Compliment and opinion forming

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Anyone else really struggle with this?

To give you an example someone on facebook who regulary sends me pictures of themself in regards to a recent acheivement, in this case an award ceremony (nothing lewd before you ask) and asks me non specific questions like 'what do i think?'

In this situation i dont understand if they are fishing for a compliment about their appearance or an opinion about the context of the picture.

Ultimately i chicken out and respond with something between the lines. I am afraid of offending this person.

Does anyone else know what im talking about?

Yup - and it's 50/50 deal - or something like that - I miss half the time, or there abouts - I haven't really added it up. I think a vague answer might just be a good response to a vague request. I think the less said the better and then they can, and will, fill it in. I just say, "whoo hoo" or something - seems to do the trick. It seems they want a "whoo hoo" for something. If that's between the lines, well, that's what I do. Thumbs up, "whoo hoo", "great", "wow". I just grab one out of the bag. If I say more and I'm wrong, well I'm told pretty fast and I just say, "Well, I don't know". Lots of times they think I'm goofing around - oh, well.

I always just reply with what I think. They asked me what do I think, don't they?

In your example my answer would be something like "You look good/bad/moderate in this picture, and picture in itself is good/bad" And maybe I give some explanation - why I think it is good/bad.

If that person is angry with me after my answer(and it happens a lot, yeah) I'll reply that if he/she do not want a honest answer then they should not asks me. And that he/she can always count on me, that I give honest and neutral opinion and that if he/she want some flattery - he/she should go somewhere else.
Some appreciate it. At least they know, that when I say that something is good - I really mean it.

It depends. If it is something asked of me in person then I would ask them to be more specific. If it's online then I would craft a nice response that I think they would want to hear, even though it may not be what I think or what I want to write. At least that's what I think I would do. I don't use social networking so it's hard to say for real.