Long post, my headcanon for Ritsu's dating history.
After nth time rereading SIH, I'm still wondering how Ritsu had been in several relationships before he met Takano again, when he's so uninterested and avoidant in canon, with Takano/An/Nao... So here's my attempt at exploring Ritsu's past girlfriends and his approach to romantic relations.
-Ritsu didn't deliberately look for relationships, he stumbled into them
-He never stayed in a relationship long enough to figure out how to be considerate to his girlfriends (canon, he's so obtuse with everyone. Even Takano recognized An wanted to be invited to Ritsu's room back when she visited his apartment)
-He never treats his relationships casually, always tries his best to make them work before giving up (breaking up) when it seems hopeless
-Probably has 2-4 short relationships/near relationships, because An noticed it was a pattern.
-Ritsu might not realize this, but as he started feeling pressured by his parents' and society's expectations, he tend to gravitate towards self-assured people who seem to know what to do in their life (not always romantically; Ritsu was drawn to confidence and competency in people-->Takano & Haitani)
-Despite being so indecisive in the manga, Ritsu isn't the type to begin or stay in a relationship/situation he doesn't want to be in. He tends to make decisive decisions only when backed to a corner (resigning from his father's company, rejecting An/Haitani/Nao's confessions, asked Takano to not go to Yokozawa early in the story, confessed to Takano when he felt threatened by Kurusu). Takano was an exception, Ritsu was basically procrastinating from a combo of paralysis from overthinking & taking Takano's persistence for granted. So I think he has the capability to break up cleanly with his past girlfriends
-He never seem to be particularly hung up with any of his past relationship (aside from Saga), so I'm guessing he never really let himself be vulnerable with his past giflfriends, and nothing really extreme happened.
His first relationship after Saga was with his classmate in uni, who confessed to him. They were in a same semester-long group project, so they can be considered as friends.
Ms. A confessed to Ritsu, but Ritsu said he wasn't looking for a relationship at that time. After some more time, Ritsu agreed to give it a chance, because Ms. A was so genuinely nice, and he felt comfortable being with her... However, Ritsu wanted to break up after because she reminded him way too much of himself with Saga (she wasn't crushing on his looks; awkward; so sincere) + guilt knowing he couldn't return her feelings. They remain friends afterward; Ritsu still has her contact.
After that, he went for a long while just focusing on his studies, before Nao forced him to install a dating app (though Nao has a crush on Ritsu, I can imagine him doing this...). There he met Ms. K, who has this profile:
Ritsu contacted her out of curiosity, and this relationship developed in vague direction. Ms. K worked part-time as a barista, while she studied agriculture at uni. She was 1 year younger than Ritsu, lives with her mom and has a pet pug. She was the one Ritsu felt drawn to the most*, though he didn't really know why. Their relationship only lasted 6 months, before they drifted away due to conflicting schedules and different life trajectories. She was the one breaking up with him, they didn't remain in contact with each other after.
*she probably has vaguely similar traits to Saga: pensive, impulsive, self-sufficient, somewhat unguarded (can sleep with Ritsu around), blunt, has a soft spot for small animals.
Ritsu went on more dates (2-3) through the dating app, but mostly everything only ended with Ritsu and his dates having awkward dinner at sit down restaurants. After he realized he wanted to focus on work and didn't really want to have a relationship, he deleted the app. Some months later, he applied at Marukawa :)
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