Got a single friend who's a total catch? It's time to play matchmaker with a twist! Create a slide deck presentation that showcases their best qualities, quirks, and charm. Then, take the stage and deliver a 3-5 minute pitch to a room full of eager singles ready to mingle. Who knows? You might just spark the next great love story!
Tickets:
$25-35 to Attend: Attend as a guest and enjoy the pitches (no pitching required)
$70 to Pitch: Includes a 3-5 min pitch slot and x2 entry tickets. (Request to pitch here)(opens in a new tab)
*Note: Pitch & Pair will email you access to purchase pitch tickets, if approved.
Only Pitch tickets include a pitch spot—Entry tickets are for watching only. Pitch tickets are only sold from the waitlist.
Our shows feature a balanced mix of male and female participants being pitched. However, as this is a general admission event, we can’t guarantee the gender balance of the audience.
*Please note this is a 21+ event
What to Expect
Pitch Your Friend: Sign up to present your single bestie using a slide deck. Each pitch is 3-5 minutes and designed to highlight their best qualities, quirks, and what makes them a total catch.
How It Works
Tickets: Buy your tickets early to reserve your seat. Join the waitlist to purchase a pitch spot.
Presentations: Present your friend to a room full of singles or sit back, sip your drink, and enjoy the presentations.
After each presentation: There will be a Q&A session, and presenters will share their friends contact info (e.g., Instagram handle) on the last slide so audience members can slide into their DMs
Mingle & Match: After the pitches, you can also mingle and make connections with anyone who caught your eye!
Why Choose Pitch & Pair?
Tired of endless swiping, awkward first dates, and traditional speed dating? At Pitch & Pair, we’re flipping the script on singles events with a fun, interactive matchmaking experience where friends pitch their single besties to a room full of eligible singles. Forget dating apps, this is a creative, real-life way to meet, mingle, and make authentic connections!
Featured on: ABC, NBC, CBS, Today Show, Good Morning America, VICE, New York Post, Cosmopolitan, Glamour Magazine, Time Out, The Late Show with Stephen Colbert
Creative Matchmaking: Your BFF knows you best, and their pitch might just spark your next great connection.
Fun & Interactive: Laugh, mingle, and connect with singles in a lively, welcoming environment.
Authentic Vibes: No filters, no awkward interviews, just real people making real connections.
Testimonials
“Pitch and Pair is an ingenious idea perfectly executed. You should go without hesitation-whether you’re the potential object of romantic desire or the pitcher or even a spectator, it really does make for an immaculate evening.” -Alex R.
"I had a great time and got 3 dates from my friend's pitch and pair presentation!"– Doug,
"It was a blast presenting my friend at Pitch and Pair. It was so fun, creative, and funny." – Marissa,
FAQs
Who can attend? Anyone 21+! Whether you’re pitching a friend or just here to watch and mingle, there’s a spot for you.
Do I have to pitch someone? Not at all! You can attend as an attendee and see if anyone catches your eye.
How do I get a pitch spot? Pitch spots are selected from the waitlist, you can join our waitlist here: Request to pitch here.(opens in a new tab)
More Info? www.pitchandpairnyc.com
Mingle & Meet: Not pitching? No problem! Grab a drink, enjoy the show, and chat with other eligible singles in a relaxed, fun setting.
Connect IRL: Witness connections come to life in real time—whether it’s sparks of romance, the start of a new friendship, or a wingman/woman hyping up their bestie.
Spots are limited—grab your ticket now and let the matchmaking magic begin! Who knows? Your next great connection could be just one pitch away. At Pitch & Pair, we’re redefining the singles event scene with a fresh, fun, and interactive approach to matchmaking. Say goodbye to swiping and awkward speed dating—our dating event is all about creating meaningful connections with humor, charm, and creativity.
Friends pitch their single besties to a room full of eligible singles in a unique format that’s as lively and authentic as Chicago itself. Whether you’re looking to meet new friends, connect with strangers, or enjoy a memorable date night, this is one of the most exciting things to do in the city’s dating world.
Join us and see why Pitch & Pair is the most talked-about event for singles. It’s more than a dating event—it’s a night of laughter, connection, and maybe even love! #SinglesEvents #SpeedDating #DatingEventChicago #MeetNewFriends #ThingsToDoChicago #DateNight
Note: Our events will be recorded for media and social use. By attending, you agree that any recordings or photos may be used for promotional purposes without compensation.
NOTICE OF FILMING PHOTO RELEASE
This area is being used to film an audiovisual production for Joerky LLC d/b/a Pitch and Pair (hereinafter, “Producer”)
By your presence in this area, you acknowledge that you have been informed that you may be photographed and recorded as a part of an audiovisual production. Further, by your presence in this area you hereby irrevocably, freely, and without restraint consent to and grant to Producer and its agents, licensees, and assigns (collectively, “Owner”) the unrestrained right, in perpetuity, to utilize your name, likeness, mannerisms, and voice in the audiovisual production without compensation and/or credit and for such production to be exploited in any and all media worldwide in perpetuity. Owner shall have the unrestrained right to own, utilize, or alter the footage captured in this location, in any manner Owner sees fit and for any purpose whatsoever, all of the foregoing to be without limitation of any kind. You hereby authorize and grant to the Owner the unrestrained rights to utilize the footage captured at this location in connection with the audiovisual production, including, without limitation, in its advertising, publicity, public performance, and exhibitions thereof. You hereby stipulate that the footage captured at this location is the sole property of the Producer to do with as it will.
You hereby waive, to the fullest extent that you may lawfully do so, any causes of action in law or equity you may have or hereafter acquire against the Owner which may arise out of or in connection with the utilization by the Owner of the footage captured at this location and/or of the audiovisual production, including, without limitation, for libel, slander, invasion of privacy, copyright or trademark infringement, right of publicity, or false light.
The Den Theatre and comedy club is pleased to host Pitch and Pair on April 23, 2026 at 1331 N. Milwaukee Ave. in Chicago’s Wicker Park neighborhood.
Tickets are currently available at thedentheatre.com or by calling (773) 697-3830.
