Best way to raise Ashara affection is making sure you have her summoned for dialogue choices and choosing the ones she likes of course. She doesn't like many gifts UNLESS you romance her. If you're romancing a companion then they gain more affection from the gifts you give them. If you choose the [Flirt] dialogue options when you are speaking with her during a private companion chat on your ship she likes everything except Trophy and Underworld Good. Romancing your companion is also practiaclly the only use for Courting companion gifts. Stock up on those too, but not too many. Get companion gifts from crew tasks. I've been farming companion gifts lately and I've maxed out several companions affections. I used this chart to help decide who should get what gift and mailed gifts to my other characters who's companion would enjoy the gift more. http://dulfy.net/2012/04/22/companion-gifts-and-crafting-bonuses-for-1-2/ Some are hard like Ashara, she's an airhead. Others like Blizz for example are really easy. So don't give up. Another piece of advice, don't gift your companion all the way to 10000 because you will gain affection from the conversations you have with them.