Coaching Programs & Packages for Chicago Singles

Advice Simplified

Dating is hard. We all know this. Fraught with self-doubt, rejection and insecurity. Whether you are entering the world of dating and need assistance with ensuring your profile and presentation are optimized for the best results, navigating the difficult waters of new dating endeavors or in a long-term relationship and seek guidance and feedback on how best to ensure relationship success and gain clarity – we can help. Taking a simplified approach to the most complicated of matters. ~~

Powered by the relationship experts at MyCheekyDate, we know first hand the challenges daters face. With over 13 years of personal matchmaking experience, helping singles from across the world, with all the emotion, struggles and frustrations dating can bring. Our intimate experience with hundreds of thousands of singles, allows us a unique insight into an ever-evolving and changing dating landscape. We understand what it takes to find personal success and achieve your dating and relationship goals.

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Profile Me!

For those newly single or being reintroduced to dating and putting themselves out there online, the Profile Me! package will help start you out in the right direction and avoid some of the common pitfalls we have seen and experienced over the years. The wrong picture or series of pictures, misdirected or misguided profiles or poorly reflected representations can make the difference between dating app & online success or crickets. Perhaps you are breaking one of the cardinal rules of dating apps and don’t even know it! Enjoy a comprehensive overview consultation of your online profiles from dating apps to social media. Let our specialists advise, recommend and set you on your path to maximum results.

90 mins – $159.00

• Ninety minutes of video chat or phone consultation including a comprehensive overview of your online profiles, from dating apps to online presence.

• Tips and advice on improving your profile strength and appearance.

• Dating Profile Optimization.

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All About Me!

If you are finding that you are connecting with other daters but often feel like your potential relationships plateau at a certain point, All About Me! is a fantastic addition to your dating mindset. Let’s navigate through how you are approaching your dates, your challenges in reaching the next step in your dating life or how are you are maximizing the chances of furthering relationship opportunities. All About Me! can help take your relationships to the next level and end the frustration of connections fizzling out before you have had an opportunity to showcase yourself in your best light. Included in this package, should you wish, are all the insights and benefits of the Profile Me! package along with detailed appearance advice, communication tips ranging from text & DM etiquette to learning how and when to communicate best. A fantastic package to take advantage of all the elements mentioned or simply to focus on certain key factors you feel are keeping you from reaching that next dating level.

3 Hours – $295.00

• All the insights and benefits of the Profile Me! Package.

• Included in this package, with a comprehensive overview of your online dating presence.

• 3 Hours total of one-on-one consultation time – video chat or phone.

• Detailed, insightful and goal-oriented one on one discussion with one of our advisors, about your current dating life.

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Relationship Me!

When you find yourself dating exclusively or in a long-term relationship, you soon realize so much of the anxiety, confusion and questions you thought were in your past life of being single – have only just begun. Perhaps you are finding yourself bouncing from relationship to relationship – wondering is it me? Where am I going and who is going to go with me? The Relationship Me! package is the perfect opportunity to work on you and gain clarity on specific issues you may find yourself struggling through, get help in the small missteps that are leading to larger problems or allow us the opportunity to assist in creating healthy mind and lifestyle patterns. Advice tailored for you today, not spread out over years of endless couch appointments. When it comes to dating and relationships, we believe that the parameters and approach changes on a weekly, sometimes daily basis. Our guidance is the result of 13 years and hundreds of thousands of personal experiences with our daters, their revelations and their successes shared with us. We are their matchmakers, coaches, friends, shoulders and champions. Let us show you why we are are trusted by so many.

4 Hours – $345.00

• All the benefits of the Profile Me! and All About Me! Packages, if desired.

• Up to 4 hours total of one-on-one consultation time – video chat or phone.

• This package is best suited for those seeking relationship advice and have evolved from regular dating.

• Let our staff guide you through the right steps to elevate your relationship experience and longevity.

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How It Works

Simply select the package that is right for you. Whether it is our Profile Me! Package, perfect for singles seeking dating profile optimization, our All About Me! Package for those interested in a guiding touch to get them to that next level of dating success or our Relationship Me! Package for those looking for curated, personal and experienced advice to help with dating and relationship challenges, pitfalls and goals.

Upon registering, you will be contacted by one of our team who will assist you with your next steps. Any questions, concerns or thoughts you may have – simply reach out to us. We would love to hear from you. Once we have had the opportunity to learn about you, we can then start to set up a time for your one-on-one online or telephone sessions. You can choose to speak with your dedicated team member via our own customized and private online platform or you may prefer to speak on the telephone instead.

You will find our packages are guidelines to help you find the best avenue for your goals. We appreciate every situation and person is different and are accustomed to all types of dating and relationship problems, frustrations and situations. Your time with us is one in which you should feel free to be open, honest and forthcoming. You will simply not find a more understanding, relatable and caring ear. If you are unsure if your particular situation is one in that we can assist – please feel free to reach out to us prior to your purchase.

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What is MyCheekyAdvice?

MyCheekyAdvice is a Dating & Relationship advice site born out of 13 years of Dating & Matchmaking experience at MyCheekyDate. Over the years we have inspired hundreds of thousands of our daters to believe in themselves, who in turn have inspired us with their shared personal experiences, their trials and tribulations and their never-ending perseverance. Our approach has always been that of a personal one. Taking the time to get to know our daters through our amazing and worldwide dedicated team has uniquely positioned us to assist any dater from all walks of life.

What makes your staff so knowledgeable?

Working one on one with dater’s every day is what our staff does best. Through our Events and Matchmaking services at MyCheekyDate, our staff not only assist dater’s personally everyday in their search for relationships, but they also work with countless daters as they navigate through the relationships they formed through our services. It is our personal, intimate and trusted relationships with our daters that make us the premier resource for dating advice.

I’m an active dater, how can MyCheekyAdvice benefit me?

When it comes to dating and relationships, we believe that the parameters and approach changes on a weekly, sometimes daily basis. What was appreciated yesterday may not be relevant today. Dating in the 21st century changes rapidly from day to day and person to person. Gone are the days of hard and fast rules and only one way to date. The multitude of ways to date has leveled the playing field in terms of every dater having their own choice on how they meet people and the pace of how each relationship is developed.

Will I be communicating with a licensed therapist?

While our staff have varied advanced educational backgrounds, it is their first-hand experience with singles that sets us apart. What they don’t know about dating isn’t worth knowing. With decades of cumulative experience in the dating industry, our staff work one-on-one with daters every day. Their empirical wisdom serving thousands and thousands of daters is second to none. There is simply no substitute for experience and while we believe any form of self-help is invaluable, often times such dating and relationship advice is given under the lack of experience needed to properly ascertain, assist and benefit daters properly.

How is it determined when I have my sessions?

Once you have registered for your desired package, our staff will be in touch with you to schedule your session/s. Together, we will work to find the best times that work for your schedule.

What if I still feel like I need more assistance after my package is complete?

We understand that working on yourself, your profile, mindset and approach can very much be a journey and not a definitive destination. Once your package is complete, you may discuss purchasing additional time to discuss your continued needs with our staff.

Are the advice packages all inclusive and available for all sexual orientations?

MyCheekyAdvice and MyCheekyDate are proudly all-inclusive. No matter your orientation, our team has the empirical experience and enviable ability to assist daters from all walks of life.