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Some of it may be how big his mouth is in relation to your breast. When I had LCs showing me, they told me to be patient and wait for him to make as big a mouth as possible. THEN, literally take the back of his head while his mouth is open and shove him to your breast as fast as possible. And if that's not comfortable, gently unlatch him by sticking a finger in his mouth to break suction and try again. I hope this helps? It's tough -- hang in there.

ETA: Depending on how much breast tissue you have, grab your breast with one hand and kind of hold it like a sandwich. Position it so that it's parallel to the angle of your LO's mouth. Not sure if that makes sense, but you want it to look like he's taking a bite out of the breast "sandwich." Then gently let go when you feel like he is latched.

Make sure your LO is going to the breast with his chin first and not tucked in (kinda like his head is tipped back). My girl used to tuck her chin down which forced her tongue up rather than out to cup the breast.

Also, make sure you're comfortable and well supported with a footrest if necessary, position baby so that he's tummy to tummy with you, nose level with your nipple and bring him up to your breast rather than leaning down to him.

If you can get back to basics then I'm sure you guys will get the hang of it!

This is the link I mentioned. It talks about a lip tie, but it's good for any shallow latch. @Kemma: your links are great, too. I think my LC sent me latching checklist one, too.

http://thefunnyshapedwoman.blogspot.com/2011/03/introducing-maxillary-labial-frenulum.html

@mrsjazz: that is a GREAT article! My LO had both her tongue and lip tie clipped at 7-8 weeks respectively and it was actually having the lip tie cut that helped us the most. I was particularly interested in the paragraph that mentioned lip tue babies leaving teeth indentations in the breast which is exactly what my girl does at almost ten months old.

@rahlyrah: since my LO was getting bottles from day 1, he was pretty lazy about opening wide. He didn't really have to with a bottle, it just got slid in. So I started making him open really wide for a bottle, which gave him a better latch on the bottle too. It helped a little. It was kind of frustrating though, because all I wanted was to get the bottle in his mouth as quickly as possible so he'd be happy. We also did the same kind of thing with a paci, just tried to coax him to open wider.

Good luck I promise it'll get better soon! He's growing and you're becoming a breastfeeding expert, it's just going to click soon! (Please don't punch me for saying that, I know I wanted to punch everyone who said it would just click but it truly will, especially as his mouth gets bigger and he gets better head control.) I'm rooting for you and rahlybaby!!

I remember having to literally drag my nipple down from LO'a nose and across his mouth to get him to open wide, and smoothing boob into his face, basically, with my hand like a "c" ... It takes a little practice, and sometimes I had to relatch him a few times before it would stick.

Also, I'm not sure if you'll find this helpful or not, but I feel like a lot of the advice says that your baby should have more of the aerola UNDER the nipple and less above it, which didn't actually work for me because my nipple ended up not going far enough into his mouth, so it was getting that squished look that was painful! Once I adjusted his positioning so he was more centered and taking the whole thing in evenly, it helped a lot.

Also, when we were first learning to latch correctly, I constantly had to pull his bottom lip down once he was latched on, to fix to the latch. Eventually, I stopped having to do this.

How old is your baby? It may also just naturally get easier and better when your baby is bigger and has a bigger mouth and can take your nipple in farther!

@rahlyrah: Yay! So glad to hear that it's getting better. Keep up the great work. It will get even better when baby gets a little bigger and starts getting better head control.