Yes, it does sound like he's begging for you to ask him what's going on.
Maybe you can just reply with a "that's good" or "glad you're doing well".
That way you acknowledge his message, but don't appear overly eager.
My h would do that by text every once in a while. Eventually, when he realized that I wasn't going to come out and ask him, he'd just come out with what he wanted me to know.
M36 XH34 M-5 T7 4/11 H confused 5/11 ILYB 6/11 OW discovered 7/11 I move out, OW over 5/12-OW2,done->new EA, but H wont file 9/12 H "best bf ever" to EA/OW3 3/13 H/OW break up H files 4/13 D 6/18/13