What to Talk About on a Date If You Already Know the Person

What to Talk About on a Date If You Already Know the Person

No matter how far back you go with someone, it can be intimidating to think about what to talk about on a date if you already know the person. Because you have at least a basic knowledge of each other, certain first date questions won’t make sense on this sort of date.

Regardless of how you know the person, it’s important to keep in mind that some standard first date rules will still apply:

  • Make sure you pick her up, pull the chair out for her, pay, and show other forms of chivalry
  • Show initiative and intent by securing a time, date, and location (what we refer to as TDL) for this date, as well as the second and third date

Without further adieu, take a look below for my professional tips on what to talk about on a date if you already know the person, whether it’s a coworker a friend or even an ex.

And because everyone’s situation is unique, I am including some information at the end of the article on how you can connect with me to have the most success on your date.

When It’s Your First Date With a Coworker

What to Talk About on a Date If You Already Know the Person

First things first — DON’T get bogged down in work talk and venting about work. Take this opportunity to get to know your colleague’s interests and personality outside of the confines of the office. Some important things to keep in mind in this particular situation are:

Keeping it Light

Maybe you and your coworker have been attracted to each other for a long time, but you were worried about crossing a boundary. Wanting to get to know someone romantically who is off limits can stoke the sexual tension and leave you feeling exhilarated when you FINALLY get to go on a first date with them.

That being said, remember that you actually don’t really know this person outside of work, and the fact that they were forbidden fruit could have actually made you idealize what they’d be like as a girlfriend. And she might have idealized you in the same way.

As exciting as the first date might be for both of you, remember that the reason for you not initially going out is something rather common — work. It’s not like your families are the Capulets and the Montagues.

Maybe you two will end up together forever, or maybe you’ll discover that you’re not as compatible as you once thought.

Regardless, it’s in your best interest to keep the conversation light. Ask about her interests outside of work, what she was like growing up, etc.

So what do you do when you’re not a superstar lawyer?

What’s an average Sunday look like for the magnificent Maggie?

If you weren’t a lawyer what would you be?

Using What You Already Know

One of the advantages of going on a date with someone you already know is that you’re coming into the situation equipped with information you wouldn’t have otherwise. If you’ve chatted about shared musical interests, for example, you can talk about plans to see one of your favorite bands or a concert that you think she would like.

What To Talk About When She’s A Friend Of A Friend

If you’re on a date with a friend of a friend, first of all you should be profusely thanking the friend that set you up.

Not only because they set you up with a cutey, but because they will now be the basis of your conversation.

I’m not saying you need to talk about Steve for the entire first date – she might get the wrong idea. But use Steve as a starting point.

Ask her how she knows Steve, chat about your relationships with him, and naturally grow the conversation from there.

Some questions you might ask are:

Hey have you ever noticed that Steve is always using the word, defenestration – what’s up with that?

Steve’s a great guy, how did you meet him?

These aren’t ground-breaking super probing questions – but they don’t have to be. You’re allowed to keep things light initially as you begin the conversation by revolving it around the one thing that you know binds the two of you – good ol’ Steve.

Scoring a date through a friend of a friend is one of the best and easiest ways to meet women. In our program, Dating Decoded we’ll show you how to mine your existing social channels for dates. We’ll teach you the art of asking your friends to set you up. There are endless benefits to being set up by a friend including:

  • You have a date without having to do work
  • She won’t think you’re a creep because you’ve been pre-screened
  • You’ll probably like her because your friend knows you and is (hopefully) a good judge of character
  • She’s probably already into you because your friend talked you up
  • You two already have a few things in common (as evidenced by being friends withe same person)

It’s easier to bond with a friend of a friend. You two have a mutual friend for a reason. Chances are you’re similar enough to really hit it off.

Other Passions

One thing that can create attraction between coworkers is a shared passion for your chosen vocation. Although it’s best to steer clear of conversation that relates to where you both work, there’s nothing wrong with learning more about her career passions outside of her current job.

You can also use the opportunity to find out what led her to the company you both work at now, as well as where she pictures herself working if she doesn’t intend to stay at the job for a long time.

Dating a coworker can be tricky business. If you’re finding yourself interested in someone you work with, click here to learn more about the rules that come with dating a colleague.

What does the perfect day look like for you?

If you were to play hooky from work what would you do, where would you go?

