Folk Yes, I think so too. I have had a lot of similar 20-something year old messaging me. I am also 37 this year. 37... I do not know if there is a part of me that is indeed feeling quite old actually. I actually do not believe I am 37 sometimes. I am getting conscious about the photos and how I look, but I do not want to get all too paranoid about how I am seen. I need to stay calm, cool. Sigh. This is tough...
By the way, the way you described the "people pleaser" behaviour is very spot on too. 
I think I am like that a bit too, and that is where things fell apart for me. i.e. the distancing from those who I am supposed to be very close to. As I tried and chase somebody else and help them. In doing so, I neglect my own family or my own personal relationships. I realised I learnt to walk away faster than I stayed.
Jesy Don't do that... Gosh, you reminded me of myself when I was younger too. It's like, I start to have feelings and fall for someone, but then my "mother theresa" moment comes out, and it really confuses the guy. Plus anyway, he shouldn't tell you about his past. Maybe he needs to tell you just so you know how he has become where he is now, but surely, if you guys like each other, then you got to protect one another and focus on what you have got ? (Btw, I also just broke up with an ex as well, and in the beginning, I told him to find other girls. I even found a list of girls for him on okc, cos he was not treating me well, and I cannot be who he wants to be with ! He was really all over the place. That is just crazy isn't it ?) I can also say that, one of the more great guy that I let go off in the past had indeed told me of his past too, and I thought that there cannot be more than "the one" for one person, so I let him go ! That is just silly. So please, do not play with his mind, and just be there for him. Especially if you like him. Do not send him back to his ex. That is just silly.
Jarlin If you do like this guy an awful lot, then fight for love. So, remind him then of you also. Why not write something like "I understand that you need to help your friend, but won't you let me know when we can meet again?" Something nice, polite, but the important part is also, letting him know that you also want him as well, even though you have been understanding. If you put literally that you are understanding, then maybe he will "click". Cos at the moment, he may not have read it well.
It sounds like your uncle and auntie is getting giddy ! 
Bless.
KouignAmann Congrats ! 