Carey Gaynes
Dating and relationship coach in Chicago for singles
| Hourly rate range | $80 to $250 an hour |
|---|---|
| Focus areas | |
| Works with | Men and Women |
| Based in | Chicago, United States |
| Sessions | Online and in person |
| Practice | Coffee with Carey |
Carey Gaynes is a dating and relationship coach in Chicago. Carey helps single men and women learn to date with more confidence and understand the people they hope to attract. Carey worked as a matchmaker for many years before coaching. Carey also created the Coffee with Carey YouTube dating show, which began as a show for women over 50. Private clients come from Chicago and from cities across the country, including New York and L.A.
What Carey helps with
Carey helps people who feel stuck or unsure in dating. The focus is on building inner confidence and handling the outside challenges of meeting people.
- Breaking old dating patterns
- Becoming more approachable
- Building confidence in what you offer
- Understanding the opposite sex
- Feeling frustrated with online dating
- Stopping over-analyzing and self-doubt
- Learning about boundaries in dating
- Coming back to dating after time away
Who Carey works with
Carey works with both men and women from 25 to 75. Clients are singles who want to date well and meet the right people. Many are returning to dating and find it feels different from the last time. Private clients are based in Chicago and in other big cities.
Background and qualifications
Carey was a matchmaker for many years before moving into coaching. That work with matchmaking clients shaped the way Carey coaches today. Carey later started the Coffee with Carey YouTube channel, a dating show first made for women over 50. The response showed that men and women from 25 to 75 want the same talks about dating and relationships. Carey is based in Chicago and coaches private clients from New York to L.A.
Carey Gaynes pricing
Programs and services
- Private dating coaching
- Free introductory chat
- YouTube video series
Carey Gaynes reviews
The CoachVouch take
Carey is a longtime matchmaker who now coaches, and also hosts a dating show on YouTube.
Common questions
How much does Carey Gaynes charge?
Coaching with Carey runs $80 to $250 an hour. Message Carey from this page for an exact quote.
What does Carey Gaynes help with?
Carey Gaynes helps with breaking old dating patterns, becoming more approachable, building confidence in what you offer and understanding the opposite sex.
Does Carey Gaynes coach online?
Carey is based in Chicago, United States. Sessions are online and in person.
Does Carey Gaynes coach men as well as women?
Yes. Carey works with both men and women from 25 to 75.
Does Carey coach clients outside Chicago?
Yes. Carey is based in Chicago and also works with private clients from New York to L.A.
How do I contact Carey Gaynes?
Send Carey a message from this page. It's free and takes a minute.
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Last updated September 2026. Request a correction.