(Thank you Quenlyloony for requesting! If this isn't what you were exactly looking for, or if you want some changes, let me know! Sorry for the wait as well.

♡S/O headcanons♡)

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☆~ Keith (Bf)

-He has done small singing shows for the school, such as campaigns and donations, in which the school wants to thank him. They decide to reward him with a large painting, but they don't know who is a good painter.

-That's where you stepped in and offered to paint it. The school provided you with the resources needed and it seemed to make sense, considering you are his boyfriend.

- He is generally easy to paint and this wouldn't be the first time painting him. Through, you painted a chibi version of him, so painting a larger, more accurate version of him was going to be a new challenge that you are willing to take.

-He has spiky blue hair and simple thrift store clothes, so his character design isn't too complex, which makes the process of painting easy for you.

-When the school shows him the painting and informs him that you are the official artist, he is left in tremendous tears that may last for hours. He tends to be dramatic with some of his reactions but you don't mind, in fact, you find them pleasant.

-His arms flail around in excitement and he gives you massive hugs, sometimes you cannot escape the inevitable hugs when you give him gifts.

-He will definitely give you a bundle of kisses, his favorite spot is your cheek. He finds it exceptionally cute if he finds paint on you still. He will try to wipe it off and presumably fail.

Painting result:

(Art by Alizetha1 on Twitter)

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☆~ Gabby (Gf)

-One thing she loves is classical and modern art, especially when they are combined into a masterpiece. Unfortunately, you aren't Picasso but you had an idea on how to express your love for her in a form of painting.

-Since she is quite popular and her parents are pretty known around town, you told her parents your plan. With this in mind, the parents showed you a location downtown to paint. Legally, of course.

-Thankfully, Gabby's parents gave you all the supplies that you needed. You spent hours painting a mural with bold colors, mainly blue and red. You wanted to capture her in her battle outfit, which is her typical red dress.

-In the end, you had a lot of red, blue, and purple paint all over you and the outfits you wore when painting. It was hard keeping this a secret, considering it was in the downtown location where many people visit.

-The day you revealed it to her, she squealed. She took many selfies with you, the painting, and herself so she can post them on her social media. She couldn't thank you enough and she wanted to make it abundantly clear that she loves you. She took a lot of pictures of her kissing your cheek and posted them with your permission.

-In the end, she couldn't stop obsessing with the painting and she is thankful that it's in the town. This painting was the talk for an entire week straight at school.

Painting result:

(Art by ? - Found on Pinterest, posted by xioizzfunkin)

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☆~ Pico

-You wanted to try out a new spray paint so you decided to go to an underground railroad and spray paint in an abandoned location that many people paint at. It was free and the local authorities didn't care about the location.

-It reminds you of Into The Spiderverse movie, and because of that, you get scared whenever you see a spider. Regardless, you would spend hours at a time in that place to spray paint.

-You wrote some of Pico's lyrics of his songs around the painting of him, which you made in great detail since his design is also simple. It might get destroyed in the future by other teenagers, but for now, you are thankful for this spot. It was one of the first places you hung out with Pico, ironically.

-The day you showed him, he questioned why you two were heading under the abandoned location. You tried to play it casually. But when you got to the entrance, you had to turn on the lights and cover his eyes.

-"What is going on?" He asks, almost in an unamused voice. Of course, he loves any gift you give him, it's just part of his edgy teenager self coming out.

-You reveal the vibrant painting of him in a very energetic way and he stands there for a moment. Eventually, he comes by and inspects the details.

-In the end, he almost tackles you and gives you a tight hug. He then declares that he will make a better spray paint masterpiece for you.

Painting result:

(Art made by thegreatrouge on DeviantArt)

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☆~ Skid and Pump

-Any gift to them is worthy whenever you give them it. They always fight for which gift is the better one so sometimes you have to give them a gift that they can share.

-For this one, they love it when you express yourself through painting. They love typically anything you do that involves art and expressing yourself, which is perfect for you.

-You found a location under a bridge to paint a large mural for fun. They love purple together so you decide to use purple in your mural as well. In dedicated hours, you devoted your time and energy to this piece to impress both of them.

-They had to ask where you went after school since they constantly wanted your attention. It was hard lying to them, mainly because you didn't want to hurt their feelings and you didn't want them spying on you if they detected you were lying.

-By the time they discovered it, it was already done. They snuck up on you one day as you were making finishing touches. They both stared at it in awe and kept asking you questions.

-"You made that?"
"How long did this take?"
"Is this where you have been going?"
"Why is it so good?"

-They wrapped you in a bundle of hugs and were happy to see their new gift. They said they will visit it at least once a week to make sure no one ruins it. Gosh, you love this high schooler dorks.

