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He’s only 19 but One Direction heartthrob Harry Styles has had more headline-hitting flings than the rest of 1D put together. He was 17, she was 32 and the chemistry was ‘electric’ . Emma Ostilly – April 2012 Hazza moved on from Flack with 18-year-old American model Emma Ostilly during 1D’s stay in Auckland, New Zealand, last year. Lucy Horobin – August 2011 Harry Styles hit it off with married DJ Lucy Horobin in August 2011 when she grilled One Direction for Manchester-based radio station Key 103.Instead, it appears that Harry Styles and Cindy Crawford are old friends that like to grab a bite to eat together when they are in the same city.reported is that Harry Styles is still in a band with One Direction.Is this a sign that Harry Styles is dating older women again?As for dating older women, Harry Styles is noted for having a history with “cougars.” This is no stretch of the imagination, and, according to , Harry Styles has dated a long list of older women such as Lucy Horobin, Nicole Scherzinger, Emily Atack, Caggie Dunlop, and Taylor Swift.

The ' Live While We're Young' star's friend has told how they used to cause trouble in supermarkets and pretend he had Tourette syndrome - a condition which makes sufferers shout out things at random - as teenagers.

Things got hot and heavy with these two, but Horobin was reportedly married at the time and the reported fling with Harry didn't last.2.

Caroline Flack: Things continued to stay juicy when the hunky teen linked up with another older woman, 32-year-old Flack. Emma Ostilly: The singer was seen canoodling with the model (who is in his age range) in New Zealand.

Childhood pal Will Sweeney told The Sun newspaper: ' We'd act like complete idiots in public.

Harry would go into [British supermarket chain] Tesco, pretend he had Tourette's and walk around screaming and shouting.