What is up with him? Why would he act like this?

sounds to me like he is a bit insecure. someone who says they need someone to love them (like he did) usually means they don't like them self (one who likes them self wouldn't worry about what others think of them). He is texting and flirting with you because he needs to know that someone out there likes him, he seeks approval from others to reure himself that he is worthy because he obviously thinks he isn't. he prob is a really nice guy but sounds to me like he has problems (like with work) and probably wouldn't be good boyfriend material. don't take it personally. if i were u i probably would step back a bit and not get too serious about him because after all i wouldn't want to be dating someone with "extra baggage."