Lucy Hale has been a fixture on our screens since the mid-2000s, but it was Pretty Little Liars that turned her into a household name. When you’re Aria Montgomery, people naturally start wondering if your real-life dating history is as dramatic as a TV show plot. Honestly, it kind of has been. If you look at who dated who, Lucy Hale has a list that spans from fellow actors and musicians to reality stars. She’s been incredibly open about some of these relationships, while others remained in that murky "are they or aren't they" tabloid territory for months.
It's not just about the names, though. It’s about how she’s navigated the messiness of dating in the spotlight. Unlike some stars who go into hiding after a breakup, Lucy usually keeps it pretty classsy. She’s talked about the struggle of finding someone who isn't intimidated by her success or the constant paparazzi presence. It's a lot. Let's get into the actual timeline because it's longer—and more interesting—than you might remember.
The Early Years: David Henrie and Alex Marshall
Long before the PLL craze, Lucy was a Disney kid. That’s where she met David Henrie. They were both on the rise, and they dated for about two years between 2007 and 2009. It was that classic young Hollywood romance. They were spotted at events together looking genuinely happy, but like most teenage loves, it eventually fizzled out as their careers started taking different paths.
Then came Alex Marshall. He was the keyboardist for the band The Cab. This was around 2010. They were pretty public about it, often posting photos together back when Instagram was just starting to become a thing. It felt very "indie-cool" at the time. However, by early 2011, things had gone south. Rumors swirled about why they split, but neither of them ever really gave a play-by-play. That’s a recurring theme with Lucy; she’s happy to share the good times, but she doesn't usually drag her exes through the mud when it ends.
The Chris Zylka Era and That Infamous Tweet
If we’re talking about who dated who, Lucy Hale and Chris Zylka is a chapter you can’t skip. This was 2012. Chris Zylka (who later went on to date Paris Hilton) was head-over-heels for Lucy. He even tweeted—yes, this was the era of oversharing on Twitter—that she was the most talented person he’d ever met.
But then, the breakup happened. And it wasn’t quiet.
Chris took to Twitter to announce they were over, and he didn't exactly hold back. When a fan mentioned Lucy, he replied with some pretty salty comments, basically implying she thought she was too good for him. He later apologized, saying she’s a remarkable woman, but the damage was done. It was one of those rare moments where the public got a glimpse into the friction that happens when one person’s fame starts eclipsing the other’s. Lucy, for her part, stayed silent. She didn’t bite back, which probably helped her come out of that situation looking like the bigger person.
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From Country Singers to Life Sentence Costars
Lucy has a thing for musicians. Or maybe musicians have a thing for her? In 2014, she dated country singer Joel Crouse. It was short-lived. Like, a few months short. They went to a Lakers game, they posted a few cute pictures, and then they were done. Busy schedules are the usual excuse in Hollywood, and for a rising country star and a busy TV lead, it actually makes sense.
She then moved on to Adam Pitts, the drummer for Lawson. This lasted about a year. They were very low-key. You’d see a paparazzi shot of them grabbing coffee or walking in London, but they didn't do the red carpet circuit as a couple.
Anthony Kalabretta: A Longer Stint
In 2015, things got a bit more serious with musician Anthony Kalabretta. This relationship was a bit of a roller coaster for the tabloids. One week they were "definitely over," the next week they were spotted at a Dodgers game looking very much together. They eventually called it quits for good in 2017. Lucy mentioned around this time that she was focusing more on herself and her sobriety journey, which she has been very open about in recent years. It’s a brave move to prioritize your mental health over a relationship that just isn't serving you anymore.
Riley Smith and the Life Sentence Connection
In 2018, Lucy starred in the short-lived but beloved show Life Sentence. She ended up dating her costar, Riley Smith. They were caught by photographers sharing a Valentine’s Day kiss, which is basically the official confirmation in celeb-land. It felt right—two actors working on the same project, spending 14 hours a day together. But when the show got canceled, the relationship seemed to wind down too. It happens.
