Cute concept and I like the characters, what little I could see of them. A nice mix of luck and skill; more luck perhaps. The mechanic actually felt pretty realistic: I want to make her happy, but I'm limited by what actions actually occur to my socially awkward brain. I feel like a lot of the times I couldn't win because I just couldn't think of the right thing to do (didn't have any of the right cards). Is that what a real date is like? :3 I wouldn't know ToT. The fact that the affection meter caps at 100% means that even if you do really well for most of the date, if you have a bad hand at the last location, there can be nothing you can do.
I tried the Windows version because it was written that the web version was buggy. Unfortunately the window was too small and I couldn't find any way to make it bigger or go fullscreen, and the text was too small for my aging eyesight >.< So I played the web version, and while there are some graphical bugs, it seemed to work just fine. Sometimes a wild card appeared to be the wrong color, but mechanically the game always treated it as the color it was supposed to be.