When It’s Your First Date With a Friend

What to Talk About on a Date If You Already Know the Person

Welcome to the first step out of the friend zone! Woohoo!

When you’re going on a first date with someone you already know, and that someone happens to be a friend (not an ex, not a co-worker, not an acquaintance, but a friend) you’re already set up for success.

Good friendships come with a foundation of compassion, trust, and respect. Those three elements are also integral to a successful romantic relationship.

Because you two already have a great time hanging out as friends, it shouldn’t be difficult getting the conversation to flow. If your friend has agreed to go on a date with you (or even been the one to ask you out), it’s because she’s already hip to the fact that you are one awesome guy. For that reason, it’s really important that you be yourself during the date and act as normal as possible.

Still, women love mystery, so don’t go on the date without showing you have a few tricks up your sleeve. Reveal something about yourself that she doesn’t know already know. Show her your more sensitive, romantic side and don’t shy away from turning up the heat.

Break the touch barrier between you two but resting your hand on a non-threatening area (a shoulder, knee or her forearm) during the conversation. Do all the things you would normally do to show your chivalry during a date, such as picking her up, paying and walking her to her door. If things go well and the chemistry you anticipated is there, chances are good that this lucky lady could go from being your friend to your girlfriend.

Be honest, did you ever think we’d go on a date?

When did you first feel attracted to me?

We know each other pretty well, but tell me something I don’t already know about you.

When It’s Your First Date After A Break

What to Talk About on a Date If You Already Know the Person

Obviously, you’re going to be extremely excited to date your former partner after a break. It feels like the very first time you two have gone out as you’re both recharged and are looking at this relationship through a new lens.

Chances are if you’re now done with your break and dating again, you two have already had in-depth conversations about how you feel about each other, the future, why the break too place, etc.

There is no reason to re-hash these things – especially when you’re on a date!

To make sure things go smoothly, I recommend revolving the date around an activity.

Things have the potential to get a little awkward so why not put the spotlight on the activity rather than on yourselves?

That activity could be as simple as going on a hike or bike ride.

Considering this is your second-chance at a relationship you clearly care about I recommend doing something special or at least out of the norm. Think of something your partner is super into and build a date around that. Show her how much she means to you by crafting a super special date.

If she loves tarot cards, go for a reading. Maybe she’s a massive sports fan, so go watch her favorite team live. And if she loves dancing to live music go see a show.

Whatever you do try not to go to just another boring dinner or worse – get coffee.

Plan the date around an activity and you won’t have to worry about what to talk about as the conversation will flow naturally.

The 70-30 Rule

If you want someone to like you, allow them to do most of the talking. This is Dale Carnegie’s advice, the author of the second most popular book behind the Bible, How To Win Friends And Influence People.

Everyone’s favorite subject is themselves, so let them do the talking. Not only this, but we absolutely love when we feel as though someone else genuinely cares about what we have to share and who we are.

By asking probing questions and genuinely caring about the answers (as shown by nonverbal cues and by asking follow-up questions) you can quickly build attraction.

Listen to what she has to say, care, and ask follow-up questions. Doing this may not guarantee a second date but it will certainly endear you to her.

I should also note that questions should arise organically. Randomly asking her a question out of the blue could throw a wrench in an already flowing conversation. Keep things natural, smooth, and free-flowing.

Refine Your In-Person Dating Skills

When it comes to going on a first date with someone you already know, everyone’s situation is unique.

In our coaching program, Dating Decoded we offer modules via our online curriculum that dive deep into how to have amazing first date conversations. We also tackle this subject via our two weekly live coaching sessions. But even though equip you with the skills you need to have amazing first dates you still need a safe place to practice.

That’s where our mock dates come into play.

Practice what you’ve learned in our program withe Audrey or Brooke, our mock date specialists. In-person or online you’ll have a practice date to use and refine the skills learned in our program. After the date you’ll received detailed feedback on what worked and what areas need improvement.

To learn more about our program and how we can help you prepare for your big first date, book a 1-on-1 Zoom call. 

Here we’ll talk about your dating history and dating goals.

And if you’d like to know how our students’ lives have changed after enrolling in Dating Decoded, hear what they have to say here. Or, just check out one of our student’s video reviews here:



50 of The Best Date Ideas Chicago Has to Offer

best date ideas chicago

Looking for some of the best date ideas Chicago has to offer?