The Skeet Ulrich and Colton Underwood Rumors
This is where things get a bit more "Internet Sleuth" style. In early 2021, the internet nearly broke when photos surfaced of Lucy Hale and Skeet Ulrich (yes, Billy Loomis from Scream and FP Jones from Riverdale) grabbing lunch and kissing. The age gap—he’s about 20 years older—had everyone talking. They seemed to have a very "cool, artistic" vibe together.
Was it a long-term thing? No. It was a pandemic-era fling that lasted about a month. Sources told E! News that they were just "hanging out" and it wasn't super serious.
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Then there was Colton Underwood. Shortly after his season of The Bachelor, before he came out, he and Lucy were spotted on a few dates. Lucy has always been a fan of The Bachelor franchise, so it seemed like a fun crossover. However, it never turned into a full-blown relationship. Looking back with what we know now about Colton’s journey, it’s clear they were just in different places in their lives.
What Lucy Hale Thinks About Her Dating History
Lucy is 36 now. She’s in a place where she’s not just dating to date. In various interviews, including her deep dive on the Diary of a CEO podcast, she’s talked about how she used to be a "serial dater." She admitted to seeking validation through men.
"I was always looking for something outside of myself to fill a hole," she basically said.
That’s a huge realization.
She’s spent a lot of time being single lately, and she’s vocal about how much she loves it. She has her dogs, her career, and a solid group of friends. She’s mentioned that she’s looking for a "partner," not just a boyfriend. Someone who adds to her life rather than someone she relies on for happiness. It’s a shift that a lot of women in their 30s experience, but seeing it play out with a celebrity makes it feel a bit more relatable.
The "Who Dated Who" Reality: A Timeline Summary
If you need a quick mental map of the who dated who, Lucy Hale journey, here is the rough breakdown of the confirmed and highly likely connections:
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- David Henrie (2007–2009): The Disney era sweetheart.
- Alex Marshall (2010–2011): The musician phase begins.
- Chris Zylka (2012): The dramatic Twitter breakup.
- Graham Rogers (2013): A brief summer romance.
- Joel Crouse (2014): The country music stint.
- Adam Pitts (2014–2015): The British drummer.
- Anthony Kalabretta (2015–2017): A more serious, multi-year relationship.
- Riley Smith (2018): The costar connection.
- Skeet Ulrich (2021): The "Internet-breaking" fling.
Why We Are So Obsessed with Her Love Life
People love Lucy Hale because she feels like a "normal" person who just happens to be famous. When she dates, she does it like we do—sometimes it’s a mistake, sometimes it’s a brief spark, and sometimes it’s a multi-year investment that doesn't pan out.
There’s also the Pretty Little Liars factor. Fans were so invested in "Ezria" (Aria and Ezra) that they desperately wanted her to date Ian Harding in real life. They never did. They are actually just really good friends. Lucy has had to navigate that weird space where fans are disappointed that her real boyfriend isn't her TV boyfriend. That’s a lot of pressure to put on any relationship.
Navigating Modern Dating Advice from Lucy's Journey
If you’re looking at Lucy Hale’s history to find lessons for your own life, there are a few key takeaways.
First, don't be afraid to be single. Lucy has shown that taking time off from the dating market can lead to massive personal growth and better mental health. She’s arguably more successful and radiant now than she was when she was constantly attached to someone.
Second, keep the drama private. Even when Chris Zylka went on his Twitter rant, Lucy didn't engage. In the age of "receipts" and "tea," there is a lot of power in silence. It protects your peace and your professional reputation.
Finally, know your worth. Lucy’s transition from dating whoever was around to being extremely selective shows a maturing sense of self-worth. She’s looking for someone who matches her energy, not just someone to fill the space on her couch.
If you’re curious about a specific era of her dating life, it’s worth looking at her social media from that time. She often expresses her feelings through music and subtle captions. But for now, the biggest "who" in her life seems to be herself, and honestly, we love that for her.
To keep up with Lucy's latest moves, you can follow her on Instagram or check out her recent interviews where she discusses her lifestyle and wellness routine. Staying informed through reputable entertainment news outlets like Variety or The Hollywood Reporter is always better than following unverified gossip accounts that tend to manufacture drama where there is none.