Omg, you’ve just described my DS!!!
The bedtime feed has just got longer and longer and it got to a point where, no matter how long I fed him for, no matter how much I tried to cluster feed in the evening, he still cried in hunger when I took him off and put him to bed. He was then too worked up to latch and stimulate another let down. Frustrating for both of us.
Recently (at around 4.5-5 months), I got so fed up that I’ve started introducing a bottle at bedtime. I fed him both sides before he goes in the bath, then a bottle of formula before bed. I agonised over it for ages as, while he always had the very occasional formula top up, it was never a regular thing. I didn’t feel comfortable accepting that he would have one bottle every night.
However he was hungry and got too worked up to latch to feed further and the last feed was taking up to an hour - and I still ended up having to top him up anyway.
The bottle is working well for us and I’m now happy with our decision. I feed both sides before the bath to help keep my supply up (although I know that any supplementary feed will affect supply to some extent) and now he goes down to sleep happily, with a full belly.
Now, I’m not offering this as advice or a recommendation. I just wanted to share my experience and how we handled it.
You have my sympathies, even at 5 months, I still struggle with breastfeeding. It’s hard work! You sound like you’re doing brilliantly. The advice given to me was to just feed, feed, feed, to get your supply up, which I understand in theory. But when baby won’t latch again and is crying hungry, it’s hard to follow the advice even if you know it’s correct!
Can you express at all? Perhaps try to express after he’s just gone to sleep, then you could offer that extra breastmilk the next day as a bottle before bed? Just trying to think of a compromise which might help.