Is she really 'unsure' about how beautiful she is, or is she just wanting to know how much you like her? Been with both, and the insecure ones are a little more challenging, but not impossible!! Ultimately, she REALLY wants that TRUST, and LOVE, but somewhere along the line, she got hurt, and doesn't trust. Start with building the trust, and eventually she will come around, and believe!! She has to TRUST YOU, and YOU NEED TO BE TRUSTWORTHY!!!
Yes it is hard, because oft more than not, no matter what you say or how often you say it, the girl won't believe you and that can become offensive over time, especially if the guy is speaking from the heart and not just saying the words to see where they splatter.
Yes. Yes it is. After a point it just becomes tiresome. Women don't want men who are unconfident and have loads of insecurities - while men are slightly more lenient on this one but we have a limit too. A girl who always rejects compliments will become hard to deal with at some point.
Definitely I tried to flirt with my friend so I could date her but when ever I complimented her she took it as an insult. So I was destroying our friendship because she was so insecure. I finally just asked her on a coffee date and she explained why she was so pissed at me. Needless to say that was our only date. But were still good friends though I do have to remind her that the guy is telling the truth when he calls her lovely. She is not bad looking either she just has a terrible self image.
Difficult but not impossible. I get told by others that I'm handsome. I just say "thank you" and move on. Some of the time I believe it, sometimes I don't. I've been told that I've gotten glances / "a once over" by very attractive gals so I just keep reminding myself of that.
Having been that girl, yes. It's basically telling the person you love that you don't believe them, you don't trust their judgement, and that they are a liar. That's a pretty shitty way to treat someone you are supposed to love and trust. Being massively insecure like that damages relationships. Trust me, I've dealt with that drama and am quite happy that I learned to not let it destroy me anymore.