Jack Tracy Talks ‘History’ and Love

These 30-somethings are forced to confront complex issues such as gender roles, toxic masculinity, rejection, and loyalty. - Jack Tracy

The last web-serious I watched in its entirety is now an HBO hit show called Insecure. If I’m not mistaken Insecure is headed into its fourth season. Noah’s Ark was not a web-series, but a cable show I appreciated and one that showed camaraderie among friends by tackling real issues that we haven’t seen recently until now.

I had the pleasure of interviewing Jack Tracy, Executive Producer of an emerging gay web-series called History. Everyone should be talking about and watching it; it’s phenomenal!

Great news, the third season of History releases on Valentine’s Day! You have plenty of time to binge-watch season one and two so check them out.

The third season features six half-hour episodes and follows Tracy’s character, Jamie, as he discovers how the examples set by his parents framed his expressions of love and what he values most in relationships. The story picks up a year after the close of season 2 when the gang is finally all coupled up. Jamie is with Mark, a sexually charged Brit, and they are considering the possibility of opening their relationship, eyeing Will’s ex as a possible candidate. Meanwhile, Will is deciding whether or not to give in to his new boyfriend’s insistence they move in together while Matthew has decided to look past the gang’s objections and accept his boyfriend’s flaws. Then there’s Ted, whose own hang-ups may destroy his burgeoning relationship with a local drag queen.

“The struggles all of these 30-somethings face are a direct result of growing up gay,” explains Tracy. “They’re forced to confront complex issues such as gender roles, toxic masculinity, rejection, and loyalty. In the end, we learn what love is for each individual and whether the baggage from their past can ever be overcome.”

I wanted to understand why the web series is called History. Tracy shared with me that when you look back on your life you recognize patterns. In order to do better, you have understood this and work to break the cycle. In our lives, we sometimes form pathologies that are created from how our parents acted and reacted. We love the way our parents loved; we mimic what we saw. As the series progresses and dives further into the various storylines, juxtapositioning scenes from the past help us understand why the characters are the way they are.

As our interview progressed, I wanted to understand how much of Jack Tracy there is in Jamie, the main character. His response was, “It all depends on what season we’re referring to. Season 1 was like a 99% overlap. Season 2 was about 75% overlap and now as we approach season 3 it’s 50/50.”

Another reason I have been intrigued by History is the sense of diversity. I congratulated Tracy on achieving some diversity in his web series. He stated he would like to do more. He said the main cast is all caucasian men and shared that the script has black and Asian characters although very few non-caucasian folks auditioned. Tracy mentioned there are a lot of out of work white actors who have the wherewithal to explore volunteer opportunities. He also added there may be some level of hesitation of non-white actors coming forward to work on a gay web series. As we continued the conversation on diversity he stressed that he’s done well in some of his other productions such as a lead Filipino actor in his latest political thriller.

In the past, I steered away from web series because they never addressed the real issues we face in the LGBTQ community such as HIV and AIDS. When asked if it would be addressed Tracy chuckled and said, “Well, watch the next episode.” We learn that Jamie’s boyfriend is HIV+ and Jamie’s pre-existing fear in a pre-prep world needs to be addressed.

As someone who celebrates sexual freedom I was curious to know would any of his characters face any challenges in their sex lives since this season will be addressing patterns and how we possibly love the way our parents loved. Through the three seasons, we learn that Jamie does a lot of compartmentalization. He has his friends and he has his sex life and keeps them separate. He has issues of keeping everything in boxes. We may see him out with friends and he’s weirded out by the go-go boy but then he’s also throwing sex parties. Honestly I know several men who have that double personality type where they’re a prude in the street but they’re whores in the sack.

As I became more and more comfortable with our dialogue I began to understand the power of the series and why many of us are living this particular storyline. We are afraid to live or be like our parents.

When we discussed goals for this project and where he saw it going he said his goal is less specific to History and more about establishing his production company Necessary Outlet as a distributor and channel of LGBTQIA media where the characters come from the community but the stories have nothing to do with their LGBT status. He’s also been working on other shows such as a the comedies Big Law and Millennial Memoir.

As we were closing our delightful interview I wanted to know his thoughts on sexuality and asked what is one thing we should improve on as it relates to promoting sexual positivity. He said although we’ve made strides, he would like the community and society to work more on de-stigmatizing sexually transmitted diseases in general. We have no issues telling others and apologizing for having a cold but when it comes to STIs, we’ve been conditioned to be ashamed of sex so are often embarrassed and shameful if we’ve contracted an STI. Tracy said he’d like to see the day where we experience the same emotional response to an STI that we have with a cold and I couldn’t agree more.

Tracy has a partner but for fun, I wanted to know what his single friends would say or how they would rate dating in New York City. He said most would rate it as a five. He also mentioned he used to love dating and he would rate it a 9.

I enjoyed my conversation with Jack Tracy. He is a delightful man, serious, driven, and excited to share the newest season of the History web series.

As you get ready for the release of season 3 on Valentine’s Day, check out these recaps of season one and two.


Visionary Leader, Music and Hot Toddy Lover. After 15+ successful years in finance, I ventured out on my own, creating various brands, Flirtatious-T, Urban FLRT, Kinkster NYC, and now Milton Wes and OVAH MAG.