I have both ADHD and minor hearing loss that started when I was a teenager (wear earplugs if you frequent concerts and play in live bands, turn the music down on your headphones from max volume). It is a rough combo that led to plenty of awkward situations as an awkward teen.

The worst was when I was on a first date at a SixFlags and my date didn't tell me she was terrified of rollercoasters. I felt bad, but only went on a few rides without her and spent the remaining time trying to win a stuffy at a carnival game for her, trying to have a good time anyway. She was really really quiet and I was having a hard time with all the stimulus and crowd noise understanding her. Eventually, it got to the point where I was asking her to repeat everything more than once, so I started to autopilot. While we were waiting in line for something, she muttered something and I responded, my brain playing fill in the blanks, "Uh-huh."

Turns out, when I heard her say "Mumble mumble ride mumble bring mumble with you mumble." she was not saying, "I really wish I could go on a ride, but I am happy you wanted to bring me with you anyway!"

She was, instead, saying something along the lines of, "It must be so annoying that I haven't gone on a single ride, I bet you regret bringing me here with you at all today."

Needless to say, there was no 2nd date. She told me later it was shitty of me to respond like that, and I couldn't convince her that I just misheard her. Since then, if I can't understand someone after two tries, I just explain that I have bad hearing and need them to speak up. Asking someone to repeat themselves will always be less awkward than driving her home after that.