Is it ok to ask people to reassure you about things when it’s not about whether they’re angry with you? For example, I never ask people if they’re mad/upset with me unless I’m asking sincerely and want a real answer. But I do frequently ask my friends if they think I’m ugly when I really just want them to reassure me that they, at least, don’t think I’m ugly (regardless of whether other people think that or not). Is that something I should stop doing?
realsocialskills said:
  
It depends on the relationship. It can be ok (and even really good) to do that with consenting people. What becomes bad is when you’re pressuring people into reassuring you who don’t want to.
  
There are definitely situations in which I want reassurance rather than advice or feedback, and situations in which I reassure rather than evaluating. 
 
I think it can be important to be explicit about what you’re asking for. Eg:
  
“Can you reassure me that I’m not ugly?” is better than “Do you think I’m ugly?”. It makes it clear what you’re looking for, and it’s honest rather than manipulative.
  
There are forms of that which can be, though, the words don’t make manipulation impossible. For instance, if you think someone is mad at you, it’s probably not a good time to say “Can you please reassure me that I’m not a terrible person?” At least, not without first finding out whether they’re mad and making it clear that you’re not evading the conflict.
  
tl;dr Asking for reassurance rather than evaluation can be an ok thing to do, if it is consensual.