Hi rachel351 :
My advice is to Take Space. I know that you did over the Christmas holidays and that he contacted you and you started up communication again, which is fine, but I would not start doing more than is called for or going above and beyond for this guy.
The fact that this guy cancelled on you a few hours before your coffee meetup simply confirms my initial suspicion that he has commitment issues. Commitment phobes are notorious for cancelling plans or not making plans at all. They find it difficult to commit to anything, and anything which makes them feel locked in or tied down makes them feel claustrophobic and they want to head for the hills. This is just my guess, but I am guessing he could feel the concern and emotional investment from you and this made him want to back off. Commitment phobia can arise for a number of reasons, but these are not for you to figure out.
I think many of the posters on here are being unnecessarily patronising and harsh – it’s understandable because it’s frustrating to see someone making what you perceive to be the same mistakes over and over again. But it’s actually more subtle and complex than that. Many of the posters are implying that you have an agenda, as if the only reason you could want to show compassion and be his friend is because you hope to reconcile, but this is not necessarily the case. It is clear, to me anyway, that you like and care for him as a person, on top of whatever happened between you. It is very natural and understandable that you would want to be there for him. You seem like an empathetic person as well, and it is clear to me that you want to help.
Unfortunately, you cannot help. You can offer your friendship and support, but that is it. And if you are determined to have him as a friend, you need to take care to treat him the same way as any other friend, having proper boundaries in place, proper rules of consideration, and not having any undue expectations. I strongly recommend that you take a step back and determine what your own motives are and whether you are truly ok with just a friendship. You need to be honest with yourself. Seeing him as just a friend will protect you from getting overly invested. If you have hopes that things will rekindle between you, you need to be aware that whatever issues he has will not resolve overnight, and that it will probably be years before that is a possibility, if it happens at all.
So my advice – no, do not reschedule your coffee date of your own initiative. You should not have to work so hard to spend time with someone, depression or no. Let him reach out to you. And if he does (when he does) conduct this friendship on your own terms. Don’t get overly invested. Protect yourself. Listen to him, but don’t be his therapist or his mom. He’s a grown man and he needs space. And I would figure out, from your point of view, what you hope to gain from this friendship. If you just want the pleasure of his company from time to time, then great. But just make sure that you are not overly investing emotionally or trying to rescue him. And bear in mind that, if you choose to be friends with him, this is who he is. Someone who is prone to depression and anxiety and pulling away for periods of time. You can’t blame him for being this way – he has show you with ample evidence. Just make sure that you are ok with it.