If he feels the need to discuss it he is tacky anyway.....
First impressions are lasting and never can be repeated so if you feel taking me to olive garden is fine for a first date then okay. I wont be calling you back, not because of the cost of the meal but Im 99% sure I would have told you I hated that place.
I don;t care if you take me to a $400 dinner I will never feel like I owe you anything and I could care less about your expectations. That sound like one of them " I aint never had enough of nothing blues' type asshats and I will pass on them too.
Taking someone out should not feel like a favor or either side, but my time is valuable to me and I choose wisely on who I care to share it with. If the woman you are dating thinks a free meal is a "win" then you should raise the bar on your standards.
If you genuinely enjoy each others company it doesnt matter if we are drinking beer and eating a hot dog at the baseball park or chatting it up over a steak at Mortons. I would rather you find a nice out of the way restaurant with good reviews on Yelp versus making me feel like I can only have the 6 choices off the dinner for 2 special.