Chicago is a single man’s playground. The Windy City is the nation’s third largest city, boasts a ratio of 116 unmarried women per 100 unmarried men, and has the second highest number of bars and restaurants per capita among the 50 largest metro areas in the US.

Living in a playground is one thing, knowing how to efficiently get the most out of the toys is another.

If you’re a proponent of MegaDating you know that the initial dating period is the most delicate. To date efficiently, the MegaDating philosophy urges followers to adhere to the following guidelines for the first three dates. This article will categorize dates depending on their juncture.

First Date

First dates should be kept to a one-hour maximum with no more than $20 being spent. This ensures that you’ll have more time and money to spend on other dates should this one not work out.

Second Date

Second dates are active and 100% free. Active dates increase heart rate, help you bond over a shared activity and are great for breaking the touch barrier. They should be free to scare away gold diggers.

Third Date

If she’s lucky enough to make it to a third date show her how special she is by spending big, getting fancy, and making it a night to remember.

The following recommendations come to us from dating coaches, professionals, locals, and from yours truly -a former Chicago resident. Without further foreplay, let’s reveal the top 50 best date ideas in Chicago.

First Date Ideas Chicago

First Date Ideas Chicago #1: The Wormhole Coffee (Wicker Park)

wormhole coffee

wormhole coffee shopThe Wormhole Coffee is located in the Wicker Park neighborhood. You’ll notice a giant DeLorean on the wall from Back to Future and many other 80s movie themed props. Choose from a variety of creative lattes and specialty drinks with café style seating.”

-Recommendation by Lo Najar, Business Coach and Sales Strategist at Lo Najar Coaching

I’ll admit it. Cafe joints can be awkward for first dates. With everyone either reading or pretending to write a novel, a cliche first date question can tear through the silence. Lucky for you, The Wormhole has a few nooks that grant daters the privacy they need for a first date to thrive.

First Date Ideas Chicago #2: Grab a Drink & Walk Around Randolph Street Market (West Loop)

first date ideas chicago

randolph market chicagoThis market is one of the best in the city because you can sip a mimosa, listen to live music, and browse tons of arts and antiques. Plus, it’s the last weekend of every month. It’s great for people watching and there’s something for everyone (crafts, antiques, weird jewelry, records, books, etc.).

-Recommendation by Sarah Ashley, Chicago Local and Freelance Copywriter

Arguably Chicago’s most eclectic market, Randolph Street Market is a must for a first date. For just two days every month, 100+ vendors flock to Chicago’s most prized market to sell their goods. It’s lively, effervescent with craft beer, and is the ideal spot for a first date. If the crowds prove to be too much, take a brief walk over to the adjacent Union Park.

First Date Ideas Chicago #3: Sawada Coffee (West Loop)

first date ideas chicago

sawada coffee-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Both affordable and hipster-friendly, Sawada Coffee is owned by world-renowned barista and 2008 Free Pour Latte Art world champion, Sawada Hiroshi. This industrial warehouse-turned cafe will give you and your date plenty of privacy to toss some awkward first-date questions back and forth.

#4: Loba Pastry & Coffee (Roscoe Village)

date ideas chicago

loba pastry-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Nothing quite pairs as well as a pastry and cup of coffee. Loba makes for a relaxing first date location, just be aware of their limited hours. If your schedule allows for it, this would be a great spot for a mid-day mid-week first date.

#5: Broken English Taco Pub (The Loop, Old Town, Lincoln Park)

unique date ideas chicago

Broken English ChicagoBroken English Taco Pub is perfect for happy hour OR Taco Tuesday!  Can’t go wrong with $2 tacos and a bunch of other drink specials. A big Lucha Libre theme and many Instagram opportunities with gorgeous décor.”

-Recommendation by Lo Najar, Business Coach and Sales Strategist at Lo Najar Coaching

We don’t normally recommend restaurants for first dates, but we’ll make an exception for restaurants that have killer happy hours. Remember that first dates should be kept under $10. But with some of the best happy hours deals in town (M-Th $3 house beer, $2 Taco Tuesday, etc.) the Broken English Taco Pub is a safe choice. Not only does it fulfill MegaDating guidelines, but with three locations sprinkled across Chicago, it’ll never be an out-of-the-way date spot.

