I got a story about Theo.
So this is right afterthe Cubs sign him, so naturally his contract size and length is the hot topic in Chicago sports circles. anyways, a buddy and I go out on a Wednesday night and just get trashed. To end the night we go to this hot dog joint famous for its Chicago styles, A place called The Weiner Circle. The Weiner circle is a place where you cuss and be rude and be vulgar to the staff and they are back at you. They have this thing called a chocolate milk shake....from Wikipedia, Customers commonly request a "chocolate shake," which is code for asking one of the female employees to shake her....yadda yadda yadda.
Three guys and two girls come in, suits and ties and party dresses....I'm not thinking anything of it. A 4th guy, not with the group hands me his phone and asks me to take a picture of him with One of the suits.
I take the phone and as I hand the phone back I ask, a little bit too loud, "Who is that?." Loud enough for Theo can overhear.
So Theos buddies are getting food, we just kinda sit in the back and chat. No baseball talk, turns out he had some function with some lawyers from one of chicagos big firms, Kirkland and Ellis I don't know. They were hungry and wanted food.......so we're there and Theo reaches in his pocket and grabs a $20 and asks me "what I think" while flashing the bill. I smile, and say "sounds good". The wait is so excruciatingly long that he puts it back in his pocket to which I say "I think you can afford it." He looks at me seriously, smiles then just laughs, "your right, pulls the 20$ back out....
Tldr: Theo Epstein ordered milkshakes.
I know I have ordered many milkshakes myself...don't remember any of them, though.