Yeah but typically that conversation comes after days of texting/calling to get to know them somewhat. It's not like I'm gonna match with someone and immediately ask them if they are comfortable splitting the bill on the first date. Maybe I should just ask that right out of the gate to avoid wasting time. Idk.

It's the constant lost progress that wears you down. You're carrying the conversation and keeping it fun while half the women are dry and give short answers to everything because they are messaging back the 20 other guys who all matched with them that day. So you put in the effort to try and stand out only to find out the night before a date or when a date is first brought up that they aren't compatible. It's just draining on you after enough times.