Two Guys, A Girl and A Pizza Place - 1998-2001
Editorial use only. No book cover usage. Mandatory Credit: Photo by George Lange/20th Century Fox Tv/In Front Prods/Kobal/Shutterstock (5876450b) Ryan Reynolds, Traylor Howard, Nathan Fillion, Suzanne Cryer, Richard Ruccolo Two Guys, A Girl and A Pizza Place - 1998-2001 20th Century Fox TV/In Front Productions USA Television
That is a whole lot of brown, Ryan. Seriously, look at this young whippersnapper. Entertainment Weekly seized upon him early and kept trying to make Ryan Reynolds a huge thing, and he wasn't UNFAMOUS at all, but I would sometimes think, "Chill OUT, EW, I think he might have peaked." But then I believe it was The Proposal that hit big, and suddenly, EW was right.
Ryan with Tara Reid
These two look awfully businesslike for a pair promoting a movie that, internationally anyway, was known as VAN WILDER: PARTY LIAISON.
2003, with Alanis
And here we go: Ryan and Alanis started dating in 2002, and this was February 2003. I will say this: They do a lot of happy gazing at one another.
May 2003
He appears to have matched his tie to her silky dress, which is a solid gesture. She may be wearing the exact same pair of boots as she was in the previous shot. Alanis was the more famous of the two at this point, but she seems so chill and just content to be there, and not at all interested in making anything about her.
May 2003
MORE gazing. Alanis seems like a good egg. Honestly, when you compare this with how VERY little we got of Ryan and ScarJo, and the small amount we get of him with Blake -- and she always seems more comfortable in that limelight than he does -- it makes me wonder if every celeb has that first relationship in the spotlight where it all seems so great, and you want to share it and you don't care who knows, and then the relationship ends and you feel so burned by it all that your guard goes up against letting the media too far into your next ones.
June 2004
See? They're schmoopy.
June 2004
They got engaged at some point this year. Her dress looks deeply improvised and he looks dashing in the oxblood leather.
December 2004
Ryan may be wondering if Alanis adapted her costume from some old Ren Faire robes they had in the back of their coat closet.
But, he's good with it anyway. This is the last event at which I have pics of them together. They broke up in 2007, I think, so that's a long dry spell, but they were both busy and maybe by this point he was already getting gun-shy about how much people knew of his life. (She might have been, too, but as a VERY bracingly, blazingly honest songwriter, she seems less apt to avoid getting personal.) It's always a little bittersweet to look back and see two goopy kids in love and know it didn't work out, but at least they both seem to have landed in solid places with enduring, solid partners. As Alanis said herself, you live, you learn.