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Lily Allen's New Boyfriend is Almost 20-years Her Senior!

| Filed under: AnglophiliaLily AllenLove Line


British songstress Lily Allen spent the fist day of 2009 frolicking with her new silver-haired boyfriend off the coast of St. Barth on a luxury yacht.

According to reports, 23-year old Lil's new guy is a 45-year old English art gallery owner named Jay Jopling, who also happens to be friends with the singer's dad.

Kinda creepy!

Would U date one of your parents' friends?

Up until September, Jopling was married to a big artsy photographer named Sam Taylor-Wood (Sam also happens to be 'best friends' with Sir Elton John). The two were once dubbed the art world's 'golden couple'.

In a past interview Lily said, "I think I like much older men. I hang out with much older people, I go for dinners at posh places and talk about art. I’m meeting more interesting people who tax my brain."

It looks like Jay is exactly what Lily was looking for!

[Image via Fame Pictures.]

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86 comments to “Lily Allen's New Boyfriend is Almost 20-years Her Senior!”

  1. 1


  2. 2


  3. 3

    Perfect white trash!

  4. 4

    Lol, I like this pic!

  5. 5

    Who the hell cares?????

  6. 6

    Sorta looks like he's saying to her "Get the fuck off me you crazy little girl!"

  7. 7

    Perez Hates Me °°

  8. 8

    my bf is 45 and i am 26. BFD!!

  9. 9

    She's LAME!!!!

  10. 10

    Maybe he can give her some fatherly advice and make sure she doesn't screw up anymore.

  11. 11

    I wish I knew myself as well as I do now when I was her age. I love older men, just didn't know it when I was 23. Would have saved a lot of time.

  12. 12

    its official…shes a cunt

  13. 13

    eh Perez, do the math: 45 - 23 = 22 years her senior. And almost double her age. But he looks cute

  14. 14

    lololololol who even cares about this girl? i havent heard any music from her in 2 years.

  15. Uker says – reply to this



  16. 16

    get over it, they are both adults

  17. 17

    perez your such a judgemental bully

  18. 18

    By the way Perez - Lily is 23, her bf is 45, that is MORE than 20 years older, not "almost" 20 years older.
    As I said earlier, for having the easiest job on Earth, you really suck at it. Between the grammar mistakes (for a college grad, seriously?) and the tons of other errors, like this one, to the completely false items you report as being absolutely true - you really should take some English/journalism classes or something.

  19. 19

    Re: automat table cleaner – She just released a single. You are stupid.

  20. 20

    Re: automat table cleaner – listen to the radio, dildo.

  21. 21

    It doesn't look like he is all that into her. Just sayin.

  22. 22

    I heard she was actually friends with the couple about a year ago, when they said the guy took her under his wings lol, how she limes or hangs out with older folks and talks about art! Well it seems that's not all they were doing lol

  23. 23

    Those of you that obviously hate Perez, why do you bother coming to this website? If he is so awful then why waste your time?

  24. 24

    What brain??

  25. 25

    compared to you pig face boy,
    nothing is "creepy", you disgust us, you jealous, crude, false, weak, talentless sychophantic pustule. good on them if they are happy

  26. 26

    Re: Sleepwalker – hahaha it does

  27. 27

    What's creepy about it? She's over 21. So he's a family friend, so what? I love older men, they are more experienced and know more than the little snot nosed 20 and 30-somethings. My bf is 13 years older than I am and the best lover I have ever had.

  28. 28

    Seeing her tits was disappointing, why buy the cow when the milk's for free? -10 on the fuck-o-meter.

  29. 29

    She's smart to go for older men,23 is not a child.

  30. 30

    lily likes saggy wrinkly balls

  31. 31

    This little trog does need some height and stabilitly in her life.
    But she wouldn't know art if Rodin's "The Thinker" fell on her head.
    Silly, silly trog.

  32. VGirl says – reply to this


    Maybe that's what she needs…although the fact that he is daddy's friend it is kinda creepy…but hey if it makes u happy

  33. 33

    Re: jonalisa – i do listen to the radio, but over where i live in america, we just dont care about the ugly english and their jacked up teeth.


  34. 34

    They look cute together.

  35. 35

    I so glad she found her a nice artsy photographer, art-worldly, friend of Sir Elton John to hook up with. She's only one more step closer to maybe finding a straight guy to hook up with.

  36. May says – reply to this


    I don't see a problem with the age difference.

    I see a problem in that he is so totally NOT interested.

