I met with the misery of a broken heart.
Grief shows in your eyes by making them look like you've gone through a lot of bitterness and hardship. You can always see it in someone else if you look them in the eyes too.
This word uses the kun'yomi readings for the kanji. You kind of learned this reading for 憂, but not exactly. Here's a mnemonic to help you remember it:
The bitterness that shows in your eyes takes the rays (れ) of light out of them, leaving you with just the う part of the reading that you know. That's why this reading is just う and not うれ like the others.