I think of it as a way that I can try some places that I normally wouldn't get to try since the certificate brings the prices down enough that they get more into my price range.
Sure, you can get a 50 dollar cert at StripSteak and go and order 2 burgers and maybe an app or something and get it practically free. But, I could have a burger at a lot of places.
I don't order the most expensive things on the menu, I just order what I think sounds good and take the discount as a bonus.
Like Mix and Aureole. I would probably have never tried either of these places since their prices are quite high for what I'm used to. However, the certificates brought the prices of dinner down just enough so that it was more affordable for me. I enjoyed the food at Aureole, btw, but I did not care at all for the service. Mix was great all around, and yes, it was still expensive after the certificate, but worth it for at least once. The view is just incredible and the restaurant itself is beautiful.
As for StripSteak, we have used a certificate there maybe 4 times on as many trips and never been disappointed.