Chicago – Drink Spots for your Dating Pleasure

Themesong of the Day:   (And if you like house music this is a badass track that you really need to listen to before you read the rest of this shit.)

I’m a doin research on the city now that my bartender jobs are kicking off.  One, because I like to explore.  Two, to make connections.  Three because I have 2 non-sexual fetishes; grocery stores and cool lounges and bars.  Four, My day-2s are not fancy despite community advice.  I just like to go have a drink or two then head to my place.

So I have been doing research both in person and online to find some cool drinks spots.  I’m gonna share them and maybe add more over time.   I probably wont post the shit you know.  I mean ya the local dive is cool and some chicks like that just as much as going to the 17 dollar a cocktail spot (which is not necessarily what I’m posting here – actually it’s Rebar in Trump that has $17 cocktials fyi).

We all know Big Star Taco, Violet Hour,  Inn Joy and all the nightclubs where we can get free drinks with the secret password so I just wanna put on here some shit I dug up or happened across on accident or with a little work involved.

So here we go.  No order or rhyme to my order or whatever.

Pegasus Restaurant and Taverna – Greek Food,  Greek Town and I may know the bartender here  serving up drinks here this summer on the “Roof Garden” as they call it, but I’m not saying who he is.  Laid back, nothing fancy, except for if said bartender make you a drink with Metaxa or Saint Germain, then things will Definitely get Fancy, and fucking Delicious!

Terrace at the Conrad – Check this out.  #1 – I’m a big fan of Terrace bars.  I think subconsciously it may be one reason I moved to the city.  So these guys have one.  Even fucking better is Imagine telling a chick, “Let’s go see a movie tonight.” and after she’s thinking “How fucking lame…” you take her here for Sunday free moving night.  This is on my Must Do list.

The Drawing Room – You probably passed this place a hundred times if you are walking near the Viagra Triangle.  It’s a hidden little underground lounge ala Mixology.  Cool little tables and comfortable seating, and they do full on mixology, but not in a really stuffy way.  I always HEAR it gets busy, but I never have SEEN it busy.  So that’s GREAT for a Day-2.  It’s not dead ever either so it wont be a ghost town.  The atmosphere is pretty chic and ultra-loungy.  Totally fits the “Underground Lounge” vibe if you’ve ever been to any in other big cities.

Delilah’s – If she’s into dive bars, she’s a hipster, a rocker chick, a wannabe suicide girl (or a real one) or she just likes whiskey a lot this is your spot.  They have shitloads of whiskey; apparently the largest selection in Chicago.  They have rockabilly nights, a kind of dark and broody atmosphere that, honestly, I kinda like from time to time and pool tables so you can play grab ass.

Cal’s Bar – Divey with a dash of hipster and some live music in the midst of the city.  It’s a Liquor Store, and an Attached bar.  Drinks are cheap and so is the atmosphere but I totally dig on the fact that they took it from some shady liquor store and made it into a shady bar/liquorstore with live music and despite the challenges are still going.  Watch the Video on their home page.  Cool shit.

The Trump –  Some of you hate Donald Trump.  I actually like the guy.  But regardless of that, maybe you’re Mr Moneybags OR Better yet, maybe your girl is Mz. Moneybags and she want’s to go somewhere fancy on her tab.  Well fuckin A.  You got choices here.  The Terrace and Rebar.  Expensive drinks, shmancy atmosphere and great city views.  And it’s Trump so you can either make fun of it or…  Well make fun of it.

The Peninsula Terrace – Totally Miami in my opinion.  This is the kind of place, at least by the pictures, that would be a cool place to chill and get your chick drunk before you go an bang the shit out of her.  Like I said, though, I just like terraces.  And those comfy couches and awning thingies.

