A few years ago a bunch of girlfriends and I were having dinner at
Indigo Grill and the conversation I remember most was one that has sparked many a heated debate since - is it OK to use a coupon on a date?
My answer: Absolutely not on the first date! However, there are tactful ways to do it from the second date and on (although, truthfully, I would wait for at least date three).
Groupon has done a lot to change the perception of coupons and make it much more socially acceptable. Thanks to what they've coined, "collective buying power". And thanks to a dozen or more copy cats you can find something fun, exciting and affordable to do almost any night of the week!

Sites to check out -
Groupon
Living Social
Local Twist
DiscoverSD
SignonSanDiego's Daily Deal
San Diego Magazine's Deals & Steals
How do you broach the subject with your date - tactfully? My suggestion would be to casually mention that you grabbed the latest deal and see if she has any interest in checking out this new restaurant, gondola ride, art museum, hot air ballon ride, etc.
Depending on how adventurous your date is you may want to scope out your plan prior to the actual date...We all know how Date Night's can go awry.