Longfellow: How drunk do I need to get!?

[=яενєηąŋŧ=]

So I've been trying to max relationship with Longfellow to get his perk, but I'm pretty much out of dialogue choices he like so it's down to chugging liquor as we're out exploring. I got his first conversation pretty early, but now it's been about 30 bottles worth of "Old Longfellow likes this" and I haven't gotten to the next "level" yet. How many bottles do I need to drink?

[Theo Hardmeier]

You dont really need to drink bottles....just travel and explore and eventually you will get to the next level.
Im not sure but maybe the shipbreaker quest is tied to it. Cant confirm though.