From episode one I asked myself what I've gotten myself into. Since it's only seven episodes long, I didn't want to drop it, since the comedy was quite enjoyable, but that's the only thing this drama has going for itself.

The main character got went through basically zero character development and remained hopeless until the very end. The development of his relationship with his potential love interests... was it even there? Except for some forced kisses and his boss making moves on him, we don't see much, as in, Haruta didn't seem to be very interested in any of the two, he just seemed to go with the flow.
Haruta's character of the crazy and careless kind, he's often loud and can't take proper care of himself after his mother left the house. If you don't like characters like this, he will definitely annoy you to death (which surprisingly wasn't the case for me). What did bother me though, is, as I said before, he never seemed to show genuine romantic interest, even in the person he ended up with.

Maki as a character was okay, I don't have anything special to say about him except that he certainly deserved better.

Chief Kurosawa often had me cringing hard, but at least he knew what he wanted and had a clear end goal, in comparison to Haruta.

The best character, for me, was definitely Haruta's friend Teppei with his incognito songs and weird recipes.

In conclusion, Ossan's Love could have been really good.

It touched on a lot of ~incoventional~ love relationships, such as same sex couples or couples with a big age gap, which I really appreciate. But the execution was, in my opinion, very poorly done though,
I can't exactly pinpoint what, but something in this drama was missing. The plot and characters lacked substance, a little more backstory on some characters might've also been nice, but there's only so much you can do in a certain period of time. The way the story progressed was kind of chaotic and all over the place, even the editing could be described the same way in some scenes. Also, the way some characters would aggressively pin the other on the wall or grab them by the hand, it looked like it might've been actually painful.
This drama was definitely not what I expected, but it still left much to wish for.