#6: Bring Your Date to Windy Kitty Cat Cafe (Wicker Park)

cat date ideas chicago

windy kitty chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

It’s a freakin’ cat cafe, need I say more? The only people that should avoid such a spot are devout dog lovers and people with allergies. Lame people aside, everyone that’s ever been here has loved it.

This is an amazing date idea because you’ll get a chance to play with their 30 or so cats and kittens – that are from the shelter. It’s also advised that you make a reservation before bringing your date to this epic kitty club. Lastly, just make sure to not bring in your cats as it’s currently not allowed. There are plenty of cats you can play with that need some love. 

Note from Windy Kitty: “A lot of guys surprise their significant others with this as a date and kitten corner is such a great spot! Bringing someone here is definitely a way to win somebody’s heart.”

First Date Ideas Chicago #7: Big Shoulders Coffee (The Loop, West Town, Gold Coast,  CBOT, River North, Midway Airport) 

big shoulders coffee date

date ideas chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Fresh roasted artisanal coffee anyone? Big Shoulders operates out of 6 six different establishments throughout the city. Each cafe has its own unique hours and lack of aesthetic, but for what it lacks in beauty it makes up in quality. This spot is known to both locals and transplants as one of the best coffee joints in Chicago.

#8: Doughnut Vault (River North)

doughnut vault

best date ideas chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

You’re jittery, doubts are rushing through your head, and you suddenly have a craving for something sweet and diabetes-inducing. First dates are awkward and stressful by nature. Mitigate those nerves by indulging in a cheat day when you bite into one of the Doughnut Vault’s finest.

First Date Ideas Chicago #9: Firecakes Donuts (River North, Lincoln Park, Oak Park, Loop – Wells St. Market, Billy The Truck)

firecakes donuts date idea

firecakes chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Firecakes is a company that’s been in the making since the 1930s when the owner’s great grandfather used to bake backwater donuts called, “firecakes” for loggers in Wisconsin. Taking her to a place she’s surely never been to, to try a bastard donut is a perfect first date idea.

#10: Molly’s Cupcakes (Lincoln Park, Magnificent Mile)

mollys chicago

best date ideas chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

What if I told you that you could support local schools, eat at a place that’s been featured in the Chicago Tribune, and eat a fresh cupcake while on a swing all at the same time? You’ll be so busy enjoying yourself that you’ll completely forget about those first date nerves.

#11: Original Rainbow Cone

original rainbow cone chicagooriginal rainbow cone chicago date idea-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Grandpa Joe created the rainbow cone in 1926. Unsatisfied with the lack of ice cream flavors, Joe and his wife decided to make a host of new flavors. Stack them all together and you get the rainbow cone. Located in Beverly, The Original Rainbow Cone is a great date spot for those seeking to enjoy one of Chicago’s oldest and proudest establishments.

First Date Ideas Chicago #12: Margie’s Candies (Bucktown, Ravenswood)

margies candies chicagobest date ideas chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

There are few eateries more legendary than Margie’s Candies. Famous actors, ball players, and even Al Capone himself have all stuffed their faces with Margie’s epic ice cream sundae.

#13: Jeni’s Splendid Ice Creams (Southport, Wicker Park, North Wells, Armitage, West Loop, Wrigleyville, Oakbrook Center)

jenis icecream chicagoicecream date idea chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Lines out of the door is a solid indication that maybe you should open another ice cream joint. Lines out of both doors indicate the same. Eventually, Jeni’s had so many lines out of so many doors that they decided to open 7 ice cream parlors.

#14: Sprinkles Chicago (Streeterville)

first date idea chicagocupcake date idea chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Perhaps Sprinkles might not have the same history as other sweet-tooth eateries, it does have convenience. First dates should typically happen midweek just after work. Sprinkles is open M-S, 9-9.

First Date Ideas Chicago #15: Katherine Anne Confections (Palmer Square)

date idea chicagokatherine anne confections chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Locally made, locally consumed. Katherine Anne Confections is the go-to spot for hand-dipped truffles, soft honey caramels, and gourmet marshmallows. Katherine Anne is the last first date spot on our list but it’s certainly worth checking out, especially if you’re already in the Palmer Square barrio.

Second Date Ideas Chicago

Second Date Ideas Chicago #16: Bike Lake Shore Drive

lake front trail date idea

lake front trailLake Shore Drive is an 18 mile paved bike path accessible at any point in the city. Witness gorgeous views throughout diverse neighborhoods and of course; you are riding along Lake Michigan the entire time.”

