Chicago is a city of ambition, energy, and unexpected charm. But when it comes to dating in Chicago, it can feel more complicated than it should. Between packed schedules, unpredictable weather, and a social scene that often leans casual over committed, many singles find they’re meeting plenty of people, but not the right ones.
Sophy Love is here to change that. We work with singles in Chicago who are ready to move past the noise and into a real, lasting partnership. Whether you’re in Lincoln Park, West Loop, River North, or Evanston, we bring structure and insight to your dating life. With a background in psychology, years of coaching experience, and a sharp eye for compatibility, Sophy helps you get clear on what (and who) you really want.
Our services include executive matchmaking, date coaching, and private dating concierge support, all rooted in the principles of conscious matchmaking. From Fortune 500 professionals to creative entrepreneurs, we help you move past the noise and toward someone truly aligned with your values.
You don’t need another dating app. You need a smarter, more human way to connect. And you’ve come to the right place.
Meet Executive Singles in Chicago
Sophy Love is not a dating app. We are a relationship-focused matchmaker in Chicago, working exclusively with emotionally available, intentional singles who are ready to meet their person.
Discover the Best Matchmaker in Chicago for Real Connection
Chicagoans know how to hustle, but when it comes to love, you deserve ease. If you’re done with surface-level swiping and want something deeper, Sophy Love is here to guide you through a more grounded, human, and intentional way to date.
Our founder brings deep psychological insight, years of experience, and a no-nonsense approach to conscious dating. Whether you’re looking to reset your patterns or just want better options, we offer support, structure, and the confidence that you’re on the right path.
We don’t just introduce you to people, we walk with you through the process. From the Gold Coast to Hyde Park, Oak Park to Wicker Park, we help Chicago singles meet matches who are as serious and soulful as they are.
Ready for dating to feel different? Sophy Love is here.
Success! I met my husband on the second match that Sophy set me up with. It was an instant connection. Sophy was fantastic! She was kind, always available, and most importantly she truly listened to what I felt I needed and wanted. The fact that she took the time to get to know me gave me more hope and comfort. Honestly, she could not have found me a better partner. I am now happily married with a baby girl. I really love my family. Thank you Sophy!
Sophy has taught me how to brave the dating world with no fear, no reservations, and no ego. I feel reassured that we are getting closer to finding my perfect match and I couldn’t do it without her.
It takes great care and ability to bring together two people who are searching for one another. The attention to detail from start to finish, the pep talks, the honest encouragement and quality of introductions truly set Sophy apart!
Sophy has an intuitive nature. She is able to understand a person as if you were an old friend, in a rather remarkable fashion. She is kind, empathetic, accommodating, and a true ally in the scary world of dating. I feel that she actually listens to my concerns and her dating pep talks are the best! She is converting an exhausted dating cynic into an actual optimist.
Sophy = matchmaking done right. I imagine matchmaking done right is a challenging job, Sophy handled it with ease. Sophy is an awesome communicator and pays attention to detail. Finding a connection isn’t easy, but Sophy does all the heavy lifting and makes it fun in the process.
Sophy has been an amazing matchmaker. This is my first time using any matchmaking service, and she has been there for me on so many levels. I don’t have to swipe, vet or negotiate – she listens to what I’m looking for in a partner and goes out of her way to make sure I’m satisfied. This has been an extremely positive experience, and it’s wonderful for people like me who are too busy and too old to keep swiping!
Sophy is amazing! She came highly recommended from a friend and did NOT disappoint! I felt like she has a tremendous gift for listening and understanding what I was looking for in a future husband. And she delivered him as my first match! We hit it off from our first date and truly believe we are soul mates. We’ve been together for over a year and a half and recently bought a new house together with a wedding in the near future! I highly recommend Sophy if you’re serious about finding the partner you’ve been waiting for!
I had been divorced for a number of years. I thought I was fine by myself: I had friends, and activities, and I was happy. But I was encouraged to take a chance, and rather than put myself on the internet, I found Sophy. She was easy to open up to and helped me to really think about what was important to me moving forward. She encouraged me to be open to the new experience of dating and she always listened. On the second “date” that she set up, I met my fellow and we talked for hours. We connected in so many ways that we knew we were the “right fit.” We haven’t been the same and we never will be. It has been two+ years and on the anniversary of our first date, we send a text to Sophy and thank her for putting us together. Thanks Sophy, you have shown us our happy place, and it is brilliant.
Sophy listens to your story with compassion and kindness. Under her guidance, you feel less alone navigating the overwhelming and intimating world of dating (both online and in person). Ask Sophy for help, you won’t regret it…it could truly be the first step you take to finding that great love you have been searching for!
In working with Sophy, I felt like I was speaking with a good friend who had my best interests at heart. She took the time to get to know me, and where I was struggling. Our conversations were fun, educational, and supportive (even when they included some tough love). Most importantly, they involved thoughtful reflection, forcing me to articulate my feelings about dating in a way that I never had before. All of this helped me learn a lot about myself, and what qualities actually mattered to me in a prospective partner. Now I’m in the healthiest, happiest relationship of my life, and I firmly believe this would not have been possible without Sophy!
The course was one of the most powerful workshops of my life and it was exactly what I needed. I’ve been putting the practices into my life and watching the results show up almost everyday. It’s incredible. The work is like a key that is unlocking my life and allowing me to blow by blockages that I’ve tripped over for years. So again thank you, thank you, thank you.
At the Closer workshop, Ryel paired us up, and took us through guided questions meant to dig deep and really get to know one another. By the end, I felt like I hadn’t made meaningless small talk and that I hadn’t been robotically evaluating people with checklists, but instead getting to know them IN REAL LIFE. Since the workshop, I’ve been a lot more honest with the people I date, instead of hiding my emotions or trying to be someone else who has different preferences.
It’s impossible to learn how to build deeper connections alone, which is what makes Closer workshops so special. It’s the perfect way to practice showing up as your most authentic self with a group. Ryle creates an atmosphere that’s both fun, and educational which really helped me connect to myself while Sophy curated a group of like minded people. I came away with a few fun dates and a couple new friends.