I've been improving on overcoming approach anxiety, but my main problem is when I talk to them, it's like a lot of small talk. Nothing of depth. For example, I was talking to this one really attractive girl as I was walking with her to some restaurant. I talked a lot about classes (we're both college freshmen) and where she came from. I had her guess my ethnicity (we're both Asian) and I guessed hers. I asked her a lot about her career aspirations and personal interests. I asked her what she'd be if she could be anything, and she said she'd be a fashion designed (I complimented her on her ability to dress well.) I told some stories about myself. Honestly, it just didn't feel like we were getting into a deep personal conversation.

Another important thing is that I felt like I wasn't really making enough jokes or making her laugh enough.

How do I work on this?