-Recommendation by Lo Najar, Business Coach and Sales Strategist at Lo Najar Coaching

Remember, second dates are meant to be both active and free. Tell your date to bring her bike so that the two of you can build the foundation of your relationship on being adventurous and healthy.

#17: Walk Around Millennium Park (New East Side)

millenium park chicago

millennium park chicagoYeah baby! Located between Michigan and Columbus Avenues in Randolph Street, this is like a separate town square right in the middle of the city. Exhibitions, shows, concerts all form part of these vibrant attractions to locals and tourists. Go sit on the benches and take in the spectacular view, and obviously each other’s view. There are so many things to do here. Best of all….wait, wait… Entrance is free! You do however have to pay for food and drinks at least!”

-Recommendation by April Davis, President and Matchmaker of LUMASearch

Regardless of sun, snow, or catastrophic hail storms, you can be sure that Millenium Park will be buzzing. The park is great for a picnic or for a lovely Sunday afternoon jaunt.

#18: Yoga in Millennium Park

yoga millennium park“Every summer weekend in Chicago, you can participate in free Saturday morning yoga in Millennium Park. Bring your mat, towel and water and participate right in Millennium park.  To the east, your view is Lake Michigan and your view on the west is gorgeous skyscrapers – can’t beat the views and a calm Saturday morning in a busy city.”

-Recommendation by Lo Najar, Business Coach and Sales Strategist at Lo Najar Coaching

The park is awash with free stuff to do. Yoga is part of the city’s Summer workout series. Every Tuesday and Thursday free yoga classes begin at 7:30 sharp.

#19: Lincoln Park Zoo (Lincoln Park)

lincoln park zoo

chicago zooWomen have a soft spot for animals. Some of us like to hunt them and provide for our loved ones, but for a woman, a baby cub or a toying monkey is so cute. Lincoln Park Zoo is ideal when you are on a tight budget because it is free. Please play along with that you actually do like all animals and make sure she knows it. Hunting can wait till later..”

-Recommendation by April Davis, President and Matchmaker of LUMASearch

Zoos aren’t for everyone. While some people freak out when they see prairie dogs, others get depressed when they think about how underfed they must be. Know what your date thinks about the zoo before you surprise her with a trip to check out some of the most malnourished animals in all of Chicago.

Second Date Ideas Chicago #20: Take a Circus Class at Aloft Loft (Logan Square)

a loft loft circus class

a loft loft-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

An aerial skills class in a 100+-year-old church might just be the oddest second date you’ll ever have (right next to turtle racing). At least if you fall from the ceiling and die you won’t have to travel too far to get to heaven.

Chicago Date Ideas 2nd Date: #21: Invite Her to Your Co-Ed Softball Game

chicago social date idea

chicago social for a dateThere is a lot of sports clubs that you can join in Chicago. After the Polar Vortex, why not reinvigorate your limbs by running around with people who also like to run around. There is something about playing softball by the lakefront that allows one to escape feeling as though they are in the 3rd largest city in the United States. After a win or a loss, you can always grab a drink afterward with your teammates. Use the game as a way to bond with your date.”

-Recommendation by April Davis, President and Matchmaker of LUMASearch

You just learned that your left-fielder is going out of town and need a stand-in. Have you ever dated your left-fielder before? It’s kind of awesome. Have your date replace your teammate for a game or two as you two bond over how kickass you are as a team. Winning together is, well, winning. Go get physical.

#22: Get Active at Brooklyn Boulders (Greektown)

brooklyn boulders

brooklyn boulders-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Seriously though if you haven’t seen Free Solo by now you’re out of the loop. Live out your own free soloing adventure as you scale the walls at Brooklyn Boulders.

Second Date Ideas Chicago #23: Walk, Jog, or Bike the 606 Trail (Logan Square)

The 606 chicago

the 606 date idea-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Inspired by NY’s Highline, the 606 trail is a great place to chat while taking a scenic, leisurely stroll through Chicago.

#24: Get to Know Your Date at One of Chicago’s Free Beaches (Gold Coast, Lincoln Park, South Loop, Uptown, South Shore, etc.)

chicago beaches

beaches of chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Chicago has a ton of beaches. Sure it’s a lake, but you wouldn’t know it when you’re sipping on a craft beer and taking in the view. Have a picnic, bring your dogs, play a little volleyball. Whatever activity you want to engage it, the beach is the perfect place for a second date.

