Originally Posted by blackize
I'm wouldn't consider this.
What about something like a groupon though? Groupons are much more socially acceptable, and you can always spin it like I've been meaning to try this place so when they had a groupon a last week I bought it, care to join me? Or you can weave it into conversation at dinner like "This place is great, I never would have known about it if it weren't for their groupon last week" or "This place sucks, I should know better than to buy groupons for restaurants I haven't tried yet"
blackize - totally context dependent. If it's someone you've known somewhat and have an established comfort level, and now looking to date... I suppose this is OK, but even then (in a very favorable "use groupon on 1st date context") I'd personally avoid it. Very little upside (you save what, $40 at the most?), and pretty decent exposure to the downside (ie, she thinks you're cheap, possibly busto, and that colors her view of you).
In a vacuum, even the slightest appearance of cheapness can be a big red flag for women, so best to avoid on all 1st dates as a rule of thumb (imo).
And to clarify - some women do really appreciate frugality, which is very different from being cheap of course (and using a Groupon can easily fall in the category of frugality vs. being a cheapskate). However, that line between cheap/frugal is very hard to distinguish for your date the first time you go out.