1. Kirsten Dunst and Jake Gyllenhaal
Do yourself a favor and fall into a Google image k-hole with photos of Kiki and Jake. The couple dated for two years before finally splitting in 2004 and let’s face it, they both have downgraded since. Jake has resorted to patrolling local high schools for future girlfriends (Taylor Swift) and Kirsten has endured one particularly stormy relationship with alcohol. Why can’t they just find their way back to each other again and skip away to a patch of indie sunflowers together? OMG, I bet their convos used to be so cute. “Babe, have the last sip of my aloe vera water.” “No babe, that aloe vera water is all you. Kill it!” It’s hard to say why they ever broke up but we can only speculate. I’ve tried calling Kirsten for comment but she blocked my number and threw her shoes at me when I tried to approach her at Westway. WTVR, diva.
2. Mischa Barton and Meth
Mischa’s been looking a lot better these days but is it weird that I kind of miss it when she used to look like this? Those were the daze, weren’t they Misch? Full disclosure: My friend used to work at a fancy spa in L.A. and had access to all of these celebrities’ phone numbers, so I made her give me Mischa Barton’s number so I could do some prank calls. The first time I did it, she actually picked up (um, who picks up numbers they don’t know, desperado?!) and I started screaming, “Oh my god, Mischa. It’s Cara and Danielle! We’re outside your house and ready 2 rage!!! Come outside, you slut!” Mischa was like, “What?” and then pretended to be someone else, which was fruitless because, hello, you can spot that faux-British accent from a mile away. Anyway, she never picked up my phone calls again and I was depressed for, like, a week after.
3. Gwyneth Paltrow and Brad Pitt
I mean, can you believe these two ever dated? They were the ultimate ’90s dream couple! They also looked like identical twins, which was creepy but kind of hot in its own way. It’s a bummer they had to break up because now they’re both stuck with people they clearly traded down for. Even though Angelina Jolie is gorgeous, she has Pitt and their 20 adopted orphans by the balls in a chateau somewhere. Meanwhile, Gwyneth is married to the # 1 snoozefest, Chris Martin, who probably weeps in her arms every night before bed. Ugh, no thanks. Brad and Gwyneth need to have a rende-screw ASAP.
4. Johnny Depp and Winona Ryder
The two misunderstood goths of Hollywood would date. Of course. It’s too perfect! A publicist’s nocturnal emission! But these two actually seemed to be totally madly in love with each other. Johnny Depp even tattooed “Winona Forever” on his body (which he later changed to “Wino Forever”, natch) and they used to make out all kinds in public. I’m not sure why they eventually split but I bet it was when the coke and Ecstasy ran out and Johnny just looked at Winona and was like, “Oh, You’re crazy. Oops!”
5. Britney Spears and Justin Timberlake
This couple was the teen dream. They were everyone’s idol, the true personification of young love! And you could just tell these two were in disgusting teen love with each other. The kind of love where if you don’t hear from each other for ten minutes, you’re like, “Beb. Where are you beb? I feel really distant from you right now. Did something happen? Did you fall out of love with me when you went to Walgreen’s to pick up your prescription? ANSWER ME!” Yeah, they were definitely in that kind of love. They even wore gross matching denim outfits to award shows! Their break up was devastating. Ordinarily, when you get your heart broken for the first time, you try to soil their name at your high school, but because Justin and Britney were superstars, they took their revenge to the Billboard charts (he with “Cry Me A River” and she with “Everytime”). God, being famous must be really weird sometimes. Remember the alleged dance-off Britney and Justin had after they broke up? Obsessed. Anyway, they need to get back together. Justin will CPR Britney back to life and Britney will save him from Mary Camden. Win/win!