#25: Check Out a Video Game Art Gallery Event (Wicker Park)

video game art gallery

video game art gallery-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Dude. If she’s into video games and doesn’t already know about this place, you’ve scored. What gamer doesn’t love an establishment whose sole purpose is to appreciate video games.

#26: Check Out The Museum of Science and Industry (Jackson Park)

museum of science and industry

museum of science and industry-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Maybe even after you hit the video game gallery you can head over to the Museum Of Science And Industry. This is such a great date idea because it gives you two a topic to talk about. Sometimes daters can feel like they’re flailing for a conversational topic to grab onto. This problem is solved when you let science drive the conversation.

#27: The Smart Museum of Art (Hyde Park)

smart museum of art

art date idea chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Sure it sounds a little pretentious, and you know what, it kind of is. The Smart Museum of Art is a donation-based fine arts museum.

Second Date Ideas Chicago #28: Bad Axe Throwing (Lincoln Park, Near West Side)

bad axe throwing chicago

axe throwing date idea-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

For some reason, axe throwing is becoming popular all over the US. We can probably thank Game Of Thrones for the rise of the craze that has finally hit Chicago. No worries if your lady is just a novice -it’d kind of be badass if she weren’t- you two can act like badasses together.

Third Date Ideas Chicago

Third Date Ideas Chicago #29: Turtle Racing at Big Joe’s (Andersonville)

turtle racing

chicago turtle racing-Recommendation by Scott W. Chicago Local

Jolanda might just be the most popular woman at Big Joe’s. Jolanda’s been around longer than most, rarely wins races, but almost always wins you a free drink. She’s been racing at Big Joe’s every Friday at 9 p.m. for years now. Sure she typically comes in last out of the five turtles in the ring, but at Big Joe’s losers win free drinks. Yeah, it’s weird, but I guarantee you no one has ever said that turtle racing was a bad third date idea.

Third Date Ideas Chicago #30: Lula Cafe (Logan Square)lula cafe

lula cafe date idea

“It can be difficult in other cities to find something enjoyable to eat, especially if you have very specific food choices, (like vegan, paleo, gluten-free). But in Chicago, you’re in luck – especially at Lula’s Cafe, which is geared towards organic/farm to table.”

-Recommendation by April Davis, President and Matchmaker of LUMASearch

A third date should take place at night, has zero financial and time restrictions, and hopefully culminates in sex. Lula provides quality organic and vegan options in a funky backdrop.

#31: Upstairs at Gwen (River North)

gwen hotel for a date

gwen date idea

gwen chicago“Located in the Gwen hotel is their rooftop restaurant. My favorite is being able to eat outside on their rooftop with views of the entire city complete with private cabanas, tv’s, and bonfire pits. Gorgeous views right downtown.”

-Recommendation by Lo Najar, Business Coach and Sales Strategist at Lo Najar Coaching

For an upscale dinner head to the rooftop of the Gwen Hotel. The food, rooftop view, and general opulence of this place will make you feel like you’re on vacation. Seem like a solid Chicago date idea, don’t you think?

#32: The Chicago Diner (Logan Square)

chicago diner date idea

the chicago diner

“Food is a great way to explore passion and sensuality.” 

-Recommendation by April Davis, President and Matchmaker of LUMASearch

Should your date be a vegetarian, this is the spot for you. As the door proudly indicates, this diner joint has been meat free since 1983.

Third Date Ideas Chicago #33: Parson’s Chicken and Fish (Lincoln Park, Palmer Square)

parsons chicago

parsons chicken and fish“The fried chicken at Parson’s is simply awesome.”

-Recommendation by April Davis, President and Matchmaker of LUMASearch

Anyone up for some fresh seafood? Parson’s has got you covered.

#34: Union Sushi + Barbecue Bar (River North)

union sushi + barbeque bar

union sushi chicago“The name is for sure unique, as is the whole atmosphere. Great place for sushi and ramen, but with an American twist. Cocktail menu is great and unique, and anything on the menu is delicious. I love Union Sushi + Barbeque Bar for dinner, and in the summer the windows open up in the restaurant. One of my favorite places for a laid back date night!”

