(Sooper long feedback alert!)
This was REALLY interesting. My jam game was a conversation sim too, so of course this was right up my alley!
When I first got into the game, I spent a long time staring at the controls, yet when I pressed Start, I was totally overwhelmed and confused. This might be what you were going for, but introducing the mechanics more gradually, say with an interactive tutorial, would help a lot. It is also very visually busy and fragmented, so try finding ways to make the elements simpler, easier to focus on, and make more sense together. (For example, the teddy bear is really cute and makes sense as a "lolrandom" thing, but it could be contextualized a bit more. You could have the player's character daydream about it before the gameplay starts.)
Once I got the hang of the system, though, I was able to appreciate how clever some of the ideas were. I love that the answers scramble themselves if you mess up on the minigame, and that there's often more than one good answer to the questions. The sheer amount of questions and answers is awesome as well. However, it was often very frustrating when the guy seemed to respond to a different option than the one I intended. I might have taken my eyes off the clock (which is awfully tiny considering its importance), tipped the scroll wheel a bit, or bumped into something right before time ran out.
The dialogue is well-written too, but sometimes unnatural or unfitting. He asked me a lot of "icebreaker" or even job interview-style questions to the point where I started to wonder where he was reading them off of. 🤣 Sometimes he'd overreact or underreact to awkward choices, too. One time I selected a horrific option like "we're celebrating a miscarriage", and he acted freaked-out for a moment before immediately asking another question (even calling me "friend") as if nothing happened. Try adding more specific categories for answers and creating more transitional dialogue.
The text to speech was also very helpful. It's somewhat realistic, but not quite. (You could find ways to roll with it though. For example, you could anthropomorphize the other person into a robot who simply acts like a human.)
Anyway, this is a really cool concept and I enjoyed playing it. Keep up the good work!