Probably start with an icebreaker question, like
Why Jeff? Why do this to youself, and in public no less?!
The rest of my part of the convo would likely be some variation of this:
That should do the trick, he'd be eating out of the palm of my hand in no time, and ready to just say NO to Section 702 ;)
Dude has fuck you money times 5 more fuck yous. That's what those clothes and sunglasses say.
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Not to me. You can get that basic 70s outfit at a second-hand shop. To me, it just makes him look like a try-hard AFC douche canoe trying to "peacock". To each their own, I guess ;)
Oh I didn't mean cost wise, but overly flamboyant haha
Yup yup... like an AFC, peacocking ;)