The Ladies of Justin Timberlake: A History of Questionable Dating Choices

When I walk on by, girls be lookin' like, "Damn, he fly." 

At this point, Justin Timberlake is certifiably B.A. This much we know. The guy has parlayed his breezy charm and multiple talents into a career that's been going strong for about two decades now. He's won six Grammys and four Emmys, sold more than 66 million albums worldwide (with an assist from his old N*Sync comrades), and has a total 10-year box office haul of $812 million from his film appearances. Just for reference, "serious actress" Kate Bosworth has a 10-year total of $483 million.
Justin also helms his own record label, runs a successful clothing line, and owns two restaurants. He's shown a knack for bouncing back from potentially career-ending scandals (remember that little Super Bowl incident with Janet Jackson?). Recently, music legend Elton John personally suggested that JT be the one to play him in an upcoming biopic. Oh yeah, Justin also made this happen ... 
Basically, this dude gets up in the morning and pisses excellence. You can't stop him. Nobody can. So, it seems somewhat strange that his cumulative dating history plays like a continuous reel of "seemed like a good idea at the time." Let's take a look, shall we? 
(Note: We're only going to go with confirmed celebrity galpals and one major cheating scandal. We're not going to bother with the rest of the bang rumors ... or I'd be writing a legitimate novel. I have a real job, you know.)
1. Fergie (aka Stacy Ferguson), 1996

The "how" of it: Fergie went all pedobear on Justin, logging a failed fling when she was 23 and he was (wait for it ... wait for it ... and ...) 16. Don't judge her too harshly, though. She was probably on meth at the time.
Why this was a bad idea: The age difference between a 23-year-old and a 16-year-old is a much longer bridge than the difference between a 33-year-old and a 26-year-old, no? It's pretty obvious that she shouldn't have went there. Plus, she was addicted to METH for f%ck sake! It doesn't venture much further into "bad idea" territory than that. Oh, she makes sh!tty music, too. 
2. Britney Spears, 1999-2002

The "how" of it: Britney and Justin were the original Selena Gomez/Justin Bieber brand of pop power couple ... meaning that since I was a teenager at the time, I thought this was an awesome pairing, but everyone I knew who was over the age of 22 totally didn't get it. And rightfully so ... We'll always have those matching denim outfits, though. Why this was a bad idea: Britney allegedly cheated on Justin, causing him to go all bat-sh!t crazy. However, unlike Taylor Swift, his revenge song (and corresponding video) was actually pretty cool. Plus, Britney later showed the world what bat-sh!t crazy could REALLY look like ... c'mon, you remember. Justin had some 'splaining to do ... even though he had broken up with her years prior. Oh, she makes sh!tty music, too. 
3. Jenna Dewan, 2002

The "how" of it: Jenna was a back-up dancer for Justin when he ventured out on his own as a solo artist, and eventually, the two were doing the no-pants dance together ... or so the grocery store magazines said. Why this was a bad idea: Jenna is now married to Channing Tatum (pictured above). Would you honestly feel good about yourself if someone you dated ended up married to Channing Tatum? Nah, didn't think so. 
4. Alyssa Milano, 2002

The "how" of it: Justin was briefly linked to Alyssa after the thing with Jenna died down. I'm sure it seemed like a major win for Justin. With Alyssa, JT got a hot older chick who loves animals and baseball. Score!Why this was a bad idea: Who HASN'T this chick been linked to? Her black book probably reads like the white pages for the Los Angeles area. Plus, she's a die-hard Dodger fan ... who is pictured above wearing a Yankees shirt. I don't care if you were dating a Yankee at the time (she probably was) ... loyalty much, Alyssa? Shame on you. 
5. Cameron Diaz, 2003-2006

The "how" of it: It appeared that Justin was fully committed to the cougar thing when he started dating Cameron. The two enjoyed several years of hard-bodied sun and surf together before eventually parting ways ... only to reunite onscreen for 2010's Bad Teacher. Wow, I wonder if that was awkward at all. Why this was a bad idea: Just speaking from personal experience, but I don't know one straight man who refers to Cameron Diaz as anything but "f%cking annoying" ... and I'm inclined to agree. Also, I'm pretty sure that she's addicted to meth also. Don't ask me why. I'm just pretty sure.
6. Jessica Biel, on-and-off from 2007-Present

The "how" of it: Back in 2007, a funny thing happened. Ryan Reynolds was rumored to be dating Jessica Biel. Justin Timberlake was rumored to be dating Scarlett Johansson. The guys then pulled the ol' switcharoo: JT took up with Jess, while Ryan rode the marriage/divorce train with Scarlett. Despite her abysmal taste in pantsuits (pictured), Justin and Jessica have been hooked up when it's convenient for Justin ever since. Why this was/is/will always be a bad idea: Jessica Biel, while the object of a great many male fantasies, is a DUMB b!tch! She can't act worth a damn, but allegedly thinks she's on-par with Anne Hathaway as a contemporary. She said she "respected" strippers after playing one in a movie. (FAIL!) Justin can basically do whatever he wants, whenever he wants, and to whomever he wants, and she will take him back. Apparently, she's just THAT spineless. Speaking of which ... 
7. Olivia Munn, (allegedly) 2010

The "how" of it: Justin allegedly carried on a "steamy three-day affair" with Olivia after the two met at a press event for The Social Network. Shortly after, reports surfaced that he although he was still dating Jessica and her terrible clothing, he was continuing to reach out to Olivia ... even though she and Jessie B. are basically the same person. Why trade?  Why this was a bad idea: Look, I just plain don't condone cheating, even on someone as stupid as Jessica Biel. Plus, this chick is also fairly moronic herself. Yeah, yeah ... I know I just opened myself for all sorts of nerd wrath because all the Attack of the Show! dorks are in love with her, but I really do not care. I thumbed through a copy of her book, Suck It, Wonder Woman! in Barnes & Noble once. I'm pretty sure my IQ dropped 10 points as a result. That's why I can't do math. Damn you, Olivia Munn!

So, Justin, since you can't seem to pick a good one for yourself, allow us to suggest one for you. Here you go, so make it happen, dude. Believe me, the people WANT this. LeBron James takes our advice. You should, too. 

You can't say you don't think this is a stellar notion. Mila Kunis is sexy ... and you know it!

Sources: People.com, The Huffington Post, Wikipedia, various source links scattered throughout

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