Blind Date Matchmaking in Chicago

We wanted to bring a fresh alternative to countless forms, contracts and hours of consultations. Matchmakers claiming they have thousands of daters, but none explaining from where. While other Matchmakers are forced to find your match at bars, the mall or other unsavory locations, we meet a fantastic set of new singles every week from our events alone, allowing us the opportunity to choose for you the best out of an already great crowd. We also garner extremely busy Matchmaking daters who find our services an efficient dating indulgence. Sought after for the level of dater we attract, the personal service we offer and an unparalleled selection of the daters you want to meet. We're honored to find that special someone just for you.

Consider us your blind-date specialists! Inspired by the romantic and simple days gone by, we bring back the lovely idea of meeting a date, arranged by another, at a venue of your choosing. All communication between you and your Date-Mate prior to your Date-Night will be entirely through us.

Include Me!

Join in on all the Cheeky fun by becoming a member! Enjoy the opportunity to be chosen for one of our fabulous Matchmaking Date-Nights.

Share your goals, preferences and details about yourself with our team and we’ll add you to our curated collection of daters.

Skip the line! While membership does not promise nor guarantee a set number of matches, members are given priority over event attendees who are invited to join our Matchmaking program. For those who desire a guaranteed number of matches; our Simplify-Me, Date-Me or Indulge-Me packages would suit you best.

$149 Per Year.

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Simplify Me!

Two pre-arranged Date Nights. For Each Date-Night you will meet a different partner chosen for you based on your mutual aspirations, expectations and likes.

Matchmaking by our experienced team. A comprehensive and detailed approach to understanding you and finding that partner who compliments both of your goals.

Our team will discuss your details and preferences with you upon confirmation.

Arrangements for each of your Two Date-Nights at one of our preferred venues or venue of your choice.

Complimentary admission to Speed Dating events at no charge to you for the duration of your Matchmaking package.

$595.

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Date Me!

Four pre-arranged Date-Nights. For each Date-Night you will meet a different partner chosen for you based on your mutual aspirations, expectations and likes.

Matchmaking by our experienced team. A comprehensive and detailed approach to understanding you and finding that partner who compliments both of your goals.

Our team will discuss your details and preferences with you upon confirmation.

Arrangements for each of your Four Date-Nights at one of our preferred venues or venue of your choice.

'This, that and the other' - the ultimate in concierge services. From fashion advice, unique date-spots to sought-after recommendations - ask and you shall receive!

Complimentary admission to Speed Dating events at no charge to you for the duration of your Matchmaking package.

$745.

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Indulge Me!

Six pre-arranged Date-Nights. For each Date-Night you will meet a different partner chosen for you based on your mutual aspirations, expectations and likes.

Matchmaking by our experienced team. A comprehensive and detailed approach to understanding you and finding that partner who compliments both of your goals.

Our team will discuss your details and preferences with you upon confirmation.

Arrangements for each of your Six Date-Nights at one of our preferred venues or venue of your choice.

Enjoy our 'This, that and the other' concierge service combined with a sampling of one of our Advice Packages. Spoil yourself in our insight and unparalleled experience.

Complimentary admission to Speed Dating events at no charge to you for the duration of your Matchmaking package.

$945.

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What information is exchanged with my ‘Date-Mate’ prior to our arranged date?

Prior to your arranged date, matched daters are only given each other's first names. After we consult with both daters, a night and venue is arranged with details of the venue, time and day of the meeting and the first name of your ‘Date-Mate’. Personal information such as e-mail, address or phone numbers are never exchanged by us and we urge our daters to use the same prudence.

Are events included in my Matchmaking Package?

Yes! A wonderful bonus to purchasing our Matchmaking Packages is the ability to attend our speed dating events at no additional charge to you. When you see an event you fancy attending - simply let us know and we'll add you to the guest list. There is no limit to the number of events you may attend with our compliments for the duration of your package. Attending events is an important part of the process and an excellent opportunity for us to get to know you better, for you to get to know our daters and for us to see who is drawn to you. As well, many Matchmaking daters find our events the perfect way to narrow down what they are looking for and learn a bit more about themselves in the process.

How can you charge so much less than the competition?

We don't have to spend money recruiting daters. We are sought after for who we are and the level of dater we attract, affording us the luxury of daters finding us, rather than the expense of having to find daters.

How do I let you know my preferences?

After you select your matchmaking package, you will receive a confirmation e-mail with details and questions to help us find your Date Mate. Tell us as much as you like! The more you offer, the better we can match. Our staff will review your preferences and get to work finding your match, making arrangements and sending you off on your date night.

Do I have to go to a venue or restaurant chosen by MyCheekyDate?

Of course not! You are free to choose any restaurant, venue or event you wish for your Date Night. Simply let us know what you have in mind so we may pass the reservation details onto your Date-Mate.

Am I obligated to use my Date Nights over a certain period of time?

You may use your Date Nights at your leisure.

What is the age range?

Our Matchmaking age range is similar to that of our events; our daters tend to be between early twenties to early forties.

What is ‘This, that and the other’?

Consider it our Concierge Service. Let us know what you need – everything from fashion tips to relationship advice, to being well-groomed. We have all the perks! Let us make your personal appointments or dinner reservations at the venue of your choice or ours - whilst you enjoy the lovely treatment.

What if I don't have the ability to act like a lady or gentleman?

Oh dear - how unfortunate. We do have a zero tolerance for any rudeness - of any sort. We attract such great daters but find - as in life - not every dater is ideal. Our daters are also our product and we go to great lengths to ensure everyone meets lovely daters. We want the right daters, not just any daters. Behavior short of lovely will result in a dater being banned from the company. This may upset some but we feel our daters as a whole appreciate the extra effort and we hope you do too.

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To read even more about our Matchmaking Packages - Click Here!

Check out our Press Page! - Click Here!

Need a bit of advice or guidance? From profiles to relationship coaching, learn more about our Advice Packages by Clicking Here!

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MyCheekyDate

For additional questions, feel free to contact us at [email protected]

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