Featured Image Credit: Getty
Topics: Celeb Breakups, Celebs, Entertainment
Sarah Halle Corey
I’m kind of a rom-com connoisseur (rom-com-oisseur?) and after countless hours of happily ever afters, I’m ready to make a proclamation: Pretty Little Liars star Lucy Hale is in the running to be this generation’s rom-com queen. Yup, I said it. Just one look at her resume from the last few years with movies like The Hating Game, Puppy Love, and Which Brings Me To You, and it’s clear she’s going for rom-com gold on screen. But is her real life off-screen just as romantic? That requires a little more examination.
On March 12, PEOPLE confirmed Lucy is dating Too Hot To Handle star Harry Jowsey. A source said the relationship is “super casual, but it’s not brand new.” So it sounds like Lucy is in a situationship with a guy whose Perfect Match co-stars straight-up called a “fuckboy.” Not exactly the stuff of great romances, but hey, if it makes her happy, who am I to judge?
In 2023, Lucy went on Rachel Bilson’s podcast to talk about how she was done going after the wrong guys. “I’ll die alone before I settle. It’s so dramatic, but that’s just how I feel.” She also said she has a history of looking at her boyfriends as project to work on. “I typically liked a little project to fix, like, your problems are worse than mine, so you’re gonna make me feel better about myself just because I’m helping, you know, ‘fix you,” she said. Now, I don’t know if Harry is an example of one of Lucy’s projects or of her refusing to settle, but I guess time will tell.
In the meantime, let’s take a look at Lucy Hale’s dating history to see if her real life has been like a real rom-com.
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Lucy’s first major relationship was a true teen dream. She dated Wizards of Waverly Place star David Henrie for two years, from 2007 to 2009.
Although they never officially publicly dated, Lucy did write the song “Lie A Little Better.” about her crush on her Pretty Little Liars co-star Drew Van Acker. Unfortunately, their love story never grew beyond Lucy’s love song.
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In 2012, Lucy and actor Chris Zylka dated for a little under a year, but their breakup was super messy. Chris made his bitter feelings very public when shortly after the split, he tweeted: “Don’t have a girlfriend — she decided she was too good.” Lucy leaving a trail of broken hearts!
Lucy dated country singer Joel Crouse for a few months in 2014, but they had to do long distance and it was too much of a strain on them.
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Soon after her breakup with Joel, Lucy moved on to Lawson drummer Adam Pitts, but they broke up in spring 2015.
Lucy’s string of musician boyfriends continued with Anthony Kalabretta later in 2015, but they called it quits in January 2016.
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After spending 2015 with just musicians, Lucy went back to her roots and dated an actor. This time, she had a showmance with her Life Sentence co-star Riley Smith for much of 2018.
During the pandemic lockdown in 2020, Lucy and former Bachelor Colton Underwood tried dating. It didn’t work out, which makes sense, since Colton came out as gay in 2021.
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In 2021, Lucy gave an age gap romance a try by dating Riverdale star Skeet Ulrich, who’s 20 years older than her. It only lasted a few months, leaving Lucy ready to move on to her next rom-com moment.