Both female leads are dumped by their finances the day before the wedding and get a 2nd chance at love. Both shows are done by tvN so they have a similar vibe as well!
Pinocchio and Uncontrollably Fond give off a similar vibe. The shows focus on characters who's lives are intertwined in both the past and present and both shows deal with parental issues that may or may not affect the relationships between the main characters.
Both 38 Task Force and The Con Artists focus on conning and quests to acquire money. 38 Task Force deals with conning owed tax money while The Con Artists is about a big heist for personal benefit.
Both shows focus on a female lead that discovers she has a terminal illness and follow her story as she falls in love.
Both shows feature boybands (one already famous and one that has yet to debut). They're both web dramas so they're short and sweet and the music is awesome as well!
While the plots of She Was Pretty and Marriage, Not Dating are totally different, both shows give off a similar vibe. They're both rom-coms where the male lead is adamant about not falling for the female lead but slowly ends up doing so. The female leads in both shows are lower in status (than the male lead), and a little eccentric and over the top at times but, without meaning to, end up capturing the attention of the male leads. The chemistry between all of the characters in both shows is good as well.
In both Healer and City Hunter the male lead has more than one identity and works undercover alongside the female lead. The plots of both shows focus on uncovering and exposing the mistakes of the past and things end up being much more intertwined than they first appear to be. Park Min Young also plays the sharp-witted female lead in both shows. While I think the tone of City Hunter is slightly more heavy than that of Healer, the two shows are quite similar to each other.