Jessica Simpson kissed Justin Timberlake in 2006 & he was a douche about it

Jessica Simpson shares poses with the cameras as she arrives at Jimmy Kimmel Live

A large chunk of the advanced promotion for Jessica Simpson’s memoir was the story of how she stopped drinking and stopped taking pills. Jessica has been clean and sober now for more than two years. In those two years of sobriety, I guess I haven’t been paying much attention to her TV interviews? I was actually sort of shocked when I sat down to watch Jessica’s interview on Jimmy Kimmel Live. Even two years sober, Jessica still sound like she’s drunk as hell. It’s just the way she speaks, and I also think she’s getting lip injections, which affect the way she enunciates too. But lordy, she absolutely sounds hammered here. Also: she tells about ten bonkers stories.

The Chuck Norris School of Acting… wow. But there’s also this horrendous story about the time Jessica kissed Justin Timberlake and he was just as skeevy as you could imagine:

On Wednesday, Jessica Simpson walked Jimmy Kimmel through her new memoir Open Book on Jimmy Kimmel Live, where she revealed that ex Nick Lachey wasn’t the only famous boybander she’s kissed. While reminiscing about her failed Mickey Mouse Club audition in the ’90s and recruiting Chuck Norris to help improve her acting skills, the “With You” singer shared that she had a brief fling with Justin Timberlake after she and the 98 Degrees frontman divorced in 2006.

“After divorce and he was out of a relationship, he was, like, over at my house, we shared a nostalgic kiss, but I thought, ‘Oh, this is interesting,’” she recalled. “And he took his phone out and started typing. And I was like, ‘Okay, I hope that’s not, like, another girl. Like, did I, like, stick my tongue out too much or, you know?’”

Just wait, the story gets even better. “But apparently him and Ryan Gosling had a bet on who would kiss me first when they were 12-years-old,” she continued. “And so, he texted Ryan and said he won the bet. And I was like, ‘Oh, okay. Um…So we don’t kiss again. That’s done.’”

But, if 12-year-old Simpson had her way, she would have chosen the La La Land actor instead. “Ryan was the one that I was, like…when I was 12, I was, like, ‘This guy is so cool and he’s from Canada,” she dished. “I don’t know where that is on the map, but I really think that that’s amazing.’ And there was something so cute about him. But Justin won the bet.”

[From E! News]

I mean, “boys will be boys” and I’m not going to get indignant about two twelve year old boys making a bet about who would kiss the pretty blonde girl first. But the fact that Justin held on to that sh-t into adulthood and that he TEXTED RYAN after he kissed Jessica? That’s appalling. The Chuck Norris School of Acting is appalling too, but for different reasons.

Also appalling? Jessica literally wore this TO Jimmy Kimmel’s studio. Like, this is her everyday outfit and she changed for the show. LMAO. Jessica is so much fun.

Jessica Simpson shares poses with the cameras as she arrives at Jimmy Kimmel Live

Photos courtesy of Backgrid.

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54 Responses to “Jessica Simpson kissed Justin Timberlake in 2006 & he was a douche about it”

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  1. Flamingo says:

    I think the consensus is that Justin Timberlake is a dbag. I’ve never read a story about him that made me think, “yeah, this guy is likable.”

    • Jegede says:

      I didn’t even realise JT and Ryan knew each other that well.

      I mean I know they were all on MMCH but a friendship after that?

    • holly hobby says:

      They were in new Mickey Mouse club together. He is just gross. Can’t he wait til he goes home to text his bro?

  2. Lady Baden-Baden says:

    Yessss! Was hoping you’d cover this one! LOVE a story where JT is once again revealed to be a total bellend!

    • CherHorowitz says:

      Not related to he story but just here to appreciate that you used bellend to describe him. One of my faves!

  3. LORENA says:

    i hope not but she really does sound drunk, she did on her Hoda interview as well

    Maybe it is just how she talks

    • Lori says:

      Thats kinda mean spirited.

      • LORENA says:

        No, not what i meant. Just saying her accent and the way she talks could be the reason she sounds drunk

      • Meg says:

        But this post makes the same point, Jess sounds drunk. I hope she didn’t fall off the wagon because yes she sounds not sober. It’s easy to think celebs feel comfortable with attention but many stress out, get nervous and alcohol helps you let go of your inhibitions. I don’t think it’s a coincidence that industry has such a high number of addicts, recovering addicts etc.

    • stormsmama says:

      She seems high on coke to me – :(
      I hope she is just jittery with nerves…?

