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You know and love Milo Ventimiglia as super dad Jack Pearson on the hit NBC series This Is Us. But, as season three of our favorite binge-cry show comes to a close and Jack recedes further into the past, we can’t help but feel a little separation anxiety coming on. So, in true This Is Us fashion, we’re taking it back to the early days of the 41-year-old actor’s career. Here, ten photos of peak vintage Ventimiglia that’ll tide you over until season four.

young shirtless milo ventimiglia
Barry King/Getty Images

1998: 21-Year-Old Milo Being Very Tongue in Cheek

We’re just gonna leave this here.

Milo Ventimiglia teen choice awards
Ron Galella/Getty Images

2000:23-Year-Old Milo Hitting the Teen Choice Awards

We bet there was a Good Charlotte album in his Discman at this time. 

Milo Ventimiglia ripped button down
Ron Davis/Getty Images

2002: 25-Year-Old Milo Rocking Business Casual

…With a ripped (?) button-down, no less. To be fair, this was taken in the early days of Gilmore Girls when he was a total bad boy.

Milo Ventimiglia shaggy hair
Mark Sullivan/Getty IMages

2004: 27-Year-Old Milo Perfecting His Smirk

This was around the time Jess asked Rory (Alexis Bledel) to run away with him. Milo, if you’re reading this, we would have.

Milo Ventimiglia Alexis Bledel together
Kevin Winter/Getty Images

2006: 29-Year-Old Milo Almost 30 Flirty & Thriving

I mean, the way Bledel is looking at him? Mood.

Milo Ventimiglia in glasses
Patrick McMullan/Getty Images

2009: 31-Year-Old Milo Doing His Best Clark Kent

This is what adulting Milo looks like, people. Take it all in.

Milo Ventimiglia in a hat
Jason LaVeris/Getty Images

2010: 32-Year-Old Milo Dabbling in Hipsterdom

Flannel? Check. Fedora? Check. Too cool for school pose? Check. 

Milo Ventimiglia with silver hair
Jason Merrit/Getty

2012: 34-Year-Old Milo Making His Silver Fox Debut

Pass the salt and pepper, please.

Milo Ventimiglia long hair
Jamie McCarthy/Getty Images

2014: 36-Year-Old Milo Going for the Lob

At the time, Ventimiglia and those gorgeous locks had just wrapped a stint on Mob City and the Crackle series, Chosen.

Milo Ventimiglia jean jacket
Amanda Edwards/Getty Images

2015: 37-Year-Old Milo On the Cusp of a Big Break

In 2015, he was starring on an ABC series called The Whispers when it was suddenly cancelled. Frustrated with acting, Ventimiglia considered leaving the business and going to work on a vineyard, when all of a sudden a little show titled This Is Us came calling.

All’s well that ends with Milo Ventimiglia as Jack Pearson. 

RELATED: ‘This Is Us’ Creator Jokes ‘Everyone Dies!’ in Season 3 Finale (and Gives Actual Spoilers)

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