-Recommendation by Lo Najar, Business Coach and Sales Strategist at Lo Najar Coaching

Few menus can cover this sort of ground and still be good. Union Sushi lives up to the hype. It might be the only sushi place to call a retrofitted warehouse, but that only adds to its fusion charm.

#35: Do a Themed Boat Cruise on Lake Michigan

the odyssey chicago

dinner cruises chicago“Take your partner on an evening dinner boat cruise on this magnificent lake. The skyline sparkles in the background while the sparks between the two of you are getting brighter as the evening progresses. Cruise companies offer many themed cruises. Odyssey offers Sunset, Full moon, and other themed cruises. Maybe you will enjoy the fireworks dinner cruise best, as that is your goal, fireworks later right.”

-Recommendation by April Davis, President and Matchmaker of LUMASearch

If you really want to wow your lady, take her on a mini cruise getaway. Sure it’ll only be for a few hours, but you’ll be offered some of the best views, service, and disparate experiences Chicago has to offer.

#36: Chicago Magic Lounge (Andersonville)

chicago magic lounge

chicago magic show“You enter through a laundromat! It’s a more unique night out than say, a movie, because it’s slightly interactive and an adventure. It’s a bonding activity for sure and a great story to tell. “

-Recommendation by Sarah Ashley, Chicago Local and Freelance Copywriter

It’s weird, I know. But the goal of your third date is to stand out, not play it safe. Woo her by hitting up Chicago’s premier magic venue.

#37: Navy Pier’s Centennial Wheel

centennial wheel

centennial wheel“The Ferris wheel at the navy pier is an obvious date spot in Chicago because you are in your own world while the lake view and skylights go by slowly. Oh what a romantic long kiss will occur here for all the right reasons.”

-Recommendation by April Davis, President and Matchmaker of LUMASearch

Sure it’s cheesy, but name me a woman that doesn’t want to live her own version of The Notebook?

#38: Movie Night at Millennium Park

chicago movie night date idea

movies at millennium park“You can bring a picnic and set up shop in beautiful Millennium Park to watch a movie. Hint: it’s less about the movie and more about a fun time to enjoy a flick, sip some wine, and enjoy Chicago while it’s actually warm outside.”

-Recommendation by Sarah Ashley, Chicago Local and Freelance Copywriter

Netflix and chill is one thing. Watching a movie in Millennium Park is another. Most everyone wants to watch a movie here though only few have. This year they’ll screen movies such as: Black Panther, Frida, Fences, The Wiz and more.

Third Date Ideas Chicago #39: Tango Sur (Lake View)

tango sur

tango sur“Dinner by candlelight. This restaurant located in Southport Avenue is ideal for a romantic date night for couples. The food is great and the romantic ambiance will have your dessert somewhere else. Remember it is BYOB (bring your own bottle).”

-Recommendation by April Davis, President and Matchmaker of LUMASearch

Meat on meat on meat. That’s what to expect when you mosey into an Argentine restaurant. This place has a killer combination of food and romance.

#40: Bistro Campagne (Ravenswood)

bistro campagne

chicago date ideas bistro campagne“If you’re looking for a standard romantic dinner, this is the place. Highly recommend sitting outside in the courtyard, which is full of twinkly lights and trees, so you really feel like you’re in Europe. Lincoln Square is super cute, too, so after dinner a nice stroll is always a fun dessert (unless of course you’re too full after the escargots, duck confit, and creme brulee!).”

-Recommendation by Sarah Ashley, Chicago Local and Freelance Copywriter

No time is more fitting for a fancy French restaurant than a third date. It’s got candles, cutsy lights, and opulent dessert options. You can’t really go wrong with a French restaurant as far as gastronomic foreplay goes.

#41: Go to a Second City Show (Old Town Triangle)

the second city chicago

the second city chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Canadian PM Justin Trudeau was sighted here just last May. If it’s good enough for the second most important man in Canada (Drake being #1) then I’m sure you and your date will approve.

#42: Checkout a Classic Film @ Music Box Theatre (Wrigleyville)

music box theatre chicago

music box theatre chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Are you two just not turned on by the lame Hollywood movies of today? The Music Box Theatre is one of the oldest theaters in Chicago. It exclusively plays movies – that like itself – stand the test of time.

