The Painter of the Wind (2008)

1. Both dramas have Moon Geun Young's character having relationships with older men.\
2. Actually, the main reason I'm recommending Painter of the Wind is because it's such an underrated drama and more people need to watch it. Especially Moon Geun Young fans, Moon Geun Young showed superb acting skills in Painter and it is her work that made her receive a daesang and a baeksang award.
(Bonus: Park Jin Woo, Moon Geun Young's boyfriend in My Little Bride, also plays her same age rival student in Painter of the Wind).

They are both very similar.
The main actress in both is Moon Geun Young and she disguises herself as a boy in both.
They are both historical drama's and focus on crafts.
The Painter of the Wind is about a painter and Goddess Of Fire, Jeongi is about a potter.

Both dramas feature Moon Chae Won in hanbok (where she looks extra pretty). Even though her role in Painter is only minor, it's still worth watching because it's her breakthrough role and her role in it is so unique. She has chemistry in her partners in both dramas that led her to win best couples with her respective partners. Both dramas are really great in general (in fact both were nominated for Baeksang). As of February 2, 2021, these are also the only two dramas that got MCW to be nominated at Baeksang Awards.

Both have a stunning chemistry between the women and I also noticed that the pairs actresses from TPOTW (Two Moons I pertain to Moon Chae Won and Moon Geun Young) and The Handmaiden (Two Kims pertains to Kim Min Hee and Kim Tae Ri). They have similar surnames which I find it cute.

However, TPOTW has a tragic ending that's why I wished and waited for 8 years for a lesbian movie that defies South Korean stigma against LGBTQ.

Jewel in the Palace goes deep into Korean cooking and Painter of the Wind shows you traditional Korean painting. Both depict a really detailed image of the time period and both have a strong female main character. The romance in both is also quite mild and builds slowly.