  37. 37

    I'm a geezer at 47. My brother is 41. Just ended a relationship with an 18 year old drop out from Jr. college. At first, to a man, of course it sounds delicious. Like eating a real fresh piece of fruit or opening a Xmas present everyday. But evidently she couldn't handle him asking her to "help around the house"…and she dusted him saying that "he was starting to act like my mother"….jeeez what do you expect. I know when I was 18, I just wanted to drink, screw and repeat that…

  38. 38

    Do you have the right to call anyone else's relationship creepy?

  39. 39

    Re: Sleepwalker – Exactly what I was thinking

  40. 40

    come on perez she is the 2008`s biggest train reck do you really expect anything more from her ?

  41. 41

    Re: automat table cleaner – you sound so ignorant im suprised you can even read

  42. 42

    Hot Hot Hot Hot Hot Hot!

    Dating older men has a lot of pros (cons too but who cares)

    1. Financially stable… no Apple Bee's dinners.
    2. Mostly drama free, once they've past 40 they just wanna have fun.
    3. They already know the ins and outs of treating a woman right, granted they've been around 20+ years more than the person they're dating.
    4. MIND BLOWING SEX. again… it's about knowing the in's and out's

    Bottom line is, if you know yourself well enough at 23 to know what you like, then damnit, go for it. you're damnned if you do dammned if you don't.

    Congrat's Lili! I'd love a silver fox!

  43. 43


  44. 44

    Perez, he's not "almost" 20 years her senior. He's 22 years her senior. Besides, this is likely a photo-op. This female is one of those people who get attention from the media for sleeping around, getting drunk and fighting. she's not famous for anything since no one can name any of her songs. Maybe if the media stop giving her attention, she'll go away.

  45. 45

    Hell Ya!!!
    Stop judging!
    He is sexy.
    I am 28 and my partner is 43. He'll be 44 in March. He is sexy and sweet and the best relationship I've ever had. You go Lily!

  46. 46

    Re: idaknow – You're a loser and likely a gold digger. You little girls disgust me.

  47. 47

    So this is what she found out to make people talk about her this week ?
    She has a crap album to promote and for someone we havn't heard of in a while she's been everywhere with her antics lately…HOw strange….NOT !
    Lily Allen is a "daughter of" celebrity and her record company (with whom she got a recording contract via family connexions) made up the whole myspace thing up because they feared that she would have got no credibility at all and would be seen as just another Kelly Osbourne. I can testify that because i used to work on the "project".
    Her lashing out at other celebrities in the press are perfectly thought and scripted to give her headlines and make her look like an edgy loud mouth.
    As a person she's awful, a real spoilt brat and what she says in her interviews is the opposite of how she behaves….she claims being insecure when she's full of her herself and really mean spirited.
    Iif i wanted to say something she would herself say to give you an example of how horrible she really is i'd say that she's such an horrible person that even her unborn child prefered killing itself before being born to her…You thin t's mean ? Well that's exactly the kind of thing she would say about others.

  48. 48

    OMG! Why is Lily so desperate? She has the worst taste in men….yuck. I hope she doesn't get herself knocked up again the first month she is dating him..

  49. 49

    Why not dude, shes happy! and older men are HOTT! youre just jelous Perez!

  50. 50

    Not as creepy as you wanting to fuck little Zak Efron

  51. 51

  52. 52

    Re: awsomekrys – TWAT

  53. 53

    If Demi Moore can hook up and marry Ashton Kutcher with about the same amount of years between them..Then why can't Lily Allen hook up with an older man? In these days it's so common for either sex to hook up with someone way older or younger. Psh..it's not even that big of a deal. As long as she's happy..then who cares?

  54. VGirl says – reply to this


    Re: holly18 – true

  55. 55

    looks like she's hugging her grandpa. ewwww

  56. 56

    That doesn't look like an embrace; it looks like she's stumbling drunk and trying to stand up and he looks disgusted. As for "taxing her brain" sheesh, the Teletubbies could do that!

  57. Alexx says – reply to this


    age to me does not matter!
    i am 15 and am engaged to a 19 year & i am the happiest i have EVER been!

    and if lily is happy then let her be:)


  58. 58

    Lily looks really thin!

  59. 59

    fix your title. homeboy IS twenty years her senior. (or more accurately, 22)

  60. 60

    actually he is 22 years her senior.

  61. 61

    isn't it kind of like monica on friends? I forgot the guys name but she dated her dad's friend. It didn't seem that weird on the show.

