When I think "Worst Dining Experience", I don't even really think too much about the food - all of my worst experiences were because of poor service or kitchen management. I expect there will be some meals we like and some we don't, but a hardworking, enthusiastic server or a manager on top of their game can make even a subpar meal enjoyable. Unfortunately, the converse is also true. My worst experience out of about 100 ADRs in the last 10 years was at California Grill in 2011. It was my 40th birthday dinner and I was there with my sisters and brothers in law - a table of 6. We went down during Food & Wine for a 5 day "adults only" trip, and wanted California Grill to be the crown jewel. They were very busy that Friday night, which is to be expected, but we were all in a good mood. We had been at Epcot all afternoon, so we were predisposed to having fun when we arrived. My sister even road the elevator up with Jon Schenider from The Dukes of Hazzard (who was there for his charity, Children's Miracle Network's, big weekend) - so we already had a funny story to share on Facebook before dinner, with all of friends asking important questions like "Did he drive there in the General Lee?".
We were seated in a section with a waitress who was clearly terrible at her job. Our waitress was a very heavy lady who had absolutely no personality, and was clearly having a difficult time both navigating the tables and keeping up with her 5 table section. It took over 40 minutes after we sat before anyone even brought water or bread to the table. I love wine, and since this was my birthday, I really wanted a couple special bottles opened and decanted right away so they'd be ready for dinner. I actually had to get up, go to the bar, ask for the sommelier, and have him get started on the wine, since the waitress hadn't visited our section. By the time she finally showed up, we were starting to get a little irritated, but determined to enjoy the night. We gently let her know we had been waiting a while and it was a special night, and also dropped the fact we had all waited tables before so we knew what it was like dealing with nights like this. Not even a smile from the lady. Over the course of the whole 2 hour meal, we had to flag down the waitress at every stage, to let her know when we needed plates cleaned, when we wanted to order dessert, etc. I felt like I was on the payroll instead of celebrating a birthday. Half the orders were brought out to the wrong spots, and one order was completely wrong, but we didn't even complain about it because we didn't want to wait another hour for the entree to be fixed. I really don't even remember what the food was like, as by then the experience was a total waste. I think my dinner tab that night for my wife and I was knocking on the door of $850, and thanks to TiW, I was forced to leave an 18% gratuity.
On the way out of the restaurant, the manager was at the check in desk and asked us how things were and while I at first just said great and kept walking, after two steps towards the elevator, I turned and let him know how unhappy I was with the service. He seemed apologetic, but really didn't offer much in the way of explanation for the experience. He did give us his business card and say the next time we were in town, to call him ahead of time and he'd make sure they made it up to us. The next day, one of my sisters went to use her credit card and found it was frozen - the waitress the night before had apparently run their bill through twice, and the credit card company had put a fraud lock on it. She spent 45 minutes on the phone with them trying to straighten it out, and then immediately took the business card and called that manager again to really lay into him. This time he stepped up, finding out that we had an illuminations cruise set for that night, and sending a complimentary cheese tray and a bottle of a very expensive wine that we had ordered the night before. It didn't fix the experience, but it did restore some good will.
I know bad experiences happen, but the fact this was such an expensive meal and on such a special night was very disappointing to us. I finally went back and tried California Grill again last summer, with much trepidation, and this time had one of the best experiences ever at Disney. Between the revamped menu and the fabulous waiter we had that night (a Morroccan guy named Tom), it was the hit of our entire trip. We even saw the same manager there and relayed the story to him, and he took a funny picture with my and wife and I so I could text it to my sister who had the credit card issue.
I worry about the direction of Disney Dining these days. Prices keep rising and with the advent of the "Dining Plan", I find what was once a dynamic and eclectic assortment of unique menus and flavors is becoming simplified, homogenized "high profit" fare, heavy on pre-prepared entrees and carbs. People no longer care about the quality of the food or the experience, they care about whether it is a "value" for their credits, so entrees which used to cost $15 5 years ago now show on the menu at $40, so a guest used to dining at Applebees can convince themselves that the dining credit they pre-paid $30 for is a "value". Not sure there is much that can be done to stop that trend, but my hope is that they at least continue to seek excellence in their servers and staff, as the commitment to guest satisfaction has always been Disney's hallmark, and goes a long way towards making the experiences "worth it" in the long run.