Never. But only if you want to, A simple idea that many don't understand and mastering it, or rather mastering the appearance of it, would make your generosity either disgusting or sexy. and it is a simple, just by mastering the accompanying wording and geste, but before I have to declare, the amount is never important as much as the accompanying verbal text. I knew many he took women to five stars restaurants and wouldn't get as good as results as men taking their dates to an ice-cream joint. here are some basics:

  1. Which wording did you choose when you invited her? "I want to do "this" so if you're free, you can join?" or did you say, "I'd like to invite you to this restaurant? Here the first statement does not oblige you, but the latter does give the hint. However, I'd recommend, "I'd want to take some walk around $$$$$$ and later we could get a bite in one of the restraints at $$$$$$", spontaneous and non-obliging, and the act of generosity would be welcomed.

  2. opening the menu; you invited her, you should lead her on choosing the meal, women hate taking decisions, however they get all bitchy if you choose for them, therefore choose two or three options and add some bullshit like "I heard the salmon here comes straight from Norway from a lake preserved inside the peninsula from all oil extraction.. etc" whatever sentences to make her feel classy in one star restaurant.

  3. the golden sentence; the bill comes in, time to pay, she may offer to split, but your chivalry kicks in, you let her pay? not most women find it not sexy if the man allowed him to pay, so you got to pay it, but in the same way do not make it look like you're obliged to pay it, either else she may get the vibe you're expecting sex in return, that's pressure, women act against pressure. therefore, use your wording right, what I suggest, show no hesitation, smile and say:

    "I am happy you came out tonight, it was a nice time, no no, please allow me for this one, it would make me happy".

see, firstly, you signal you're happy, second, you asked a rhetoric permission, which signals that you're not under pressure to pay, and you showed initiative which is a masculine trait.

Simple quick idea based on wide observation I thought to share, what do you usually do?