I think Takamura wants to please the old man but knows that can't because of his blindness, that's why he needs Ippo to get back on track. As Ippo said, "that's heavy".
lol this forceful "marry me" thing in this manga just speaks loudly of the sentimental inexperience of the author. Its really cringy! I expected a bit more from this manga, which isn't bad but i would have liked it more if read at a younger age.