I Couldnt Stop Thinking About This Earlier - Tumblr Posts
I've seen a lot of people point out that while Astarion's whole "thing" in act 1 is that he's this sexy sweet talking savant, he only has 10 charisma and actually isn't all that good at it.
He practices cheesy pickup lines within earshot of the person he's going to say them to, and every single time he flirts with tav it's extremely heavy-handed and almost cringeworthy. It's pretty obvious that he's trying to manipulate tav, even if the reason doesn't become clear until his act 2 confession.
But here's the thing: Astarion never actually needed to be all that good at flirting.
He says himself that the vast majority of his "targets" were drunks and brothel-goers. People who never actually saw him as anything other than an object for their pleasure. They were going to go home with him no matter what he said. A few pretty words and his physical beauty would do the rest.
But Tav is the first person to actually view him as a real person, which is why it becomes so glaringly obvious that he's not nearly as charming as he thinks he is. Astarion tells them at the tiefling party that "every part of their body screams temptation" and their response is that he's "sweet" and "silly". They're not buying it for second, because they don't need to be told pretty lies to like him. They like him because of who he really is as a person. They fall in love with him not because he's good in bed or has pretty eyes or a sexy body. They fall in love with him because he's sweet and secretly very kind. Because there is so much pain and sadness and fear in him, and he truly cannot see how amazing he really is. That his goodness never really went away, it just got hidden for a while.