I think it’s important to see these communication styles as something to negotiate, rather than there being better and worse styles. Often these discussions are phrased as if women have to teach men to communicate, when I can see problems with both styles, and I think both can teach each other how to communicate with each other more effectively. In my case, I had to learn to be more sensitive, but I also had to teach my wife to be more direct (both in a respectful way, of course).
When it comes to questions like “How do I look? Tell me honestly”, it’s important to go over this genre of question in theory rather than confronting it in the moment. Not everyone does want affirmation. Personally, I know very few women who would hear that question from their husband and say “you look fine” even if they don’t think so. On the other hand, particularly if my wife asks me how she looks, I have to take into account that she may have spent quite a bit of time and money to look like that, and she has quite a bit invested in the answer. I make sure that I often complement her on her appearance and notice times when she has made an effort to look good, without being prompted. There are also ways to be honest without being hurtful – “I think this dress would look better on you” sounds better than “this dress looks bad on you”. I do sometimes critique what my wife is wearing, and she does the same with me, and neither of us leaves the room in tears because we’ve both discussed what asking that question means to the other person, and the response we are going to get if we ask it. It isn’t a value judgement on the other person, you’re trying to help them to look their best. As always, I’m describing what we negotiated, not the one right way to do things.
When it comes to other issues of subtext, body language etc., we have something similar. If my wife says she’s fine, I understand this to mean that she wants me to think she’s fine. If she’s not fine and she wants me to know this, she needs to use other words. I won’t keep asking whether something’s wrong (OK, maybe once). This is important to me, although it’s not that I can never pick up on times when she’s upset without saying anything. The fact is that other times I won’t see it, and in any case it’s important to be open about it when you’ve been offended by something that the other person did or said – that’s how people learn not to offend each other. On the other hand, I do need to be sensitive to times when I could be offensive, and be receptive to change things if I do learn that I’ve done something wrong rather than waiting to be called out on it every time. Empathy often requires people to listen to the other person talking about their emotional reaction to different events, because it’s often different from what our own reaction would be. After a while you develop an intuition for it, and a glance is all you need to remind you of a conversation you had earlier.
I would say that this requires trust on both sides (I’ll use the stereotypical male and female roles, but this dynamic can take place in different combinations and it’s not been one way in our case either). She needs to know that I am receptive to hear what she has to say – if she gives her honest opinion, I will take it seriously and not betray her trust. I’ll listen to hints and simple requests, so she doesn’t feel like she needs to nag or emotionally manipulate me in order for me to take any notice. On the other hand, I need to trust that she respects my autonomy, and that she’s not going to try to control me or get upset if I choose to do something different. In the same way, if she asks me for my honest opinion, she can trust that I will give it, but that it will be constructive. In turn, I can trust that an opinion offered in this spirit won’t get a negative response.