As Winston made his entrance, Twitter went into overdrive with users, including TOWIE's Bobby Norris, swearing they had seen the Essex boy's face before.
And they were right!
Reality TV pro Winston has already had a crack at being in front of the cameras taking a starring role in ITV2's last series of dating show Girlfriends.
Girlfriends sees three girls looking for love set out on finding the perfect partner, dating different guys as they go and finally choosing just one to take things to the next level. A shy and sweet Winston made it all the way to the final, but unlucky in love he was pipped at the post by another guy.
Now a far cry from his former self, the cheeky chappy oozed a little more confidence on yesterday's launch show even attempting to chat up the gorgeous Emma Willis (who he's met previously as Emma hosted the ITV2 show) before remembering she was married!
Heading into the house, Winston told viewers he thinks he's "a bit more switched on than the other Essex lads".
Appearing on the last series with Bobby Norris and Danielle Armstrong, Winston has even made a cameo in TOWIE - the show that has put his hometown on the map. His appearance was short and sweet as viewers saw the 27-year-old attempt to chat up the TOWIE girls but to no avail.
Maybe the charmer will have better luck with love in the house?
Last night saw ten new housemates enter the house, including fellow serial reality TV star Mark Byron, self-confessed power lover Tamara and strict catholic Danielle.
Six more will join the house in tonight's second show.
And we can't wait.
Watch Winston charm the ladies on Girlfriends below:
Check out the first group of housemates in the gallery below:
Copyright: Channel 5