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Cold Weather Date Ideas In Chicago

frozen heart

Fellas…let’s paint a little picture here. You met a nice girl at the 9th Ugly Christmas sweater party you went to in December. You’ve been texting a little bit, but it was the holidays so you didn’t get to get together again until mid-January. You agreed to go out for drinks, it went great! So great that you asked her if she was hungry after your third round and decided to extend the drinks to dinner and you know a great little thai place near by. The night ends and you give her a soft kiss as she gets into the uber you called for her because wow are you a gentlemen. You’re trying to make plans for a fun second date, but then Cheryl Scott hits you with some bad news.

This week rolls along and you send her a text.

You: Hey any plans this weekend?

Her: Nothing yet (winky face emoji)

you’re feeling yourself after that winky face. 

You: It’s so cold and miserable. I don’t want to leave the house!

Her: OMG I knowwwww

You: You wanna come over order some food and watch that new Ted Bundy series on Netflix?



5 minutes goes by and you panic. The text bubble dots are gone. Netflix and chill with the Handsome murder guy documentary as a second date?!?! What were you thinking?  You could’ve said anything. Maybe like 


Oh shit….this might work…



You: You want to grab dinner somewhere and go do something?

Her: Sure! What’d you have in mind?

Phew…you’re in. Now you have to have something in mind because what you mean by “do something”

is not the same “do something” she was thinking. How do I know she’s not thinking that? Pick up your phone, open the camera, and hit the reverse angle. That’s YOUR face. Good fucking luck. You need to be funny. You need to be charming. You need to feed her and also mix in some alcohols to help make you funny.

Step 1) Picking A Restaurant

She’s “not in the mood for anything so you pick”, but you have to pick something she’s in the mood for so good luck. Realistically, they’re all going to be the same. Find a place where you’re going to spend like $80 on an appetizer, entres, and cocktails. Make it Mexican. Who cares? Nobody remembers the second date restaurant.

Step 2) Pick An Activity 

Obviously has to be indoors. It’s too miserable for anything else. You want to limit the amount of time outside so pick a venue you can be in for over an hour. Here are a few ideas in no particular order.

Chicago Art Institute

art institute

You’re a cultured and intelligent young man. Well you’re not, but you’d like people to think you are. So you suggest the Art Institute. Walking around. Subject matter right there for you to talk about in case your conversation stalls. She will also pretend to like the Art Institute. Here is how it’ll go

AI 1

“Hmm, this is interesting. People in the rain(one-mississippi, two-mississippi, three-mississippi…walk to another one)”

Ai 3

“oh wow, some old shit(one-mississippi, two-mississippi, three-misssissippi) hey I brought a flask, do you want a sip?”

This applies to really all of the museums. Walking around, being a little bit bored, pretending to be interested, making a few jokes. The experience is largely the same. Make sure you can get a little buzz on.

Go See A Movie

Dinner and a movie. Cliche much? Doesn’t matter. It’s an event. You have a ticket and every theatre has a bar this day so you can kill to birds with one stone. Get a little bit loaded and head on in. You chose “The Favourite”. You saw some Oscar buzz on twitter, but didn’t really know what it’s about. It’s weird. Very weird. Emma Stone gets a naked for second though. You can talk about that. Is she attractive? Hard to say sometimes.

Dive Bar With Games

Darts, shuffle board, pool, all that stuff. Make it fun. A little competitive. Playfully talk shit. She will probably push you away in a flirty way. You’re off to the races.

And finally…that’s it. That’s really all I got and I don’t even know if those ideas are good. All I know is that they’re inside. Girls…if you’re reading this and a guy asks you to hang out…just do the netflix and chill. Skip the weather and the bullshit. It’ll be fine.