The stigma of using a coupon didn't bother me so much, most restaurant servers were always cool about redeeming them (and of course I always tipped on the pre-Groupon bill.) But I would sometimes get an (unintentional) negative vibe from higher ups, like great another money-losing customer that I'll never see again. That reaction is what discouraged me from using Groupon, if it just ends up generally being a bad proposition for businesses I'd rather just avoid the whole thing.
Oh man, this reminds me I still have a much of credit at Restaurant.com, which I stopped using a few years ago too...