Most popular dating Sims usually have you pick a route. I've played many otome as a kid thosr are usually w/m. (Only recently has there been where you could be lgbt+ in games like so. ) Mystic Messenger was a w/m game with the option to "be friends" with the woman of the group. All characters had a bad bad ending, bad ending, friend ending and a good ending. It's usually when you help them solve their life problems and let them be emotionally vulnerable that leads to romance while being just a friend you solve their life problems w/out romance. The game he is playing seems Vanilla so the bad endings are just getting rejected. Others games might have more outta pocket endings like accidently joining a cult or something. Some of them are Dating sim with a massive side of story like The Arcana, some might be action/story games with a big side of dating Sims like Baldurs Gate 3. Overall, it's basically the same as any RPG game where there are many endings and it all depends of your choices.
Based on our boy I have a feeling he is failing bc he has the personally type where he is naturally helpful and easy to get close with but also dense and has hard boundaries when it comes to emotional vulnerability which is why while he can get them to all be friends he doesn't get past the romance, this is where his easy to get close with but harsh boundaries with emotional vulnerability clash. And when he does get past it he thinks that's just how you treat everyone and doesn't separate his actions for his goal partner. So the goal partner realized they aren't special and 'feels' lead on. That's where his helpfulness and denseness clash. Why he was able to get the friends ending, get the lead on ending n so on.
Sorry this is so long but hope it was helpful
No problem and I get you. If you're interested then I think you might like the Visual Novel game genre instead bc those can be a thing without romance.
If you'd like some recs here's 2
Slay the Princess (many possibilities and ending, cosmic, 4th wall break, existential crisis)
Our life: begining and always (cozy game, your growing up, romance is an option but easy to turn off/avoid it all depends on your input, personally I loved the family dynamic You get two moms and they make you feel soo loved)
Sorry if this was a ramble, most my friends don't do these types of games so I'm always a bit excited to talk about them.
idk any dating sim-esque games other than 'episode'(s?) (i'm more of a fan of open world games) so i have no idea what i'm supposed to expect or how difficult this is supposed to be
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