Ollie is first seen managing the guest list for Amber Atherton's jewellery range launch party at Raffle's. The next day, Alexandra "Binky" Felstead invites him and Cheska Hull to her mum's cottage in East Sussex for Sunday lunch, though he has to hurry back to London for date night with girlfriend Gabriella Ellis. Having joked about the candle at their table going out, talk turns to their relationship, with Gabriella professing her strong feelings for Ollie, which he reciprocates when asked. He quickly diverts the conversation however. Further cracks begin to show when the two have different ideas of his twenty-fourth birthday celebrations. Ollie suggests doing something as a big group, while Gabriella thinks they should spend it alone on a skiing trip. Ollie agrees, but invites Binky and Cheska anyway to join them in Chamonix, to Gabriella's visible frustration.
- Series 1, episode 1: "Ad Victorem Spolias – To The Victor Go The Spoils", 60 minutes, E4, aired 9 May 2011
|Current cast members|
|Francis Boulle • Fredrik Ferrier • Mark-Francis Vandelli • Louise Thompson • Jamie Laing • Victoria Baker-Harber • Oliver Proudlock • Alex Mytton • Sam Thompson • Sophie Hermann • Georgia "Toff" Toffolo • Tiff Watson • Olivia Bentley • Frankie Gaff • Ryan Libbey • Julius Cowdrey • Ella Willis • Daisy Robins • Mimi Bouchard • Sam Prince • Harry Baron • Charlie Mills|