I’m surprised guys still struggle with the question of who pays on dates. It seems to be a perennial issue that never gets satisfactorily resolved. There’s a simple solution that skirts the problem entirely — don’t take her on traditional dates that cost more than a few bucks.
This isn’t so much about saving money as it is about avoiding the impression that you are buying her approval. Although all girls say they like it when a guy pays for them on dates (some even demand it on principle), the reality is that she will subconsciously slightly downgrade your status if you are quick to spend on her. The amount you are downgraded is directly proportional to the amount and eagerness with which you pay for her company. A fancy dinner followed by dessert and cocktails that costs you $100 will get you no further with a girl than if you had bought her a single beer. In fact, it may even hurt your chances.
Leave the dinners and special nights out for girls you are already banging.
My favorite types of dates are ones where she accompanies me on a shopping excursion in boutique shops around the city. Consignment shops are great for showing my fun side where we dress up in retro clothes and role play. Cost of this date = zero dollars. My standard date 1 and date 2 routine is a chill lounge or dive bar on a weeknight. Drinks for both of us will run me $30 tops. Usually it is less because she will buy a round or two.
There is only one thing worse than coming across as a guy who must buy girls’ affections, and that is looking like a cheap fuck. Don’t make a big production out of deciding who pays for drinks. Buy the first round, but frame it in a way that elevates your status. A foolproof way to do this is to ask her what she’s having, and as you’re getting up to go to the bar to order, say with a grin
“I’ll get this round, and you can get the next hundred rounds. Top shelf liquor only, please. I have standards.”
A few words can send a lot of subtle messages. Saying the above demonstrates that you don’t really care who is paying, but you’ll have some fun with the situation anyhow. It also shows you are not buying her drinks to appease her and won’t be the type of guy who gets used like a walking ATM, yet still pays homage to human nature and the deep desire of women to see resource displays in the men they are considering for sex.
When you have lightened the mood like this she will enthusiastically buy the next round. Congratulate yourself. Getting a girl to buy you something, even a small thing like a drink, creates the feeling in her that she has invested in you, and therefore she will assume you must be worthy of her investment. When she buys you a summer home in Tuscany she will have no choice but to fall in love with you.