agree, disagree, scream in the tags, or defend your favorite demon.
Now let's talk about the seven Brothers I affectionately call husbands.
This is for you, sweetie:
✼ •• ┈┈┈┈๑⋅⋯ ୨˚୧ ⋯⋅๑┈┈┈┈ •• ✼
The Vibe: The responsible, dignified boyfriend who acts like he has everything under control… but secretly melts just for you.
- Your Personal Protector & Provider: Lucifer takes his role as your partner very seriously. He will move mountains to keep you safe, comfortable, and happy. If you mention even in passing that you like something, it will appear on your desk the next day—no questions asked. He has a soft spot for spoiling you, even if he acts like it’s “just a trivial matter.”
- Quiet, Intimate Affection: He’s not big on PDA, but in private, he’s incredibly gentle. He loves resting his chin on top of your head while you sit together, or holding your hand so firmly but softly that it feels like he’s afraid you’ll disappear. He remembers every little detail—your favorite tea, how you take your meals, even the exact time you usually go to bed.
- Your Biggest Supporter: When you’re stressed or working hard, he’s right there. He’ll sit with you while you study or work, going through his own paperwork in comfortable silence, and will gently correct you if you make a mistake—but always with the intention of helping you grow. He’s proud of you, even if he rarely says it out loud; you can see it in the way his eyes soften when you walk into a room.
- Romantic in His Own Way: He plans sophisticated but meaningful dates—late-night walks in the Demon Lord’s Castle gardens, private concerts, or quiet evenings by the fireplace. He loves dancing with you, even if he acts like it’s just to “practice proper etiquette.”
- Overbearing & Strict: His sense of responsibility and need for order can sometimes feel suffocating. He might try to schedule your time or tell you what to do because he thinks he knows what’s best for you. It comes from care, but it can feel like he’s treating you like a child rather than an equal.
- Poor at Expressing Feelings: He struggles to say “I love you” openly or talk about his own worries. He often hides his stress and exhaustion behind a calm facade, and he hates showing weakness. If you push him too hard, he might get defensive or pull away to work alone instead of talking it out.
- Workaholic Tendencies: He gets buried under piles of paperwork and meetings, and there are days where he barely has time to breathe, let alone spend time with you. He feels guilty about it, but his duty as the oldest and Diavolo’s right-hand man always feels like it comes first.
The Vibe: The self-proclaimed “Great Mammon” who acts like he’s too cool for feelings, but is actually completely wrapped around your finger.
- Unwavering Loyalty: Despite his greed and troublemaking, Mammon is the most loyal boyfriend you could ask for. Once he’s fallen for you, he’s yours forever. He’d sell every single Grimm he owns and face any danger without a second thought if it means keeping you safe. He calls himself your “first demon” and takes that title very seriously.
- Clingy & Affectionate (Secretly): He acts like he’s only spending time with you because he “has no choice” or because you owe him something, but the truth is, he hates being away from you. He’ll find excuses to be near you—offering to walk you places, “accidentally” showing up where you are, or wrapping his arm around your shoulder like it’s the most natural thing in the world. He loves physical affection: holding hands, hugging, and having you sit next to him.
- Thoughtful in Unexpected Ways: He might spend money on gambling or flashy things, but when it comes to you, he’s surprisingly thoughtful. He’ll see something that reminds him of you and buy it—even if it’s something silly or cheap—and then pretend it was “just lying around” or “you’re lucky I felt like getting it.” He remembers things you like too, even if he claims he forgot.
- Fun & Energetic: He’s always up for an adventure! He’ll take you out to fun spots in the Devildom, try new foods with you, or play games until late at night. Being with him means there’s never a dull moment, and he’s always there to cheer you up when you’re feeling down—even if his methods are a little chaotic.
- Tsundere Denial: He struggles to be honest about his feelings. He’ll call you an idiot or a dummy one minute, then panic if you seem upset. He’s terrified of being vulnerable, so he hides his affection behind teasing and excuses. It can be confusing at first to tell if he really cares.
- Trouble & Impulsiveness: He gets into debt and messes up constantly, which can be stressful. He might make promises he can’t keep or drag you into his schemes without thinking. He doesn’t mean to hurt you, but his poor choices often lead to problems you both have to deal with.
- Jealousy: He gets jealous very easily. If you pay too much attention to his brothers or anyone else, he’ll get pouty and moody, even if he won’t admit it. He’s insecure deep down—afraid that someone “better” will come along and take you away from him.
The Vibe: The socially anxious introvert who sees you as his “Player 2” and the only person who truly understands him.
- Deeply Devoted & Accepting: Levi has always felt like an outcast, so when you choose him, he cherishes you more than anything. He accepts you exactly as you are—flaws and all—and expects the same in return. He treats your relationship like a precious, rare treasure, and he would never intentionally hurt your feelings.
