Writing on Future Headcanons of my ocs:
Disclaimer: I only took ships I could write a Lot about and have some development already or some ideas, Not all Leroy ships are here
Leroy x Catherine @thetwstwildcard
-The Future of them will Mainly depend on which of these scenarios Happen:
1. Catherine dies through the saving of the Jabberwocky,
Leroy is devestated and tries to live the Rest of His Life to Honor her and follow her dream and make Songs dedicated to her. It will be hard for him to Fall in Love again so maybe He would Take around more than 10 years to accept someone else in His Life.
2. Leroy dies protecting her
Catherine might have won freedom but at the cost of someone dear to her and given Leroy posed as her to protect her. She probably also will Take a while to get used to Life without him.
3. Happy Ending they all find a way to save Catherine and she can be free,
Leroy and Catherine start Dating and become a couple with time. Leroy for Catherine became a bit nicer to Riddle, He still dislikes him but He won't prank him anymore. They still tease each Other but in a loving way. And also they totally would have the usual bickering but much less than before they we're a couple. They graduates and then moved together.He probably proposed as Catherine started of with her Band on Stage, which Made her Hella emberassed. However with time Leroy became the more shy and emberassed while Catherine could corner him now compared to before. Leroys Mom would be fine and in this Relationship Leroy would ignore His Yakuza father given Catherine is more important. They did their best to get away from her Family after all. And Overall they be a couple who Talk about old Times are paid Back and Just want to have fun.
They got a Daughter named Heather which was quite a troublemaker.
I really feel like given they had a hard time before Overblot with distrust from Leroy but after Overblot the would warm Up to Suffy. Maybe even try to close the Chapter with both telling Susan they won't listen to her and find their own way. It Starts as Work colleagues, Leroy helping Suffy with Some of His emotional scars and so letting accidently Out that He Likes them a Lot for who they are. With this they kinda started to try Dating, also with slight troubles at First but with time they noticed they Like each Other a bunch. Leroy would surprise them with Gifts and get flustered by sudden affection from Suffy. After Graduation He introduced Suffy to His mother. His mother got worse with her Condition and Leroy was Sharing some Details about His father but I feel like there is some Angst as Leroy once vanished a night and came Back with wounds and bruises. Suffy was worried sick and Leroy told it would be fine, He settled it. Some years later they both Had a Job, Suffy in daycare, Leroy as Restaurant owner and Leroy proposed to Suffy with a Bouquet Gift.
They adopted a orphaned Child who ran to the daycare and became quite a lovely couple with time.
Leroy x Alyn @in-that-deep-blue-sea
This one mainly started as lowkey Work flirting Where usually Leroy would be the one to fluster her but she could comeback sometimes. She developed a crush whilehe was still occupied with His Student Life. One day she dropped her bag and Leroy helped her gather everything, which is how He found a Game in her bag and as she was emberassing He actually smiled and suggested they could play it together later. So their secret meetings to game together started. It made them grow really close. Then the day came His moms Condition got worse and He wanted to Sneak Out to confront His father which Alyn noticed. He came Back with a wound in His arm and ehr crying for him. He promised to never worry her again and that He is sorry He didn't Tell her sooner. She treated him and told him a Story about her past, He then also shared more about His. They kept His wound a Secret for some days.
I feel like Alyn confessed to him one day by dragging him to the courtyard at Night. From then on she helped him become His old self a Bit more and He found a mixture of His own Style.
They graduated, they both Went Into the Same company, she as Manager He as worker. They at first tried to Provider for medicines for Leroys mother and He also introduced Alyn to all His Family. And probably proposed secretly in Work through a Note one her Table. To meet her to a Dinner at Night.
I can't remember If we Made some but I can either See them have a very pretty Daughter or a fun son.
Leroy x Eira @just-patchy
I feel like Leroy hid from Riddle in the gardens. I also think she would make Leroy less of a annoyance to Others given He would Care more for her and try to find Out at First why she is wants distance from her. As He finds out about her Condition He actually was drawn in more given He didn't want her to be alone. He knows how it feels to be alone so He would want her to feel Like Someone Cares for her. Slowly she would listen to His troubles and Accept that He is trying to be carefull around her. He would try to find some ways to maybe make it easier for her to be around people.
Leroy mother would also get better thanks to Leroy experimenting in the kitchen with Alchemy and Medicine I believe.
Leroy in this Future could become a pharmacist and cure many people. The Yakuza father of him is fully ignored. I can also see a very flower themed wedding between them. Aside that I can see them also find a way to have a kid and be happy.
The most chaotic couple to emerge. From Leroy being annoyed from her breaking stuff at his work, to him helping her out many times and them finding odd things in common to a teasing but comforting way. After overblot I feel their relationship go much better, given before he could have been a asshole sometimes. Starting like awakward bro friends who do stuff to Leroy telling a bit about his broken family and them laughing about the situation and slightly Leroy accepting to be more himself even though he can be looked at weird. They do still bicker sometimes but sometimes they are also dumbasses on the same wavelength. She also played a lot in with his pranks later because some of them just seemed to hilarious. I feel Leroy before he could ask to marry Yoru had to beg Crowley more than 10 times till it worked. And he tooks as long to get her to understand it... Aside that I think he would stay a mechanic in the future with Yoru. They have a more birdlike kid which is very fond of scaring others. Whereever it takes them, they are there to cause chaos, despite Leroy sometimes having a bit more reason in certain actions. He accepted his life as house husband though. Leroys mother died early in this, but Yorus words mainly snapped Leroy out of his idea to confront his father.
Leroy x Ellen @multydoodles
Well the endless bickering married couple. It went from both just basicly getting into fights over a misunderstanding to Leroy actually secretly enjoy this and teasing her, to him developing a slight crush as well as her but both are too dumb to notice that they crushing. I do feel close enough they would share their troubls if the other notices about their family as we wrote already and after that they bicker a bit less and have a more friendly attitude. Love thought.... nah it can’t be... or can it. Leroy asked that in his 3rd year as he joked to Ellen about that idea probably and she was like: “God finally you noticed.” I can at least see something like that. Marriage at a scary mansion I can see and them overally still being fond of scaring others. Leroys occupation... might also this time make a bakery with halloween theme things and especially candy. Had a kid which became a little shit and causes chaos for them while they relax proudly in their home and still take care of Leroys mom who is still pretty sick. Amanda was very happy Leroy found someone like Ellen and enjoyed her company.
If you still have a Leroy ship and want one of those writings I can try, but these are the ones I had in my mind to determine some of Leroys futures. I can also do for some of the others where I think he would confront his father or where his mom died here:
Leroy x Amelie: Probably lived at least a lil long and his dad he ignored
Leroy X Vinh: Mom died earlier, wanted confront his Father, Vinh stopped him
Leroy x Rozaline: Mom was semi- long alive, Fathers clan only threatened them once and left
Leroy x Kalli, Similar to Roza, maybe more influence of the Yakuza
Leroy x Aster, No Yakuza, Mom was sick but still alive for a while
Leroy x Evangeline, some Yakuza angst and Them protecting his mom but resolved ok
Leroy x Charlotte, no Yakuza influence, a lightly sick mom
Leroy x Beth, Mom died early, Leroy protected more Beth and was worried
Leroy x Alina, No Yakuza, she met Leroys mom, but then died a year later,
Leroy x Mimi, A pretty happy one, Mom lived ok long and Yakuza didn*t get involved
Leroy x Rae, Similar to Kalli I think.
Anyways if I do a Henry one it will be more about if he still has contact to his family or nah. Don*t know how many I do off these.