 If you liked
Saikyou Densetsu Kurosawa
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 ...then you might like
Tokyo Tarareba Musume
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Older-than-typical protagonists oscillate between regretting the past decisions they did (and didn't) make, and moving forward. Contrary to the other recommendation, I don't feel that these manga are TOO similar - Kurosawa is portrayed as a lifelong loser who never found his niche, while the Tarareba Girls are (for lack of a better word) normies who just think they've aged out of the prime dating market - but they work very well as a spot-the-differences exercise in how josei and seinen manga treat thirtysomething angst in women and men.
Someone must be thinking why did I recommend a josei with a seinen manga?
Well both of them have "old" MCs, Kurosawa is 40 and something years old and the girls of tokyo tarareba are 33.
Both of the stories talk about older people that regret their past, that feel the time passed too fast, and that suddenly had a kind of a snap and decided to change (before it is too late)
Besides, both stories have the same feel about them. They are dramatic comedies - you laugh a lot and then cry in the same chapter. They are really depressing, but enganging, and both had me
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