- Your Personal World: He loves sharing his passions with you. Whether it’s showing you his favorite anime, manga, games, or explaining the lore of TSL, he lights up when you listen. He loves doing “co-op” activities—playing games together, watching marathons, or even building model kits side by side. To him, just being in the same room as you is enough.
- Gentle & Attentive: He’s incredibly observant, even if he doesn’t look like it. He notices when you’re sad or tired, and he’ll quietly bring you snacks, lend you his favorite blanket, or let you use his gaming chair. He writes down little things you say so he can get you the perfect gift or plan the perfect date.
- Romantic in His Own Way: He expresses love through references and small gestures. He’ll compare you to his favorite fictional heroines, write you cute notes, or create custom playlists just for you. When he finally gains the courage to say “I love you,” it’s the most sincere and heartfelt thing you’ll ever hear.
- Extreme Self-Doubt & Anxiety: He constantly thinks he’s not good enough for you. He’ll say things like “Why would someone like you be with a gross otaku like me?” This insecurity can sometimes make him withdraw or overthink every little thing you do. He might even try to push you away because he’s scared you’ll eventually leave him.
- Social Avoidance: He hates going out in public or being around large groups of people, especially his brothers. Most of your dates will be in his room, which can feel limiting if you’re someone who likes going out. He gets overwhelmed easily and might shut down if there’s too much noise or attention.
- Obsessive Tendencies: He can get so absorbed in his games or hobbies that he loses track of time and forgets to spend time with you. He might also accidentally compare real life too much to fiction, which can lead to misunderstandings if you don’t share his enthusiasm for certain things.
The Vibe: The refined, book-loving scholar who hates being compared to Lucifer, but loves sharing his world with you.
- Great Conversationalist & Teacher: Satan is incredibly smart and curious. He loves talking about anything and everything—literature, history, magic, philosophy, even silly debates. He’s patient and loves explaining things to you, and he admires your thoughts and opinions. Being with him means you’ll always be learning something new.
- A True Gentleman: He is polite, respectful, and thoughtful. He opens doors for you, listens when you speak, and treats you as his equal. He loves bringing you to bookstores, libraries, cat cafes, or quiet parks. He’ll read aloud to you, or let you rest your head on his shoulder while he reads.
- Soft & Compassionate: Underneath his cool exterior, he has a huge heart—especially for animals. He adores cats, and he loves that you care about them too. He’s very empathetic; if you’re having a bad day, he’ll sit with you, listen, and help you sort through your feelings calmly. He writes poetry and little notes for you when he’s feeling particularly affectionate.
- Reliable & Honest: He values truth and fairness. He will always be honest with you, even when it’s difficult, and he’s someone you can trust completely. He’ll stand up for you and defend you without hesitation.
- The Wrath Within: His greatest struggle is his anger. When he gets upset—especially when Lucifer is involved—he can lose control. He tries very hard not to take it out on you, but sometimes the frustration bubbles over, and he might say harsh things he doesn’t mean or isolate himself. He feels terrible afterward, but it takes time and patience to help him manage it.
- Coldness When Upset: When he’s hurt or angry, he tends to shut down and become distant and sarcastic. Instead of talking things through, he might hide in his room or read to avoid dealing with emotions. He finds it hard to express vulnerability, fearing it makes him weak or too similar to Lucifer.
- Obsession with Revenge: He can get caught up in his schemes to prank or annoy Lucifer, sometimes forgetting that it might cause stress or trouble for everyone else. He struggles to let go of grudges, which can affect the mood in the house.
The Vibe: The charming, beautiful socialite who acts like he only cares about looks, but is secretly searching for true, unconditional love.
- Overflowing Affection & Compliments: Asmo is the most openly affectionate boyfriend. He showers you with kisses, hugs, compliments, and pet names constantly. He thinks you are the most beautiful person in existence—inside and out—and tells you every single day. He loves making you feel desired, loved, and confident.
- Your Personal Stylist & Cheerleader: He loves dressing you up, doing your hair, or picking out matching outfits. He takes pride in showing you off, but more importantly, he genuinely wants you to feel good about yourself. If you’re feeling down about your appearance or abilities, he’s the first to hype you up and remind you how amazing you are.
- Fun & Understanding: He’s very emotionally intelligent and easy to talk to. He doesn’t judge you; he accepts every part of you. He loves taking you to parties, fashion shows, or shopping sprees, but he also loves quiet nights in doing face masks, painting nails, or just gossiping and laughing together. He’s always there to listen when you need to vent.
- Romantic & Devoted: Even though he’s popular and gets attention from everyone, he is completely faithful once he’s in love. He wants to know every single thing about you—your dreams, your fears, your favorite things—and he loves planning dreamy, glamorous dates just to see you smile.