    • Lady Baden-Baden says:

      I don’t think she sounded drunk. I think she sounded nervous. LOTS of nervous laughter. Great stories but not a very comfortable watch (even though I have a soft spot for her)

      • Mel M says:

        Yeah if you’ve watched all of newlyweds you know this is just kind of how she is. She doesn’t seem drunk or on pills to me but it does seem like her lip filler are getting in her way.

    • Laura says:

      Personally, I think she’s just been messing with her face so much that it has altered how she talks. It looks like her face is too tight to really enunciate the words properly and even smile normally. I know that sounds mean but I’ve been a fan of hers since way back & her face doesn’t move naturally.

      • Maggie says:

        I have aunts with too much filler and Southern accents that sound just like that. I can’t explain it, it’s just a thing.

  4. MellyMel says:

    JT continues to be a trash human!

  5. Naddie says:

    Not surprised. I read horrendous stories about him and Britney, he being the horrendous part.

  6. LidiaJara says:

    Her boot line is one of a few that comes in my size (12) and every time I think “those are cute!” and then see the name I feel bad about myself.

    • Spicecake38 says:

      Haha I come across some of her shoes/boots/bags at TJMaxx sometimes,and I (kind of) like them.About 10-12 years ago I had like 2 of her bags and sold them at a yard sale… a twelve year old bought them.😅

  7. Emily says:

    Ryan Gosling probably never replied because he’s better than JT and has grown up. I hope.

    • Kate says:

      Haha I was picturing him looking at his phone like “cool story bro” and putting it back in his pocket.

      • Emily says:

        Ryan probably doesn’t even have JT’s number in his phone and replied “who is this? Sorry new phone.”

    • LadyLaw says:

      I’m sure it eats Justin up inside that Ryan is considered a legitimate actor and he is not.

  8. stormsmama says:

    JT is a douche and water is wet!

  9. Spicecake38 says:

    She couldn’t find Canada on a map…?

    • Slowsnow says:

      She is doing the I am so dumb shtick that brought her fame and tons of money. Also, she was 12. Some of my kids are geography savvy and some aren’t.

      • Spicecake38 says:

        I hope it’s just her shtick.
        This just cracks me up because I still remember the pageant girl who,when asked why so many Americans couldn’t find?somewhere? on a map she answered that it was due to a shortage of maps…Favorite you tube watch ever!

      • Mumbles says:

        Yeah I wish she would just stop that. Goldie Hawn started out as a “ditz” and then dropped the act a few years into her career. Jessica should follow suit.

        We all know that JT is an absolute dbag. Makes you wonder about his celebrity buddies. Fallon is so enamoured of him he had JT as a musical guest for an entire week.

      • Slowsnow says:

        I dunno. I am one of those intellectuals who knows everything about everything (or so my kids see me) and then I had kids and had to review my stance about the difference between intelligences. Some people are bad at knowing random stuff without experiencing them and she comes across as someone who is not gifted with info but who is actually quite clever. Her substance abuse is probably related with that and my take (totally imagined) is that she may have taken some prescription drug for her appearance on this kind of shows where people have to be wittiy, quick and funny. Super stressful for people who, like her, are a bit dreamy and not hung up on that kind of smarts.
        She seems to have been ‘coached’ to stick to her routine when she actually looks like someone who wants to talk about her struggles…
        For some reason I feel really defensive of her.

      • Spicecake38 says:

        Yeah, I don’t think she’s a stupid person didn’t mean anything bad about her just,sometimes she comes off dingy and she can’t be that bad,I mean she’s still relevant after two decades so she’s got something,and for the record I really like her too,regardless of her intellect,either way.

      • Veronica S. says:

        Mumbles – Just from people who were moderately “famous” in my field (not even close to RL celebrity, so you know – worse because the stakes are so low lol), my experience is that the narcissistic ones can be shockingly good at building up the egos of those who fawn all over them (i.e. Fallon with Timberlake) while treating everyone else like garbage. They can switch the charisma on and off very quickly, so it wouldn’t shock me if his industry friends weren’t all total bastards because he knows how to treat certain people right to get what he wants.

        Now, how they overlook how they treat other people outside their circle is another story.

  10. Slowsnow says:

    That was uncomfortable. She was clearly talking about the stories that Kimmel’s show told her to talk about and seemed utterly bored to be ‘performing’ them.
    That said, she is incredibly endearing ans smart.

  11. Prairiegirl says:

    My reaction to this headline: “Of course he was.”

