I mean look, at least he held her hand without freaking out about it, at the end of this date, 82 chapters in. That sort of seems like actual progress, although we're still in 'pretend mode' so it doesn't REALLY count... more like 'holding hand practice'.
And the girl he loves is still going on multiple dates a week with other men. Jesus christ, this manga would be so perfect for like, an NTR sidestory that shows Mizuhara gobbling cock during compensated dating at every opportunity while this beta nerd keeps doing his cringey shit.