  62. 62

    Of course Lily Allen needs an older more mature brain to fill the space where she has none! Last week it was pictures with her tats out on a beach at Christmas time…oh so 'Amy Winehouse' this week its pictures in the arms of an older man with friends on a boat….oh so 'Sienna' so trashy cos shes been 'liking' her dad's older friends for years. Dont get me started on her behaviour on Jools Hollands BBC show on NYE….the words, cracked out, Judy Garland's last days will do to describe the performance!..sad, so very sad.

  63. 63

    Bruce Willis is 53 and his girlfriend is 30. Why can't Lily date someone that much older? I wouldn't want to but to each their own. Looking forward to her next album. Comes out next week I think, doesn't it? And I wouldn't necessarily describe her as a trainwreck like a previous poster did. That label would be reserved for the Britney Spears/Amy Winehouses.

  64. moon says – reply to this



  65. 65

    Ha! They should hang with the Piv and his little much younger Chickie!

  66. kitt says – reply to this


    so what yes he's old enough to be her dad but hes not and it's not like he's 98! and she looks happy for once which is good let her alone her life people can tell you 'he'll break your heart' or 'he's to old' or shes too young for you etc but they have to learn that themselves so why be mean bout it? she is nearly 24yrs has money and wants fun…its not like hugh hefner old enough to be those 19yr old twins great great grandad ewwwwwwwwwwwww

  67. 67

    Re: get up – you are so right. i too have had the 'pleasure' of working with silly allen and she is a vile nasty little beeyatch. shes a spoilt little brat who loves to mouth off about whoever she wants, thinking its her godgiven right and we all want to hear what she has to say, but when the shoe is on the other foot and someone starts giving her shit, she gets all upset and starts blogging telling everyone that the media is sooo mean to her, in order to get all these fucking lemmings who think she's cool to leave messages telling her how much they love her to boost her sad little ego. she talks to people like they are beneath her, ive seen her scream and shout at her supposed best friend and assistant (who just took it like a muppet). shes vile. give me cracked up amy any day. at least she has a talent somewhere beneath the mess. lily is just a little media whore. and as for the excitement about her album?! this would be the album that her record company are putting out as a last resort cos they've asked her to re-record it twice because its been so shit. and how funny that lily choses to cavort with her new man friend weeks before her new single is out. shes making mugs of you all…… enjoy!

  68. 68

    oh - and one more thing ass kissing americans - she cancelled her last US tour cos she couldnt be bothered. thats how highly she thinks of you guys.

  69. 69

    Lily looks beautiful, she has lost so much weight. You don't choose who you are attracted to, at least he's rich and not using her! Or a drug addict that is gonna bring her down… Go Lily!

  70. 70

  71. Suze says – reply to this


    So? This is hardly a scandal.

  72. 72

    Re: love4chihuahuas – >>> Young Mans Slave - Older Mans Queen

  73. 73

    With so many immature men out there, I too prefer older men. Have fun, Lily!! I do wonder if that guy's still a friend of her dad's, though. Don't hit on your friends' daughters!!

  74. 74

    So when she was born, he was already in his 20's. Nice.

  75. 75

    Is that the only guy she can get?!

  76. 76

    Is he any relation to Janis Jopling? He kind of looks like her (lol)

  77. 77

    DANGG !
    LOL i guess he likes her men old

  78. 78

    Oh, shut the fuck up, Perez. Who cares how old her boyfriend is, or what the age difference is? Can't you just appreciate and celebrate love, intimacy, and connection, instead of getting all snarky about it?

  79. 79

    she look like a little kid ewwwww

  80. 80


  81. 81


  82. 82

    23 is hardly too young. Good for her! Better than some fucktard drug addicted rocker. An elegant, smart and obviously handsome older man? Hmmm… jealous much??? And aren't YOU a little too old to be hanging out with 21 year olds and partying with them, but you do anyways… just sayin'

  83. 83

    Gross….not the age difference..Lily Allen. *Puke*

  84. 84

    Re: londonting. – We think the same of her too. She's disgusting like all of you brits.

  85. 85

    Re: _Insert_Catchy_Name_Here_ – hey rather be a disgusting brit than a morbidly obese yank whos never left the town i was born in cos i don't own a passport.

  86. 86

    So what????
    I'm 23 and I dated a 41 year old once… older men are better. Guys at our age are horrible!
    I always date at least 4 years older