Harry Styles is known for being a ladies man, so it's not surprising that he could run in to two of his former girlfriends at the same time.
At the British Fashion Awards, held at the London Coliseum on Monday night, The One Direction heartthrob bumped in to ex-girlfriends Kendall Jenner and Cara Delevinge.
The 20-year-old was about to make his way down the stairs when he encountered the two models at the top, who happen to be close friends.
The brief exchange appeared slightly strained at first, but any ice was broken and all three started smiling and laughing.
The One Direction singer reportedly had a passionate tryst with Delevinge for several months back in 2013 before her agency told her to cool it off as they considered him "too low-rent" for her image.
Styles then went out with Jenner, 19, who was said to be smitten with the British star but things allegedly turned sour when he stopped returning her calls and was then pictured with another women.
The Burberry model, 22, who is known for being friends with most of the famous ladies in the fashion world including, Kate Moss and Rihanna has become close with Jenner over recent months.
The supermodels were pictured close together for most of the evening with Jenner laughing hysterically the whole time.
Delevinge, who was awarded Best Model during the evening wore a white dress with black louboutin sandals.
The younger sister of Kim Kardashian opted for a white and black cat suit with her hair loose and a slick of red lip stick.
Harry, wore a striking two-piece navy Lanvin suit with red pinstripes and black shoes but despite turning many heads he reportedly only had eyes for Emma Watson at the show.
Another of the star's famous ex-girlfriends, Taylor Swift, is also in London at the moment. She allegedly hopes to rekindle her relationship with the star.
The 24-year-old, will be performing at the Victoria's Secret Fashion Show which is taking place in the capital on Tuesday.