Painting result:

(Art made by rougethebruh on Twitter)

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☆~ Witty

-He mentions before that if you were to hand him a gift, he didn't want it to be public. Public display affection usually embarrasses him and he prefers if you two were alone.

-Finding a location to paint a picture of him was tricky. Luckily, in a creepy alleyway where many rappers go to battle, you found one of his favorite spots. People don't usually go to this location since he claims it for his own, as rappers apparently claim their own spots when they battle.

-You had to ask for permission first (you didn't spoil the surprise but rather told him that you wanted to paint there) and he didn't mind much. The only downside was that he couldn't go to the spot for a few days, but you assured him that the gift will be worth it.

-You wanted people to know that this was his main territory. Everyone knows he isn't an artist-type guy, so having a painting of him by an anonymous person (that person being you) will let people know that he has a word around town.

-In his passion for rap battling, he has so much dynamic and that is what you wanted to recreate in this piece. The alleyway is dingy and still, so creating an atmosphere with a motion-like picture was the perfect touch.

-You weren't going to lie, you were a little nervous to show him. Nonetheless, when you told him it was complete, you wanted to see his reaction.

-He stared at it for a while and poked the painting to check if it was real. Witty was surely shocked at the masterpiece and said a lot of quiet compliments in hopes that you wouldn't hear.

Painting result:

(Art made by MagnaG)

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☆~ Daddy Dearest and Mommy Mearest

-You explained to them that you needed to do a project for school (which is a complete lie) and asked if they can help you pick a location and buy your materials.

-They both agreed, but choosing a location was exceptionally hard, so you had to settle with a large canvas. It wasn't much but you were alright with it.

-You painted to make sure you got the details of them both. Painting the two of them was harder for you so the detail work took more hours than you hoped. You wanted to do this so you can show how much you appreciate them without having to spend much.

-Once you went over the finishing touches a dozen times and waited a few days to make sure it was dry and protected with some gloss, you showed them the result.

-Mommy Mearest gave you the most bone-crushing hug you have ever experienced and Daddy Dearest pointed out all the details. You had to tell them that it wasn't actually for a school project. With that, they decided to hang this painting on the walls of their house.

Painting result:

(Art made by BenzBT on Twitter)

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☆~ Takeda (Senpai)

-You were excited to paint him. Takeda ended up being the cutest boy in the high school yearbook and he wanted to challenge girls to paint him for the fun of it. Many of his fangirls participated and you originally told him that you weren't going to.

-You ended up giving in and made an anonymous entry into the art competition. You didn't want to be excluded, especially since you are his significant other.

-You spent a long time painting in the art room after school hours and Takeda always questioned why you were there. You told him that the art teacher wanted you to help him with the freshman paintings and help the art teacher put them on display in the hallways.

-You were happy with the result when you finished and you had to make sure to get a lot of paint off of your clothes to get rid of the evidence.

-Somehow, in the depths of all the participants and other paintings, you managed to get the highest vote. One of the requirements was not voting for yourself so all the girls wouldn't do so. You even heard girls in the hallway become jealous at the entry that no one knew of (the only person who knew you got first prize was the art teacher)

-You got the first prize gift, which was a blue ribbon and showed Takeda at the end of the day. He literally snatched the first place prize ribbon from your hand and glanced back and forth between the ribbon and you.

-Outside in the schoolyard, he kisses you numerous times and begins to say how proud he is. He wouldn't stop saying how amazing you are and during that week, he ended up bragging about you to the other girls.

-You forgot the paint on your face during the day you showed him the ribbon. "You still got paint on you... Let's go my shower and clean that off~" And that's when you push him off, scoffing playfully. What a flirt.

Painting result:

(Art made by PinkCocoo2311 on Twitter)

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☆~ Lemon Demon

-In the confines of your bedroom, you wanted to paint a picture of the demon who lives in your closet. You always have creepy nightmares about him and scenarios would run your mind.

-Paint him with blood? Scary atmosphere? Maybe paint him dominating the world? You weren't sure what was running through your mind but you still wanted to create a painting.

-A creepy painting would suit him well. You didn't want to make anything cutesy since the demon doesn't usually like cute things when applied to him. He will cuddle you like a plushie and call you adorable all he wants, but the moment you call him cute, he gets upset like a toddler.

-This painting wasn't a surprise for him since he watched over your shoulder when you painted. At first, he didn't know what you were painting, but the result was very well and much better than you expected.

-Your parent/s didn't question why you made a painting, they thought it was a character you made in your head. Lemon Demon absolutely loves the picture and refuses to let your parents touch it (by hiding the painting in various places)

-He wouldn't stop holding your hands and kissing them. Numerous times he said you have amazing artistic abilities and he loves it.

Painting result:

(Art made by toffie_stars on Twitter)