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.
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Also not acceptable to pretend to discuss financial topics so you can use the date as a tax write-off... especially when you have just finished bragging about your success as a financial planner. (One would think, if you're that's successful, you could afford a simple lunch!)
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