- Superficial Defense Mechanism: He hides his deep feelings behind a mask of vanity and flirtation. He acts like he’s only interested in beauty and pleasure, but this makes it hard for him to open up about his true fears—especially his fear of being loved only for his looks and not for who he is inside.
- Jealousy & Insecurity: Despite his confidence, he is deeply insecure. He worries that you’ll leave him for someone “more interesting” or that you’ll get tired of him. He can get overly jealous if you spend time with others, and he might flirt with others just to test your feelings or make himself feel better, even if he doesn’t mean it.
- Self-Obsession: He can be very focused on himself and his appearance, sometimes unintentionally making things about him. He might forget to ask how you are or get upset if you don’t react the way he expects to his stories or compliments.
The Vibe: The sweet, strong athlete who lives to eat and protect the people he loves.
- The Ultimate Gentle Giant: Beel is physically intimidating, but he is one of the softest, kindest souls you’ll ever meet. He treats you with such care, like you’re something precious that could break. He’s incredibly warm and comforting—his hugs are the best in the Devildom, big and safe and warm.
- Unconditional Love & Generosity: He loves sharing everything with you—especially food! He’ll always save you the last bite, buy you snacks whenever he sees something you like, or even cook for you if he knows how. He doesn’t care about status or looks; he loves you simply for being you. He’s always honest and straightforward—no games, no secrets.
- Your Shield: His protective instinct is unmatched. If anyone even looks at you the wrong way, Beel is there, standing tall and ready to defend you, though he’ll never hurt anyone unless absolutely necessary. He walks on the side of the road closer to danger, holds your hand tightly in crowds, and checks on you constantly.
- Simple, Comforting Happiness: Being with Beel is easy and peaceful. He enjoys simple things—sharing meals, watching sports, exercising together, or just lying down and talking. He’s a great listener; he might not always have the perfect words, but he will always listen and be there to support you no matter what.
- Constant Hunger: His insatiable hunger is a part of him. Sometimes, it feels like food comes before everything else—even you. He might forget plans because he stopped to eat, or accidentally eat something important (like your homework or a gift) without realizing it. It’s not that he doesn’t care; it’s just a primal urge he struggles to control.
- Difficulty Expressing Emotions: He’s not very good with words. He feels things deeply, but he struggles to put them into sentences. When he’s upset or confused, he might just eat more or stay quiet instead of telling you what’s wrong. He also carries a lot of guilt and sadness about the past (especially regarding Lilith and Belphie) that he rarely talks about.
- Physical Strength: He doesn’t know his own strength sometimes. He might squeeze your hand too hard or accidentally break something while trying to be helpful. He also feels immense guilt if he ever loses control of his hunger and causes trouble.
The Vibe: The sleepy, sarcastic youngest who acts like he can’t be bothered, but will move heaven and earth for you.
- Extremely Comfortable & Relaxing: Belphie is the master of “chill.” He doesn’t demand much, and he loves nothing more than having you curl up next to him while he naps. Being with him feels like coming home—no pressure, no fancy expectations, just peace. He loves sharing his dreams with you and listening to yours.
- Playful & Teasing Affection: He loves teasing you—calling you cute nicknames, poking fun at your habits, or pretending to be annoyed when you wake him up. But it’s all done with love. When he’s in a good mood, he’s very affectionate: he’ll wrap his tail around you, rest his head on your lap, or hold you close while he drifts off. He says the sweetest things when he’s half-asleep and his guard is down.
- Deeply Loyal & Protective: Despite his laziness, if you are in danger or need help, Belphie will wake up instantly and move faster than anyone. He has a fierce protective streak, born from losing his sister once and being afraid of losing anyone else he loves. He trusts you completely and lets you see parts of him no one else does.
- Great Listener: When he’s awake enough to pay attention, he’s actually very insightful. He’s observant and understands people better than he lets on. He’ll listen to you ramble for hours without interrupting, and he’ll give you honest, no-nonsense advice when you need it.
- Extreme Laziness & Negativity: He sleeps most of the day and hates doing anything that requires effort. He might cancel plans because he’s too tired, or refuse to go anywhere unless you drag him. He also has a tendency to be pessimistic and cynical; he can be very blunt and say things that sound harsh, even if he doesn’t mean to hurt you.
- Emotional Walls & Past Trauma: He has a lot of unresolved pain and anger from his past. He can be moody, distant, or sarcastic when he’s thinking about things he doesn’t want to talk about. He struggles to believe that happiness can last, so sometimes he acts detached or pushes you away just to see if you’ll stay.
- Manipulative Tendencies: He’s clever and knows how to get what he wants—usually by pretending to be sleepier or weaker than he is. He might try to convince you to skip responsibilities or do things for him. While he would never hurt you now, he can be very stubborn and hard to reason with when he’s set in his ways.