Nomi – Some of these Hotel Bars are pretty fucking cool.  This one is located in the Park Hyatt Chicago.  I just like the atmosphere really.  It just seems that no one seems to be able to take a good picture of the joint so you’ll just have to trust me.  If not, you got shitty, beer smelling Pippins right across the street where you can feel your feet sticking to the floor.’s+NoMI+Floor

Emerald Loop – It’s late, you’re downtown and you don’t wanna go to Hubbard or Rush and Division and you want a good cheap drink at an Irish bar that’s not hammered by drunk college kids, but wont be dead, so you can run your Patented “I’m going to fuck you in the ass later” pattern on here uninterrupted.  Maybe I just like this place because after ordering 5 or so drinks the tab always seems to be around $10; but I’m industry and they like me so go figure.  It’s still a cool Irish bar by any standard.

Maude’s Liquor Bar – I have this weird fetish (apparently it’s my thrid non-sexual fetish) with the West Loop.  I think it’s because it’s got that old warehouse district vibe.  What I don’t get excited about are the places like Market or Haymarket that everyone raves about.  Not that they’re bad places, they just don’t excite me.  Maude’s is full on Hipster Mixology, and I didn’t hate it.  Get ready to hear a fucking monologue about your drink from the bartender if he’s the guy I had.  The drinks are ok, and the atmosphere is kinda like an old, french speakeasy.  Simple but Not simple at all.

The Gingerman – Wrigleyville’s original Non-Wrigleyville bar.  This is more of a step above a dive bar.  Good beer selection, cheap, the atmosphere is clean, but it attracts a sort of rockeresque crowd with a dash of hipster but not overpowering.  If I remember correctly they have free pool.  Also there’s lots of room for you to take your chick and sit somewhere and chat her up.  I just like this place.  Oh, and it has a Jukebox with good fucking songs.

Trader Todd’s – A Key West Bar in Wrigleyville.  What the fuck right?  But I have pulled a few chicks back to my place after meeting them here.  I kinda like Key West Bars because, well, I lived in Key West.  Also, they have Karaoke here like every night but they have some fat dipshit Karaoke guy who has pissed me off twice when I was here, the second time I told him, “Why don’t you just mind your own business and do your fucking Karaoke.”  But despite that I like the place.  They have OJ they will squeeze fresh for your drinks and a good beer selection.  And a boat inside.  AND they have a bus that on Friday’s and Saturdays will pick you up almost anywhere in the city and take you to their bar for free.  I’m assuming you are expected to buy a drink or two on the ride over so if you’re gonna pull the ever popular PUA “I’m drinking water tonight.” then I don’t know If I’d consider the party bus option.

Matilda – So this is pretty cool.  Located a little north of Belmont on Sheffield, it has kind of a funky atmosphere that is dark and I can’t seem to describe it.  Not dark and broody, really.  More like someone’s art project.  You have to see if for yourself.  Also they have Wifi.  And they have a good beer selection and $5 wine by the glass wednesdays for you cheapasses… Like me.  And Hyatt Merlot is Delicious!  On Weekends the Downstairs bar, Baby-Atlas, opens up and the place seems to get a little crowded.

For now I’m pretty done with my list.  I have a few more floating around in my head AND I am no where NEAR done exploring the bars and hidden gems of this city.  But this should keep you busy for a bit.  I will update this thread later.

If you have some cool places you’ve been to that I haven’t mentioned and you think some of us might not know about, do fucking share.



Ya I know, I haven’t updated in a while and not so regularly.  I can’t even promise I will start.  Let’s just say life is ups and downs.  I got a job I thought would be cool, at Tavern at the Park here in Chicago and then realized quickly enough that one of the Owners was a drunk who was trying to hide it by basically trying to power trip on his employees.  That shit rolled down hill and got old very fast.  So I looked for another job and I am just now starting that one.  I have no idea how things will be here, and how people and management will act, yet.  Regardless I can tell it’s already laid back way more than Tavern was, and not so dumb.

By the way, did you know you can actually rate your employers now, like Yelp?  I think this is totally cool and needed so check it out.  The site is called Glassdoor.  (and while you’re there you can read the employee reviews on Tavern at the Park)  😉

That’s all for now….


