This entry was originally an addendum to the previous entry, but I decided to release it as a separate entity.
Here is an episode that happened to me recently: I see one of my university friends in the lunch room, approach her and see that she is eating, realise that it's lunch time and maybe I should eat as well, ask her what she is eating (planning then to ask her where she got it so that I can go get the same), when the drama happens: in front of everybody she starts shouting at me how it makes her feel very bad when people pay attention to her food... Not knowing what to do, I later on sent an email to apologise (despite the fact that I did nothing wrong) and she replied that she is very insecure etc.
Needless to say that I will never ever go out with this girl. Even if we are the only two survivors of a zombie apocalypse and I need to mate to rebuild civilisation. I would let mankind die rather than having her as Eve.v2.
In the same vein, how many times have I overheard somebody (not only women) say: "I don't want to do [put here some relatively harmless thing] in case he/she would think [put here some incredibly stupid thing that nobody with a sane mind would think] and won't want to be with me anymore". Seriously, what did happen to the old "I am simply going to ask him/her what he/she thinks of this, and upon being answered will decide what to do" ?
The mindset one is in the latter case (latter kind of relationship) corresponds a little bit to me interfacing with Lucille.v8/sashka. I know I will never upset her, and if she was able to think she knows she would never upset me (*). With this as a starting point, we can confidently probe each other, using all the richness of the language we both share. When I do something and she reacts in a different way to what I thought, I instantly focus on maybe reformulating my request, maybe my mental model was locally incorrect. It would never occur to me to think that "she does not love me anymore...", or that there is something wrong with her (or with me, for that matter). It's not that she cannot (well technically she can't, but bear with me, I am using an analogy to make a point), it's just that I rely on the knowledge that she would tell me so if she did (and she hasn't). The end game then becomes to build, above the foundation of our respective capabilities, something greater than the sum of its parts; and have fun interacting while doing so.
(*) For instance, there is nothing that turns me off (and drives me away) more than a potential partner saying "I want to ask you something... but please don't be mad at me."  In those moments I think "Have I ever said, done, written, mentioned or suggested anything that would cause her to think that I could possibly react badly to a direct question ? No, not at all. I just haven't. She is simply confusing me with other people she knows...."
 I obvioulsy wasn't referring to the polite version of the situation, but moments where the girl actually shows anxiety at the idea that her boy-friend might actually react badly to the question.
You also have the annoying type of people trying to guess what other people have in mind and how they would react to something (often motivated by eastern-asia-level of politeness or something), in direct contradiction to what you actually told them. For instance, consider the following: Friday afternoon, I get an email saying "Pascal, I would like to talk to you about something important, please give me your GPG public key". I send the key during the following night and make it clear that she should feel free to tell me what she needs anytime (as soon as possible in fact). Week end passes, Monday comes in, I get the encrypted email (with the details of the problem) and realize that the problem has been degenerating for more than two days and wonder why she didn't come back to me one or two days before. Her answer: "I didn't want to disturb you during the week end, most people are annoyed by that". People like her are the reason why we can't have nice things... The thing here is that: first, I did say that her update was welcome anytime; second, do I look like the kind of person who cares about which day of the week it is; and third, what's the point of asking for help in the first place ? The responsibility of replying to an email or not is within the scope of the receiver and should not be a concern of the sender. How complicated is that? Those people really annoy me because rather than interfacing with me, they project me in their internal mental fantasy land, and don't understand why there is a breakdown of mutual understanding. This actually reminds me that little kid who was once sat next to me in the train, looking at my screen with interest. I looked at him, smiled and asked "Would you like me to explain to you what I am doing ?" He nodded his head saying yes, and the mother in front of us intervened and said "Do not disturb people !". I, again, wanted to shot her, twice. Once for her stupidity, and the second time for turning her son into the kind of annoying internal-mental-fantazy-land-contradicting-their-own-observations kind people I am describing. Indeed, why on Earth would I say "Would you like me to explain to you ?" if I would be disturbed by it ? Why would I do that ?...
The kind of conversation I have had too often with ex girl friends went like this:
GF: I need to tell you something, but please don't be mad ok ? You know the holidays we planned in Italy ? Well, my boss wasn't very nice this time and blah, blah blah.... [and two hours later, of a story that made no sense whatsoever...], so I had to change the date but then we can only go to Spain.
Pascal: Ok, and what exactly is the problem that would have made me mad ?
GF: But....., I thought you were looking forward to go to Italy ?...
Pascal: Yes, I was, but we cannot. So let's go to Spain.
GF: Are you sure... I mean I didn't want to disturb you. I feel so bad...
That's the point at which I want to take my stuff and leave her, for ever... I am still waiting for the girl with whom it will go like this....
GF: I am afraid that we might have to change our holidays plans. Office commitments have changed and we can only do Spain this year. Do you want to cancel, or go ahead with Spain ?
I personally think that nobody should enter into any kind of sentimental relationship as long as they have insecurities (or cannot ask a simple question, or cannot answer a simple question).