If she said he was too controlling, and it turned her off permanently, doesn’t engaging with her “assertively” in this manner just continue to demonstrate that he’s pushing his agenda and making boring “dates” to control the evening with his questionnaire to get laid? You know he’s doing a nice couple of things and then leaning in expectingly for a kiss like he ‘earned it’ and being all sulky when she doesn’t feel grateful and responsive. Money was tight, he acted like every grocery store purchase was a calamity and checked every receipt like she was his employee, and now she’s done and he doesn’t understand how she sees him. She understands that he feels like he outranks her in life but should feel affection for him too! So…no.