Prince Harry painted the town red on Wednesday night, attending the birthday bash of society girl Anneke Gilkes in south west London. The 31-year-old was joined by his cousin Princess Eugenie, the Duchess of Cambridge's brother James Middleton, Holly Branson and Denise van Outen.
Two names that stood out on the guest list, however, were presenter Natalie Pinkham and blonde socialite Astrid Harbord. Both women have been linked to Harry in the past, when the Prince was in his twenties.
Harry and Natalie, who is expecting her second baby with husband Owain Walbyoff, were first linked in the summer of 2006, after pictures surfaced of the pair enjoying a night out together.
Prince Harry, pictured previously, was attending the birthday party of society girl Anneke Gilkes
At the time reports claimed that Harry was "infatuated" by the sports presenter, although Natalie has always maintained that she is simply a friend.
Shortly after Harry split with his first long-term girlfriend Chelsy Davy in 2009, the Prince was also briefly linked to Astrid, the daughter of late aristocrat Charles Harbord. Harry and Astrid, who now works in PR, were seen leaving an East London club together and climbing into a taxi.
Harry is known for remaining on good terms with his former love interests. For his 30th birthday party he invited both of his long-term ex-girlfriends Cressida Bonas and Chelsy to his celebrations.
A twenty-something Harry was linked to presenter Natalie Pinkham
His latest outing took the party-loving Prince to Battersea's Bunga Bunga club, to celebrate the birthday of society girl Anneke.
Harry is particularly close to Anneke's husband Charlie Gilkes, who co-owns the venue as well other drinking spots Maggie's, Bart's and Mr Fogg's in London.
Wearing a white shirt and navy trousers, Harry was seen making an exit at the end of the night, escorted by a couple of protection officers.
Harry and Charlie's friendship goes way back and in 2014 the royal attended Charlie and Anneke's wedding in Italy. Prince William's brother was joined by Princess Eugenie and Pippa Middleton, who dated the groom during their time at Edinburgh University.