What did these deep and meaningful conversations consist of? I'd put more stock in that than if she touches her hair dude. Besides, it sounds like you aren't really all that keen on fucking her. Maybe she picked up on that.
Not to be a dick, but I think you should spend some money on clothes. If you're 30+ and wear mostly tshirts, it's time to call Carson for a makeover. Asking a girl to go shopping is a great date idea btw - yes, buy her something too. Head for boutiques in the city imo, not some suburban mall. Grab a bite, decide where to go out in your cool new threads. Leave the changing room door open so she can have a look - she'll be curious. If things are going really well, model some underwear.

Just be upfront about the day's budget unless you're a millionaire.