My answer to this won’t be very different from what everyone else thinks 🙂
I do believe they were kind of together in the 90s. My theory is that Gillian thought they were in a relationship, David thought it was just casual and kept having other affairs and finally ended up marrying Téa without telling Gillian, and breaking her heart. That’s basically my headcanon for what happened between them in the 90s.
Then, I think they reconnected during IWTB in 2007/2008, I think Gillian was there to support him when he needed and they became good friends again, until 2011 / 12 when they both became single at the same time and decided to give it a real shot. Which happened ‘til 2016 and… here we are…