6 responses to “Chicago – Drink Spots for your Dating Pleasure

  1. All these places sound like cool places for a date, depending on one’s mood. Of course, what really matters is the quality of the company. I could go to a “lame” movie as you called it and enjoy myself just fine if I like the company.

    and by the way, in general I wouldn’t recommend drunk sex. Drunk sex is usually bad sex, you’re just too drunk to realize it. buzzed sex, okay – sober sex good too.

    • Thanks for your thoughts. Ya, the key to having a drink with a girl is not to get wasted. When you go out for drinks it’s to have a drink or two or three, having to bounce from one spot to the next to keep things interesting. I like going to about two or three different spots and then if things are going well the final spot is my place or her place. I almost NEVER have more that 1 drink at any of these spots. I’m creating memories for her to look back at. When you bounce locations she can look back at more stuff you did together and it creates a sense that you’ve known each other longer. Plus, like I said, it just keeps things interesting.

      • Hmmmm….I think I’m more of a go to one place and hang out and chill type of person. For me hanging out and talking and having a good time gives me a sense of knowing the person. Whether I want to have sex with them or not depends on lots of things – but I know you love to be the player, but I’ve got to tell you, nothing turns me off quicker then when I smell a player in my midst. I say he can go find other women to fuck, I’m not interested. I’m looking for a genuine connection, genuine and mutual appreciation for each other’s company, and yes, raw animal attraction too. Too me a player is looking to get his ego and his dick stroked.

        that’s all great for him, but what’s in it for the woman? to me, nothing. I think women who go for players are insecure and need their own ego’s stroked.

        Doesn’t sound very satisfying to me. If I don’t feel a sense of a real potential to fall in love, I don’t see the point. I feel no desire to get naked with a man otherwise. Sure, maybe it will only last a few months and then you realize it’s going no where – but that spark has to be there for me. Players don’t emit that kind of spark.

        • Ahhhhh… I love it when girls try to describe me. . . You should go back and read more of my blog posts. I AM a player, but a new breed of player… I actually genuinely care for and appreciate the women in my life. I didn’t become a player to fuck over women, I became a player to survive in a hostile environment of modern dating. 🙂 I love connection. I Love quality time with women. I love getting to know but what I love even better is that all embracing place of the knowing. If I had my choice we could all slip past the “getting to know” part right to the knowing. . . Seduction and being a player are two totally different things, love. . . My job is to bring pleasure to the women of the world and thus bring myself pleasure. . . Maybe I’m selfish but I’m damn good at what I do. Oh and by the bye. I tend to be selective about which women I share my gifts with. . . . 🙂

          • and love? what about love for you? and please don’t say you love all the women you connect with.

            But see, you are making my point. How intimate can one really be with a woman if you move on to the next one to “connect” yet again. That doesn’t sound like true connection to me. Awesome that you’re such a great lover, but from what I hear from you, I still wouldn’t want to sleep with you.

            I want to sleep with a man who loves me – I’ve never heard you talk about women and love in a way that I found compelling. I’ve only heard you talk about women and sex in a way that suggests you know your way around a woman’s body. Good for you. I suspect your lovers are very satisfied. And yes maybe the enjoy your company.

            and frankly, I find your self confidence a bit of a turn off. It’s too much. If I was chatting with you in a bar, I’d eventually walk away.

            I think you, my dear, could not seduce me. At least not with anything I’ve heard here.

            And yes, I know my way around a man’s body – and I only want to share that with someone who is very special to me.

          • Why can’t I say that if it’s true?

            And something else, I think it’s cute that you’re leaving comments on my blog telling me I couldn’t have sex with you and couldn’t seduce you and you wouldn’t like my confidence.

            Sounds to me you’ve been doing a bit of thinking about what I could and could not do to you… 😉

            It’s like the women that come over my house to hang out and say, “Nothing’s going to happen,” or even in once case where a women said ever so blatantly to me, “We are NOT fucking tonight.”

            There’s a certain point in one’s life where you learn that women change their mind pretty quickly about these things.

            PS – I think you LOVE my confidence. You’re just not used to modern men having any. 😉


Leave a Comment

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s