#43: Adler After Dark Date Night (Northerly Island)

adler after dark date idea chicago

adler after dark date-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Does looking up at the stars in a planetarium get any more romantic? Sure you could be singing and floating around like Emma Stone and Ryan Gosling, but staying on the ground and gazing up into the never-ending expanse of space is still pretty magical. Galileo would agree.

Third Date Ideas Chicago #44: Wine and Paint Night at Bottle & Bottega

bottle and bottega chicago

bottle and bottega chiacago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

Tipsy painting, I think yes. Should you two strike up a lasting partnership after this date, painting and sipping on Malbec can become your new shared hobby.

#45: Grab a Beer or Tour at Malt Row (Ravenswood)

malt row chicago

malt row chicago-Recommendation by Emyli Lovz, Ex-Chicago Local, Cubs Fan, & Founder of emlovz

If the Netflix original show, Easy, based entirely in Chicago has taught us anything it’s that you’re bound to run across a beer snob while dating in Chicago. When this happens be sure to bring them to a quality brewery. Malt Row is that brewery.

#46: Go Dancing @ Beauty Bar (Noble Square)

the beauty bar chicago

the beauty bar chicagoIt seems as though in Chicago, everyone is a musician, or they are friends with someone who is a musician. Since there are so many of them, that means there is an abundance of different open mic and open jam nights throughout the city. Beauty Bar is a must, especially if you and your date like to dance.”

-Recommendation by April Davis, President and Matchmaker of LUMASearch

The Beauty Bar isn’t for timid dancers. People come here to shake their asses and get down. This place is a strictly third date destination. The dance spot likes to change the music up, so check to see what the DJ is spinning before you go, or don’t and roll with the tempo. Be warned that this place can get both packed and loud. Be sure that your dynamic can stand up against loud music and sweaty dudes.

#47: Cubs Game @ Wrigley Field (Wrigleyville)date ideas for couples chicago

wrigley field

-Recommendation by Chris and Cathy T, Chicago Locals

Come on now. Wrigley Field is the most outlandish, storied, cursed, ludicrous ballpark in America. It looks like what would happen if Frederick Olmsted designed a stadium.

#48: Logan Square Improv

logan square improv

For just $5 you can see a show every Wednesday-Sunday.

This is perhaps the most original date you two can go on. With shows being brief and cheap you should definitely pair this date spot with a nice dinner if you’re using it as third date idea. The venue is surrounded by dozens of amazing food options (and no I’m not referring to IHOP).

#49: Cook Class At Chopping Block

chopping block

Do you really want to make your new lady a dish but have zero culinary ability?

That’s fine – learn together when you two sign up for a cooking class. As I look at their calendar I see that they currently offer classes on how to make a tart, classic New Orleans dishes, pasta, and chicken fricassee.

The Chopping Block also offers virtual classes. Maybe you want to invite her over for a date night at your house where you two first take a virtual cooking class followed by eating good food and smooches for dessert.

Sounds pretty tasty to me.

#50: SPIN Chicago Ping Pong


Are you and your date the competitive type?

If so, why not put your money where your mouth is and back up those ping-pong skills as you two duke it out at SPIN.

Just book a table and enjoy.

SPIN also has monthly art competitions while DJs spin hip yet aggressive background music – trust me, it’s a vibe.


Now you know where to take your next date in the great city of Chicago. But what if you’ve been out of the dating game for some time? What if you’re a little uneasy about your dating skills? Have you thought about hiring a coach to help you? If so, I’d love to assist you.

Enrolling in our program, Dating Decoded means committing to a complete revamp of your dating skills and strategy, ultimately leading to more dates and a super compatible romantic partner.

Our program is exclusively open to men and is designed to give you the skills you need to succeed in the modern dating scene.

Our program is broken down into four pillars:

  • MegaDating – Dating various women at once to avoid settling and quickly find your ideal partner
  • The Perfect Profile – Online dating is the most popular way to meet your new partner, we’ll show you how to attract her attention
  • MegaMessaging – Learn how to chat with women online and ask them out using a TDL
  • Date Blueprint – Master the first three dates of any new relationship with our dating blueprint

If you’re interested in joining my program, feel free and book a new client session with me today. During this intro session we’ll assess your current dating issues and determine if my coaching program is a fit for you.

After three short months, you’ll be implementing MegaDating seamlessly, hacking dating applications, and on your way to finding the romantic partner you’ve been yearning for.

See what our students are saying about us.