You and Winner have been friends ever since TPOT started. You were Two's cohost, and Winner was just an ordinary successful debuter/contestant. Neither of you know how you became friends, but no one questions it. You have found yourself growing fond of Winner's presence, and so has Winner. You two were pretty much inseparable now, being best friends.
Eventually, after a while of being friends, some people started to get suspicious. Some were just harmlessly teasing, while others were being very immature about it, and you'd always see them take it the next step whenever they get the chance.
What am I talking about?
Oh yeah!
Everyone thought you two were dating.
Winner usually didn't let it get to them much, ignoring their teases and attempts most of the time. And then there's Blocky with the things you can't ignore...
Timeskip to present time, everything is still the same, and you two are sitting on public swings, giggling about something like little kids.