For the longest time, Ashlee Simpson was merely Jessica Simpson’s younger sister. Jessica, a blonde bombshell with the voice of an angel, eclipsed Ashlee in beauty, success, and popularity. However, in the early 2000s, Ashlee began to find her way out of the shadows.
Ashlee burst out onto the scene with a killer album, Autobiography, and a reality TV show, The Ashlee Simpson Show, in 2004. Through her music and daily life, Ashlee showed audiences that she’s just as talented as Jessica. Embracing a darker, edgier sound and style (and coining herself the “black sheep” of the family), Ashlee set herself apart from her sister. Ashlee went on to excel in the alternative rock world.
Ashlee also found much success in love. From flings to full-fledged relationships, Ashlee has an extensive romantic history. Let’s take a look at the lucky guys she’s dated!
15 Josh Henderson
Ashlee Simpson’s first real boyfriend was Josh Henderson. He’s an American actor who never really blew up in terms of fame and fortune. His most notable roles were on Desperate Housewives and Dallas. Although they didn’t last, Ashlee and Josh were perfect for each other at the time—sweet, young, and innocent.
14 Carson Daly
Now, Carson’s a little tricky. Ashlee is rumored to have dated Total Request Live’s (TRL’s) host, Carson Daly; however, there’s still some confusion surrounding how serious they actually were. Was this a fling or an actual relationship? The truth remains a mystery. All that’s certain is that they didn’t last.
13 Gregory Smith
Gregory Smith was the ultimate dreamy teen actor in the early 2000s. He starred in Xenon: Girl of the 21st Century and Harriet the Spy. Ashlee was obviously taken with him, and the two had a solid relationship for a relatively short period of time. Ah - young long never lasts.
12 Nick Carter
There’s a nasty little rumor claiming Backstreet Boys’ Nick Carter cheated on then-girlfriend Paris Hilton with Ashlee! Yes, Ashlee Simpson is a notorious flirt—but would she ever be the other woman? The mystery remains unsolved; however, Ashlee’s flirtatious ways and Nick’s womanizer reputation strongly suggest it may be true.
11 Kelly Slater
Ashlee has had to deal with so many rumors about her love life! Next on the list is another uncertain linkage with Kelly Slater. Apparently, these two met on the beach and had a summer of love. She just couldn’t resist those piercing blue eyes! Who knows whether that fling was true.
10 Ryan Phillippe
Ashlee Simpson and Ryan Phillippe were definitely seen flirting and giggling on a club date in Hollywood. They looked quite cozy over drinks and conversation. Ashlee and Ryan’s relationship didn’t seem to go much further than that, so Ashlee was obviously still living the young and single lifestyle.
9 Tyler Hoechlin
Ashlee Simpson met Tyler Hoechlin while filming 7th Heaven. This was obviously an on-set romance because the two barely lasted two months. While Ashlee ended up soaring to success after her stint on the show, Tyler didn’t go too far after that. He mostly remained in the supporting actor category.
8 Ryan Cabrera
Ashlee and Ryan had known each other for a long time and they were friends, but Ashlee took things to the next level by kissing Ryan while they were rollerblading. Ryan Cabrera was definitely one of Ashlee’s great loves. Evan Ross, Ashlee’s current husband, even asked for Ryan’s blessing to date Ashlee.
7 Wilmer Valderrama
Although Wilmer Valderrama shouldn’t be considered one of Ashlee’s great loves, the two were certainly a high-profile couple. Having just broken up with the troubled teen star, Lindsay Lohan, Wilmer jumped right into a relationship with Ashlee—garnering much attention for doing so. Apparently, Ashlee’s song, “Boyfriend,” is about that whole situation.
6 Braxton Olita
Braxton Olita was a guitarist in Ashlee’s band, so the couple spent tons of time together; however, these two didn’t last long. Apparently, Braxton didn’t like that Ashlee had plastic surgery. He liked the way she used to look. Moreover, Ashlee had her eyes on someone else…
5 Pete Wentz
After leaving Braxton, Ashlee headed straight toward Fall Out Boy rocker, Pete Wentz and the two ended up getting married! From 2008 to 2011, Ashlee said “goodbye” to all her flings and settled down. She became a wife and a mother to Bronx Mowgli Wentz. Unfortunately, the couple eventually parted ways.
4 Vincent Piazza
Ashlee Simpson dated Boardwalk Empire’s Vincent Piazza after divorcing Pete Wentz. The two stayed together for a little over a year. Although Vincent seemed like a good, mature option, he spent a lot of time working. Rumor has it the two split up because they couldn’t spend enough time together.
3 Colin Egglesfield
Ashlee and Colin Egglesfield met while filming Melrose Place. The two would flirt incessantly in between scenes. In fact, their flirting supposedly irritated Pete Wentz while he and Ashlee were married. Perhaps Colin and Ashlee were just flirt buddies; however, flirting usually hints at much deeper feelings below the surface.
2 Craig Owens
Craig Owens, from the band D.R.U.G.S, was another match Ashlee made after divorcing Pete Wentz. Whereas Ashlee’s flings are usually quite lighthearted, her relationship with Craig was a bit grimy, as Craig was a good friend of Pete's. It seemed like Ashlee was using Craig to make Pete jealous.
1 Evan Ross
After years of frequent on-and-off boyfriends, flings, and rumors, Ashlee finally settled down with Evan Ross in 2014. The two seem incredibly content—having gotten all the youthful partying out of the way. they simply enjoy family life. Ashlee and Evan have one child, Jagger, and another on the way!