wow, what a great thread :-)

i think that the 'gut feeling' or 'gut reaction' that people are talking about is hugely linked to emotion. this might be more controversial than i think it is, but i guess i conceive of 'feeling connected' as something along the lines of 'emotional attunement' or 'empathetic attunement' or 'resonance'. I think it is easier to describe that in the case of infants...

infant is feeling warm and happy and smiles at mother. if the mother responds to the infants smile with a smile of her own that is genuine that is an attuned response.

therapy analogue: if you are telling your therapist about something you are really proud of or happy about and you smile as you are reporting it then if the therapist responds with a smile / happiness / pride of her own that is genuine that is an attuned response.

not attuned analogue: therapist says something like 'oh i did this' (shifts the focus to their achievement) or says 'but that wasn't so great after all' (looks disapproving or something) or says 'but you could do this next time' (is dismissive of the achievement).

infant is feeling upset / disgruntled / frustrated / irritable. an attuned response would be to comiserate / soothe. a not attuned response would be to shift the focus to oneself or undermine the feeling ('there is nothing to be upset about just get over it) etc.

I think the feeling of connection is based on attuned connections to others. In therapy it is mostly about the therapist empathising with our mood and thereby matching their mood to ours in an attuned way. IRL, however (outside therapy) friendships are based on reciprocal attunement.

For example... In order to experience emotional attunement with people you need to spend time with them. Going out for coffee or going to movies or spending time with them in class or whatever. What do people want? Moments of emotional attunement. I have some friends who are into movies and I quite like them myself. We all get a bit excited before the movie (emotional attunement) and then after the movie we recount some of the scenes and the like. Or I quite often go out for coffee with people and we talk about how our work is going (since we all have to do roughly the same thing). Sometimes we are attuned with each other because we are both happy with our work or because we are both a bit down about it. Sometimes I'm doing well and the other person isn't but I can comiserate with them and encourage them along. It takes effort (it can be quite draining) to empathise with others and allow their experiences to affect us so our mood matches theirs. That is where relationships are supposed to be reciprocal. When someone is attuned to us it can kind of 'refuel' us even though being attuned to them can (at times) require quite a bit of effort.

I think that friendships are really based on how much one can interact with the person fairly naturally (so it isn't that you have to focus on them all the time and that you have enough in common for pleasant experiences where the other person helps amplify them into a happy experience). and good friends are people who you know you can call on when times are tough and they will be able to comiserate with you and help you feel a bit better.

it is hard though...

sounds to me that with this guy... something upsetting has happened to him. he does like you because he really went out of his way to reach out to you. and now... sounds to me like he needs a friend. i would txt him and say 'i'm sorry to hear that this has happened. would you like to go for coffee (or something)?' he might be grateful to be distracted from it or he might be grateful to talk to you about it. sounds like he needs a friend to be soothing right now. and so... it is up to you whether you consider him a friend or not and if you do consider him a friend then it is time for you to step up to the plate and be a friend to him. that is how friendships are made / maintained.

it is hard though...