Deciding who should be paying for things in a relationship is always tricky. It feels pretty unromantic to Venmo a date $16 for sushi, even if it's technically paying for exactly what you ate. Many couples have a "I'll get you this time, you'll get me next time" dynamic that is usually pretty healthy. That works well when couples have similar incomes. If you're both making $55K a year, there's no reason the man should be paying more just because he's a man. On the other hand, if one person makes $200,000 a year and the other makes $35,000, the higher earner probably covers the "fun" expenses, especially if they are the one insisting on going out and doing a bunch of fun, expensive things. You have to be open about what you can actually afford with your partner, because nobody wants someone to be sweating over the price of two movie tickets and dinner afterward.
Some people try to plan dates that cost as little as possible. I'm friends with a couple obsessed with this coupon app that lets them eat $100 meals for $50, and although I probably wouldn't do what they do, I have to respect their grind. The thing about using an app like that, or any other kind of restrictive "deal," is that you both have to be in on it. If you knew you could get a $100 meal for $50, you'd order very differently than if you thought you could only spend $25 on dinner.
The guy in this story is one of those people who loves to use his credit card points. He thinks getting $400 back from the credit card company on restaurant purchases is a great deal, even though he pays nearly $1000 a year to own the card. His card use isn't really the problem. The problem is that he's mad at his girlfriend for wanting to order a $60 steak when they're getting $100 off their meal.