When you take the "him" & "her" out of the equation and just put yourself in my shoes as a dude going on however many dates and I'm always expected to pay then it no longer feels casual/inexpensive to me. More like a chore and something I probably should budget for.
I hardly believe it's about income/affording the date. Rarely have I come across someone who thinks frugal is anything but a 4-letter word. They spend plenty of money going out and so I doubt that they are trying to all of a sudden be frugal wondering if they can afford the $7 wine ($14 in san diego). I agree that if a guy is just trying to test the woman then that's just weird/pathetic and not even helpful.
I think I'm just bitching about why I'm always expected to pay on dates. And since I'm wining please feel free to face punch.
Be more selective about whom you ask out. Ask out fewer people, only the ones you like a lot, know pretty well, and would enjoy treating to a coffee or even a meal. How many dates do you go on each month? Personally I think it's too much trouble to date more than a few times a month, max. I'm just not that social.
+1
If this is causing this much stress, I have to agree it sounds like you might want to focus on quality over quantity and cut down on the number of dates.
I'm surprised by how many people are willing to be complacent about being single, or take such a casual approach to dating.
Who you end up with is probably the single biggest, most influential life decision most people will ever make, right up there with having kids or not, and way way above what city to live in, what house or car to buy, or what career to pursue.
You wouldn't say "meh, if the right job comes along, I'll take it" - you go out and look for what you want!
Of course quality matters - if not, you could just go on one date, marry that person, and be done with it.
I've been on 36 first dates, but only 8 third dates.
I've met a number of people (including my ex-wife and one of the women I'm dating now) through regular life, school, work, fun events - but the majority are through the internet, for the simple reason that quality and compatibility matter.
On OKC I can filter for stuff like politics, religion, moral values, education, smoking, whether she has kids, whether she wants kids, frugality... not to mention if she is even single, and if so if she is looking for something serious. How do you filter for all that stuff at a party? It saves a whole lot of time. And then, filter applied, I can read her self summary in text, and decide if I'm interested enough to write her, and then she can look at me and filter and save us some time, or not and we meet up, already knowing we have at least a little more in common than just mutual friends or a single shared hobby or interest.
And even after all that, 1 in 4 neither of us is interested enough for it to go anywhere.
I just keep getting older and older, while still being single, so to some extent it becomes a numbers game - if I made a point of going on fewer dates, just to space them out in principal, or to save money, it would just take that much longer to run across someone compatible.
The suggestions for dates that aren't dinner or drinks are good though. Some of my best dates were at her place, or meet at farmers market, go back to my place and make lunch with what we bought, or a hike in the woods. But for some reason most people always want the first one to be at a restaurant.