Carey Gaynes
Dating and relationship coach in Chicago working with clients nationwide
| Hourly rate range | $110 to $250 an hour |
|---|---|
| Focus areas | |
| Based in | Chicago, United States |
| Practice | Coffee with Carey |
Carey Gaynes is a dating and relationship coach in Chicago. Carey helps people handle the dating world, understand the people they want to attract, and build inner confidence. Carey worked as a matchmaker for many years before coaching. Carey also created Coffee with Carey, a YouTube dating show that began with women over 50 in mind. Carey works with private clients across the country, from New York to L.A.
What Carey helps with
Carey helps people who feel stuck or unsure in dating. Carey works on old patterns, self-doubt, and the outside challenges of meeting people today.
- Breaking old dating patterns
- Building confidence in what you offer
- Understanding the opposite sex
- Handling online dating frustration
- Stopping over-analyzing and self-doubt
- Learning about boundaries in dating
- Becoming more approachable
- Dating again after time away
Who Carey works with
Carey coaches both men and women. Carey's YouTube show began for women over 50. Carey found that people from 25 to 75 want the same talks about dating and relationships. Carey works with private clients in Chicago and in other cities.
Background and qualifications
Carey worked as a matchmaker for many years. Carey says coaching is the part of that work that connected Carey with clients most. Carey later started the YouTube channel Coffee with Carey, a dating show first made for women over 50. The response showed Carey that men and women from 25 to 75 want the same conversations. Carey now coaches private clients from Carey's base in Chicago, including clients from New York to L.A.
Carey Gaynes pricing
Programs and services
- Private dating coaching
- Free introductory chat
Carey Gaynes reviews
The CoachVouch take
Carey is a longtime matchmaker who also hosts Carey's own dating show on YouTube.
Best for singles from 25 to 75 who want more confidence and a clearer view of dating.
Common questions
How much does Carey Gaynes charge?
Coaching with Carey runs $110 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, building confidence in what you offer, understanding the opposite sex and handling online dating frustration.
Does Carey Gaynes coach people outside Chicago?
Yes. Carey is based in Chicago and works with private clients from New York to L.A.
Does Carey coach men as well as women?
Yes. Carey works with both men and women between 25 and 75.
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.