Today marks 33 years that Justin Timberlake has graced the planet.

And in those awesome/talented/swoon-worthy years, the birthday boy has wined and dined a lot of Hollywood ladies.

To honor JT’s special day, we’re taking a look back at all of his high-profile romances.

Let’s just say he had a lot of practice in the relationship field before putting a ring on Jessica Biel‘s finger!

Fergie: Circa 1996

Long before he was JT and waaay before she was rockin’ it out onstage with the Black Eyed Peas, the pair were an item.

He was 16 and just starting out in ‘N Sync, she was 23 and one-third of the pop trio, Wild Orchid — talk about robbing the cradle!

“It was before he got real heavy with Britney,” she told Australia’s Courier Mail.

The songstress is now happily married to Josh Duhamel and mom to baby boy Axl.

Britney Spears: 1999 – 2002

The Mickey Mouse Club. The matching denim outfit. Just freakin’ everything.

They grew up together on the Disney show, and began a romance in 1999.

It all came crashing down in 2002 after Brit allegedly cheated on him, which inspired his hit song “Cry Me a River” off his debut album, Justified.

“I just don’t think we were normal; there was nothing normal about our existence,” he told Vanity Fair in 2011.

“We spent way too much time being the biggest thing for teenyboppers.”

Jenna Dewan: 2002

There were rumors that Jenna, a backup dancer for ‘N Sync at the time (see video above), may have had a role in Justin’s breakup with Britney!

Now she’s married to Channing Tatum (talk about a sweet consolation prize), and mom to daughter Everly.

Alyssa Milano: 2002

JT was on full rebound mode when he started seeing the actress.

“Yeah, that’s true,” she admitted when asked about the “Mirrors” crooner.

“That was right after Britney broke his heart, I swooped in for the kill!”

She was 29 at the time, and he was 21. Cougar alert!

Cameron Diaz: 2003 – 2006

If an award for friendliest exes ever existed, it would easily go to Cam and Justin.

Despite their relationship not working out, the duo remain close pals — and even went on to star in two films together!

“I’m still friends with my ex-boyfriends,” she recently shared.

“I feel like all my relationships are strong — friends, family. I’ve invested in my people and they’re invested in me.”

Scarlett Johansson: 2007

She starred as his love interest in his racy music video for “What Goes Around… Comes Around” in 2007.

Then he was spotted visiting her apartment in 2011 (during his brief split from Jessica Biel — more on that later).

But did they actually date?

That’s something only the two of them know since they’ve never publicly discussed it!

Jessica Biel: 2007 – FOREEVVERR

Justin on Make A Gif

Ah, the gal who made an honest man out of our beloved JT.

Before they made it official, they broke up for a few months in 2011.

During that time, he was linked to Scarlett, Olivia Munn, Mila Kunis, Olivia Wilde, Ashley Olsen…but who’s counting.

In December 2011, Justin popped down on one knee and asked Jessica for her hand in marriage.

On Sept. 19, 2012, they made it official in Italy.

“I answer to a higher power now,” he joked about marriage.

“We have a couple of rules in our relationship. The first rule is that I make her feel like she’s getting everything.

“The second rule is that I actually do let her have her way in everything. And, so far, it’s working.”