There are a lot of Taiwanese dramas that fit your descriptions. Since I love this kind of plot as well, so I’ll recommend you my top 5:
1. Autumn Concerto (Taiwanese)- ML is a rich playboy who fell in love with a kind hearted and innocent FL. At first, he pursuit the FL only because of a bet, but later fell hard for her. Since the ML has abandonment issues, he has trouble trusting people hence would sometimes end up hurting the FL because of misunderstandings.
2. Loving Never Forgetting (Taiwanese) - This one is like Autumn Concerto. ML is rich and FL is kind and innocent. They had one night stand and the FL got pregnant w/o ML’s knowledge. They later crossed paths again after ML accidentally met his son. He hurts FL, humiliates her but end up falling for her.
3. Lavender (Taiwanese) - this one’s an older drama (2000/2001 I think) but worth watching bc it meets your preference. ML and FL meets when they were young but got separated. When they’re in their 20s they meet again but got tangled up with misunderstandings along the way so ML ends up always hurting the FL’s feelings.
4. Mia Tuan/ The Illicit Wife (Thailand) - this one is gonna be so hard to watch but if you want to feel that satisfaction that you’re looking for you need to watch this. You’ll get the ML begging for FL’s forgiveness in the end, this is it! The ending is so satisfying. TW // rape
5. Love in sadness (Korean) - The male lead is MADLY in love with FL and is overly possessive of her.TW // domestic abuse
Some bonuses you probably already watched but I’ll leave it here anyways:
Meteor Garden, Sawan biang, Playful Kiss, Boys over flowers, Well Intended love, Autumn Tale (2nd ML’s part), Devil beside you, why why love, general and I, secret, que sera sera, innocent man