I have been wondering lately, what do the words, "I miss you," actually mean?
I get confused sometimes because there are so many contexts.

Thank you, Dictionary.com :
miss1    
[mis] Show IPA
–verb (used with object)
1.to fail to hit or strike: to miss a target.
2.to fail to encounter, meet, catch, etc.: to miss a train.
3.to fail to take advantage of: to miss a chance.
4.to fail to be present at or for: to miss a day of school.
5.to notice the absence or loss of: When did you first miss your wallet?
6.to regret the absence or loss of: I miss you all dreadfully.
7.to escape or avoid: He just missed being caught.
8.to fail to perceive or understand: to miss the point of a remark.

When someone who I haven't seen for a long time tells me that they miss me, I wonder if they are just saying that because they don't really know what to say. The thought of, it's been a while, maybe I should say something and see how they're doing.
It's almost like that person doesn't actually care to see you or visit with you anything that may result when the feelings of "missing" arise. It's just like a guilty thought that slips out and creates less of something than not asking about them at all.
In that sense, I almost feel like every definition could apply to one use; one specific context cannot be dedicated to one particular use.
For example, my friend said they miss me. They haven't really tried all that much to contact me. They don't generally continue a conversation once its risen. It takes a lot to make plans and when they finally happen, they usually are quickly cut off because something else is waiting for them somewhere else. So, that person has failed to hit or strike; failed to encounter, meet catch; failed to take advantage of; failed to be present at or for; noticed the absence or loss of; regrets the absence or loss of; escaped or avoided; failed to perceive or understand.
I wonder how I have used this phrase previously and how the person has perceived. Well, they probably didn't pick it apart like I did, but may the next time you see someone name pop up on your buddy list, you go through your contact list in your phone, or you have a silly reminder of an lover or friend, choose your words wisely... or don't choose them at all.
Sometimes things are meant to be left where they are. Sometimes we can't patch up because there is nothing to patch. Sometimes we MISS the idea. We MISS the opportunity and try and play catch up. We MISS something that we final realized was real and somehow let slip away.
Simple, a MISS FIRE.
Well. Sometimes we learn the most from those.
Happy rainy day, cheers.