Advising that “cuffing season” is a time to identify personal strengths and be honest about relationship goals, dating commentator Tre’ Amazing has provided insights into the dating scene since 2009. His organization, Ring|Side, started as a social gathering and has evolved into a digital community, live event platform, and YouTube channel. Also known as Troy Vaughan III, the YouTube entrepreneur spoke to rolling out about his journey.
Q: What inspired you to establish the organization Ring|Side?
A: [In] grad school, I was in a relationship with a woman who later became my wife [and] ex-wife. I had a close network of professional friends, including fraternity brothers and female friends. They often complained about the dating scene in Atlanta. My girlfriend and I decided to hold a “battle of the sexes” event. It was a networking opportunity for our single friends to meet and learn more about the opposite sex. We discussed topics like dating, long-term commitment, marriage, and sex.
We quickly received emails and messages from friends asking when the next event would be. They shared how they had met their partners at our event. This made me realize there was an interest in this genre. It affects men and women from all walks of life. This realization led to the birth of Ring|Side, officially incorporated in April 2011. Influenced by [famous] YouTuber DJ Vlad, I also decided to start conducting interviews.
Q: How did you come up with the name?
A: Ring|Side came about because I’m a [boxing fan] and full-contact sports. The debates we were having about relationships reminded me of a boxing match. The wedding ring symbolizes marriage, and we wanted to create an event around it. Are you trying to get into the ring? Are you trying to stay in it, or are you on your way out? The name is a double entendre, combining the boxing motif with the symbol of the wedding ring.
Q: What would you tell someone on your platform who had questions about cuffing season?
A: [Regarding] “cuffing season,” I would advise someone to identify their strengths and weaknesses. Are you a good talker? A good dresser? Good at networking? Use these strengths to meet the person or people you’re looking for. Be honest about what you want, whether a traditional relationship or something non-traditional. Find your tribe, the people who share your interests and desires.
Q: With your degree in public health, how do sex and relationships play a role in overall well-being?
A: As a public health graduate, I believe sex and relationships play a significant role in overall well-being. I focused my thesis on HIV prevention among heterosexual African American women. Even in 2024, HIV and AIDS are still [significant] issues. Knowing your status, getting tested, and being honest with potential partners is crucial. This is how I merge the two genres of public health and relationships.
