Creating The Best Winter Date in Chicago

[@tannerdow7566]

Dave’s crooked hat kills me

[@Jenniferscratch]

😂

[@cpm4778]

Middle school swag

[@lovejones72]

“Ventured away from the south side and west side a little” 😂😂😂

[@J-Albz]

This content was great. Alyssa was great. The guys were great. Genuinely a great video all around!

[@tylertrevino3]

Eddie is the fucking Rizzler?!

[@cmust17]

Always has been

[@CHIILTS]

Eddy is so smooth with it, absolute rizz machine

[@adamlewis5988]

This was funny. When the gift exchange happened and the employees thought it was the most genuine content barstool has done, this is.

[@chogers24]

eddie brought his robe on the date lol

[@MoggingOnAPrayer]

Alyssa > Megan Makin Money

[@lukebowden5264]

These are my barstool Chicago guys

[@Belushibrotherfan64]

Hope you guys do this for all seasons

[@jonroelofs3102]

These are the best shows on RUclips. Everybody from barstool Chicago does a great job. Please don’t stop being the awesome people that you are. Jon from Ann Arbor

[@DukeICT]

Who would’ve thought Eddy had the rizz
Way to go buddy

[@mikeb1938]

Eddie the goat

[@CollinFromCincy]

Chief is looking good these days

[@KellyDM]

Yup! 100%.

[@drewmania6034]

Definitely would

[@jamesd3412]

Im just glad WSD got his oysters 😂

[@lukebowden5264]

I love her

[@jamescameron204]

9:42 wsd getting that bonus earmarked for the hair transplant yet?

[@pm3550]

Why is there no setup or did i miss something?

[@WalkerA92]

Dave is definitely the guy to care more about showing off than pursuing a girl. Terrible first date idea

[@Portez77]

"The angry type"? GIRL what kinda men you dating?? 😂

[@cpm4778]

16:46 Break her wrist tough guy

[@youngtender8737]

Alyssa is a smoke show

[@tropx8995]

Is that how you go out on a date? Everybody wearing hoodies?

[@DJMILKMAN321]

BLVD fucking BLOWS man.

[@southernjw]

Poor Eddy, will he ever have the confidence to date.

[@googlekrishna7025]

🫡🫡🫡

[@mattthompson4005]

Eddie is an excuse guy

[@MayorMcCheese2000]

meh

[@gunit8315]

I like blondes

[@gregp1406]

Good thing alyssa isn’t a blonde