Sorry you are having a tough time. I understand the situation you are describing - people sometimes say things without meaning them that can really hurt. My wife (and myself to a lesser extent) have been reduced to tears several times due to people who should know better saying something that knocks your feet away and any resolve you had disolves completely and you end up crying your heart out. My wifes response has been to cry openly in front of the person who hurt her. Having witnessed this there is nothing more powerful than seeing someone burst into flowing tears and know you caused them - people tend to backtrack with apologies.

Which I guess is pretty much what happened to you, although you tried to hide your tears.

When you let him into your room was it embarrasement that made you not look at him? And when you said you cried a little more did you allow tears to fall that he would have seen then?

One things for sure it sounds like you are an attractive crier   

I no longer tend to think of it as 'doing well' - if you have a spell immediately after a heartbreaking event (like your breaking up with your ex) where you don't get upset it's usual down to a reduced number of painful jolts which bring the loss and sadness to the front of you mind. For me (and perhaps you) a sign that this is the case is when something does hurt you how easily the tears come back and you feel low again. On the plus side these do fade over time.

This crying event interests me because it contains a social aspect with regard to how you and your friend reacted to you crying.

It's interesting that even though this guy is now your best friend you were embarassed to cry in front of him - even though he has already seen you cry before. I can understand you leaving the situation initially because he was actually the trigger for your tears but it's interesting you felt embrassed about crying when he was looking to say sorry and comfort you. He would have realised you were crying and actually gone to your room to cry so in terms of being embarrased about crying you would not have been able to hide this fact from him. But, then you tried to hide the physical signs of crying by not looking directly at him.

It's difficult to say what I'm getting a here so hopefully I'm making sense - there is two types of embarrasement with regards to crying as far as I see it. People can be embarrased about admitting that they cry - a percentage of the population both male and female will flatly deny that they cry when asked, even though you are unlikely so see them actually crying in person they will deny it ever happens. Given that the vast majority of people cry on a fairly regular basis this for most is clearly a lie. I've seen studies that sugest 75%-80% of adult women have cried in the last month, and 95% in the last year. For guys it's much less but 45%-50% have cried in the last month, and about 60%-70% in the last year. Think of these numbers when you are walking down a busy street or sitting on a train/bus the majority of people male and female will have cried within the last year, and a good percentage fairly recently.

The second type of embarrasement is the physical signs of crying. These people can be ok admitting that they cry but they are embarrased about allowing any one to see them cry. Most people see themselves as being ugly when they cry (something you mentioned in your observation) - but this tends to be refering to the red eyes, red runny nose, sobbing noises and crying face (sorry TorNorth). Tears are not the first thing people see as being ugly. So, if you are a tears kind of crier there is an argument to allowing your tears to be visible. If you are a loud crier or the intensity brings some of the 'ugly' elements out then you may feel more self-concious but in my experience if you cry like this if front of people you trust they will be immediately protective and comforting and not think negatively about your emotions.

Women tend to experience the second type of embarrasement - they admit they cry but don't like anyone seeing them. Men tend to fall into the first category - they will say they don't cry at all, but when they do the tears tend to flow unchecked.

Anyway, long post and just an observation for discussion - no judgements either way but it relates kind of closely to your observation.

I think it's health to cry after your breakup and I think its better to cry with someone than cry alone - if the guy is a friend he will not care what you look like in tears (although he has already suggested you don't look all that bad) - he's a lucky guy I'd more than happily comfort you as you cried - and that's not just because of my little fetish