  12. stormsmama says:

    I can’t help but love her tho!

  13. lucy2 says:

    One kiss that ended badly is considered a “fling”? Huh.

    As for JT, everyone knows he’s a douche, and yet he so often proves it, again and again. I wish I could be surprised he was that petty and childish, but no.

  14. Pamspam says:

    Douches gonna douche.

  15. ME says:

    Was Jessica famous when Justin and Ryan were 12 years old? I thought Jessica became famous in 1999 when she released her first album…she was 16 or 17. She wasn’t on the Mickey Mouse Club so how did they know who she was at that age?

  16. Andrew’s Nemesis says:

    JT – the acme of asshatism

  17. Lucy says:

    Basically, Ryan was the one who did some growing up.

  18. Pulplove says:

    Justin Ti me me me berlake never disappoints. Every story about him makes my disdain for him grow more profound. Here’s to stability.

  19. Jegede says:

    I wonder, did Simpson talk about her fling with Dicaprio?😏

  20. Grant says:

    I love her. I can’t help it and I don’t totally understand why…? Maybe because she was so huge in the aughts when I was in high school/college. I remember so many of my straight bro friends had that poster of her Rolling Stone cover where she’s Swiffer wet-jetting in stiletto pumps plastered on their dorm walls…

  21. Nancypants says:

    Bless her heart.
    She’s never been eloquent but I’ve always had a soft spot for her.
    She’s been wildly successful and has worked a lot to line the pockets of other people just like Britney and I don’t believe it’s her accent. It might be how she speaks or lip injections and she sometimes talks with her hand over her lips, so, I’m hoping for the best.

    That being said, this morning I heard a radio show host talking about a time when she worked with, “Danny Bonadouchebag” – her words, not mine – and he threw back 5 shots of tequila right before going on a talk show and bragging about his sobriety.

    BTW, that snake outfit…I want to shake Jess out of it and then take the outfit out back and take it out of my misery. Anything that slithers, is up to no good.
    Did you hear that PETA wants to replace Punxsutawney Phil with a robot critter? Yeah.

  22. Kathgal says:

    She doesn’t seem drunk to me, it is almost like she just came from the dentist and is still frozen or something. I don’t remember her talking this way.

  23. Lucian Gold says:

    I actually know a girl who trained under Chuck Norris. Not his acting school but his fighting school. She has gone on to be a world class instructor. Maybe he should stick to one genre.

  24. Ninjacat says:

    She Is fun! I have always really liked her!

  25. What. . .now? says:

    JT — Forever Douche. He is such a gigantic asshat, I wish someone would bring him down a peg or 20.

  26. Mar says:

    One thing is for sure, her style absolutely sucks. I could make her look so much better if she let me dress her and do her hair and makeup because she’s really gorgeous.

  27. jules says:

    Lainey did the math on this and it sounds like JT was in a relationship with Cameron Diaz at this time. So he looks like a double-douche. Make it a triple with what he just did publicly to Biel.

  28. Nibbi says:

    I always thought she seemed like a basically kind-hearted person, but I think the whole “dumb blonde girl” trope is and always has been so damaging. She seemed sincerely not to know what “chicken of the sea” is or “buffalo wings” were at the time, and I could see how that was funny to everyone… but as something that increased her popularity and likeability like that? Sometimes it did seem like she played it up… like she was quite comfortable in her “dumb cute girl” role. Perhaps that wasn’t her fault, as growing up she probably had that positively reinforced by the people around her, and as developing her brain never seemed to be anyone’s priority… I dunno. I just have mixed feelings on the whole thing. Holding a chick up on a pedestal because she’s dumb and sexy – it was like the dumbness was supposed to increase her sex appeal, and I suppose it did- just doesn’t seem like a positive thing for society, or young girls, or men’s view of women, or something. I’m not saying she should have been banished or something, but perhaps that whole ditzy thing being encouraged and celebrated, the whole dumb blonde cliché being played on & reinforced, wasn’t the best, although it increased her celebrity. She’s clearly not mentally handicapped or anything; it didn’t have to be that way.

  29. MrsPanda says:

    Ewww another gross story about JT. I heard an awful one that after hooking up with Britney that first night, he boasted to a bodyguard and said ”Dude, ‘smell my fingers’, I just hooked up with her. So gross I can barely type it. But it’s a similar story, bragging about his conquests in a vulgar disrespectful way. I know most young guys talk s*** to their friends, but he seems exactly the same way 20 years later!