The eye rolling part, if you've not done so already stop that.

Awkward position to be in. Have had friends whose bands sucked, but I loved them and was very grateful to have escaped being asked what i thought.

I have a document which the FBI says I have to carry with me at all times which states "If this person jumps on top of a table and starts to belt out a tune, the person who shoot and kills him is directed to call the FBI and receive an award of $2. I do not sing. (that is a period) But if I did jump up on a stage or table and belt out a few I would hope for applause up until the time I pass. What the hell if I am going to perform I would hope for the illusion I am good.

Ignorance is bliss.

What harm is there in humoring her? I sing terribly but I sometimes do, anyway, just because it’s fun. Jackson Browne said, “Let your illusions last/until they shatter.” Take that to the bank.

it will probably hurt her more to know that you've been lying to her for 30 years then to know that you don't like her singing. Maybe just leave it alone.

You're right, to be kind to your friend, you are stuck maintaining this white lie for the duration of your friendship. She sounds like she enjoys singing greatly, so it shouldn't be too hard, I hope!

When I need to compliment someone, I try to find something I can truly endorse. For your friend, as she comes off her gig, instead of gushing about her (ahem) wonderful singing voice, what about something like, "The enthusiasm you showed on the last song - wow!" and "You blew me away with how much emotion you put into the opening number!" etc. etc. When anyone is brave enough to perform in front of strangers and friends, there's always something one can find to compliment them on.

That depends if you still want to be her friend or not.

Lying is such a dirty word...

I would tell her a qualified untruth until death do you part..

The real question here is am I telling a white lie to someone I am dearly fond of in order to protect and foster both the friendship and her feelings
..or...to protect the friendship and my feelings?

It's a grey area... I don't envy you..but the fact that she values your opinion does make it a little complicated...

This is a white lie. Doesn't sound like it's any skin off of your back. Keep doing it, you are clearly a very good friend and I can't see an upside to deflating your friend's fantasy. It certainly isn't hurting anything.

Tell her the truth. If your friendship is a strong one you will last it out.

I was just thinking of Florence Foster Jenkins. Lol. I think you are stuck. Be kind, it isn't hurting anyone or worth risking the friendship.

I'm stuck in a similar situation. I have a cousin who's dream is to be on The Voice. He isn't a horrible singer, just not great or even that good. He puts out covers all the time on FB asking us all to love and share. I want to be supportive of his dream but know it isn't going to take him anywhere.