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sixes_and_sevens comments on Knowing what you want is a prerequisite to getting what you want - Less Wrong
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This is kind of tangential to the post, but I've ran into the same problem in my previous relationship as well. I value truth for the sake of truth, and I am often very blunt about it (I have since learned to be more polite/roundabout). Being polite, however, means answering questions like "Do you think that girl is prettier than me?" with a "No." regardless of what I believe is true. Doing that continuously hurt me, yet I've continued to do it because that's what my partner preferred. I think this is telling me that I value love almost as much as truth.
Yeah, this is exactly what I did too. I thought I was doing her a favor, but since then I've learned to be a lot more tactful in how I actually present my beliefs.
One might say being polite means not forcing other people to answer awkward questions.
Wow, you are right! For someone who is trying to be as open as I can, I sometimes forget that option. I should just say "Those kinds of questions make me uncomfortable, so I would really appreciate if you didn't ask them". Thanks!
Personally I try to avoid being involved with people who try to emotionally blackmail me into bolstering their self-esteem, but that's not a lot of help once you're already involved with them.
In that situation I'd probably try and turn it into a strategic joke by saying something like "Eugh, no...look at those horrible shapely legs and disgusting pert breasts; yuck, no way," or something to that effect. Bonus points for picking characteristics where your girlfriend has the edge.
Use this at your own risk. I take no responsibility for its efficacy.
To expand on this: the essence of politeness is to not consciously convey unpleasant thoughts, either by dodging communication on certain topics or by making use of subtext to convey them subconsciously (so as to avoid painful mutual knowledge).
A person X can, for example, turn an acquaintance Y down for a date by giving a proximal explicit reason, but do so in a subtly dismissive way that Y will subconsciously pick up on (and not ask X out again), and yet subtly enough so as not to constitute mutual knowledge of romantic rejection; Y may never consciously realize they've been rejected.
(Things get awkward when one party or the other botches such an exchange.)
Postel says you should answer awkward questions but not ask them. (Also, that you should say this girl isn't prettier than your interlocutor, but be fine when told she's prettier than you.)