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Nadine Leopold: Harry dated Nadine Leopold, a Victoria’s Secret model, this past year, but long distance and her perpetual fear that he was cheating drove them apart. Although it didn’t last for long, it did spawn a song (predictably) about Styles on Swift’s 11.

Apparently, she unfollowed fellow Angel Sara Sampaio after Sampaio spent a night partying with Styles. Erin Foster: After a few cozy lunch dates and a trip to the pumpkin patch, it looked like Erin might be Harry’s new May-December romance.

She’s also only a few degrees of separation from Harry’s former/maybe current flame, Kendall Jenner (more on that later)—Kendall is BFFs with Gigi Hadid, whose mother, Yolanda Foster is now getting divorced from Erin’s dad, David Foster (yes, that one)—got it? Kara Rose Marshall: Kara Rose Marshall was an aspiring model who rose to fame, post-Harry hookup. Emma Ostilly: Emma received a round of death threats from Directioners on Twitter after a picture of her kissing Harry surfaced to the point that she shut down her Twitter account; it also caused friction between her and her boyfriend (whose existence did nothing to squelch the rumor mill). Daisy Lowe: Model Daisy Lowe might be best known for making headlines when she announced that Gavin Rossdale was her father in 2004, but she’s constantly being romantically paired with pal Styles. Pandora Lennard: This alternative modeling agency founder, stylist, and creative consultant has been “just friends” with Harry for a while now, but sparked rumors in the New Year when she was spotted leaving his house in the wee morning hours. Kendall Jenner: Kendall and Harry were rumored to have an on-again-off again romance back in 2013; however, this holiday season, the two were spotted spooning and smooching on a yacht while on vacation.

Looks like Harry might be off the market (at least for now), ladies.

She starred in his video for his solo single, "Blowin' Me Up (With Her Love)." The two were spotted around a few times in 2002, but didn't flourish beyond that.

Ex-LFO lead singer Rich Cronin wrote "Girl on TV" for Hewitt in 1999, and I was always jealous of her for that.

The two met through their publicist and dated for about a year and half before calling it quits.

The early 2000s were famous for a lot of questionable things like bell-bottoms, pink-tinted glasses, and braided belts, but one of the greatest things to come out of the time were the ridiculous pop star couplings.

At the time, Britney Spears and *NSYNC were on the top of the world and bubblegum pop and boy bands were suddenly on everyone's radar.

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