It’s still unclear — the choice between grandma or yeowoon was prompted because the likability was too high at that point. The MC drastically dropping(?) yeowoon’s favorability balanced out the system to normal. Thus the choice between grandma and yeowoon became unnecessary
At least that’s my theory?
He had a timeframe to choose between them (you can see the countdown in the system panels in the beginning of ch 52), but he didn't.
That's why he was punished with the time reduction to complete the mission from 100 to 36 days.
Then, he received another submission of either keeping the only 36 days remaining or going back to 100 but with 0 favorability points. He chose the latter and that's why he broke up with Yeowoon on ch 53

wait what happened with that choice between mcs grandma and yeowoon? i thought he had to choose between the two but it started toward a different direction?