He seems a bit needy - women don’t like to constantly have to reinforce that she loves him (she’s not his mother) - seriously he would be better off not to ask and go down the pub - she will be all over him once she knows she has to work a bit for his affection.
Either that or she has already moved on! Either way the dude has to man up and have some self respect!
“Women don’t want needy, they want a colonel, a kaiser, a czar.”
-George Costanza