> I got stuck on the same part, and I mapped out every single one of the possible answers, and then went in order, one by one. Yes, this sounds like a drag, but it's what worked for me.
>
> *****spoiler***
>
> I do remember that he cracked when I asked the fourth question (can't remember which it is, but it was the option at the bottom when I started the interview). That is, I got a response when I asked this question:
>
> Start:
> 1st question
> 2nd question
> 3rd question
> *4th question
>
> then, I chose the second option (ummm,still following me?) out of two, then the first option out of 3, then the second, then the third. Hope this works!

*

I myself just finished this section, and I did so by mapping the responses. I feel that it might be helpful to clarify the above spoiler... the "Fourth question" is the "picking up chicks" choice between beer, TV, partying, and chicks. Beyond that, you have to find the path that gets you to the "beer thread" of the conversation. If you've been mapping, you'll know which one does this, and once you get into the beer thread, try the different options. At one point, you'll have a retort choice available that isn't an option when you start off talking about beer directly. Use this and you're home free.