Questioning Looks

I know there is an age gap. It was a shock when I first knew. I'm not sure how I feel. There's something about him; maybe his innocence, how he treats kids, his lovely smile, his kindness....I'm not sure.
Sometimes I feel we communicate through our eyes; how we exchange looks like we are having a conversation. I then feel like he must be feeling there is something inside me for him. Maybe he's not sure, which makes sense as I don't even understand what I feel towards him, but he must be feeling there is something.
Sometimes I feel like he is thinking about it; that he's considered, even though he sometimes ignores my looks...maybe on purpose because he is not sure that what he is thinking of is true...maybe because he's not interested. I don't know if my analysis is even true. Maybe he never noticed in the first place.
I gave hints. I did some signs on purpose to grab his attention, several times. I believe my looks say a lot. I felt he could translate them that last day I saw him before I disappear for a while. He gave me that long questioning look, as if he's wondering about what I want from him and why I keep gazing at him for long times. But his look had a lot more than that, I felt like it had some sort of feelings; maybe something that he doesn't understand that is attached to me and my looks, and it also had some sadness in it as if he felt at that time that he would not be able to see me for sometime. It felt like a farewell look.
I felt bad then and it affected me a lot. Then, I got consumed in many work problems that my pain overwhelmed that. However, when I came back and saw him again, I felt strangely happy like a naive child. I am attached to this feeling as if I want any shelter from my pain...I want to take a break and feel these beautiful feelings.
That smile he gave me when we met after that long time was the most beautiful smile I have ever seen...a welcoming smile. I loved it.
Sometimes I can see the question mark in his looks. I totally understand how confused he is. But I'm wondering if he feels anything at all. He gave me that other look for few times that I remember well; longer look that had some feelings...but I'm not sure what kind of feelings. I believe he can see even more barriers that those I know of. He thinks I'm a married woman with kids, that there is an age gap, that he is not thinking of commitment as he has still a very long way to go...maybe even he's into another relationship.
I know it's naive and complicated. I cannot even translate this. It makes me feel silly. However, I need to go on with this between me and myself because I'm so frustrated and depressed. It's my way out of pain, self-punishing, sorrow, depression, and frustration. I need these feelings even if I'm just imagining them. I know it will not be except another failure painful story if I will keep digging deeper into this knowing it will never work out. However, I cannot stop. I need to go on. I like this passion while waiting to see him...that moment when our eyes meet...the smile that he brings to my life. I'm currently attached to this...at least till I get out of that terrible mood or maybe meet the right person, if any.