Is frugality a turn-off?

So, my boss gave me a $100 gift card to an upscale restaurant in downtown Chicago. Since I'm her assistant, she asked me for a restaurant that would wow her tough client and Yelp saved my ass. Earlier, I won two tickets to the Sears Tower's sky deck. I was telling my coworkers that I basically got a free date night thanks to the office. They all told me that if they found out that I used a gift card on the first date, then it's a deal breaker. I don't wanna go to an upscale restaurant alone :-(

What do you guys think?

Edit: autocorrect sucks

Edit 2: Return of the OP: I have a follow-up question, then. What do you consider being cheap, then?