Kim Eun Sook is a huge name in the kdrama industry. We could argue how well deserved that is or not. While I do think Goblin is still the best kdrama ever produced, I'm not sure if the script & more specifically the plot is why. With that said Gentleman's Dignity to me is by far the worst of her works I've seen so far. There are so many problems with the script that it's difficult to list them all & frankly this drama isn't really worth watching in 2023. (which I just did for the first time) You could argue that it's just dated & I'm looking at this with the wrong mindset, but then why do I find Secret Garden being so much better in every way imaginable despite being 2 years older?

Even if I ignore the miscellaneous problems with the plot, the base setting itself is already bleeding from multiple wounds. Out of the 4 male leads two of them are just the baddies, one of them -started out as- a womanizer & another just threw away her lover like a trash bag, because he has fallen in love with someone else. To me If I cannot empathize with the most important characters, then it will be difficult to enjoy any drama. (the other 3 try to help cover up the cheating as well, but then suddenly he is not really a cheater, because the writer decided to completely rewrite his personality to fit the plot direction)
There is also a lot of backward crap about Korean society that I always hated in kdramas.

I could even say this is basically the gutted version of a typical -bad- family drama. By gutted I mean most of the fluff is removed & there are no plotlines involving the elderly. However the whole shebang with a long lost first love & a mysterious high school kid returning home to Korea plot seems very typical.
Also what is Kim Woo Bin doing in this drama? Did they just cast him as eye candy & created a very random inconsequential role for him?

There are some reasonably funny moments, but overall the comedy is not very convincing.

(Much like Secret Garden this drama too has some really cool iconic outfits..)

So yes, I cannot recommend watching this, there are far better retro titles out there. Even the ancient My Girl from 2005 is a far more enjoyable drama than this.