Radar: Taylor Swift lost her virginity to Jake Gyllenhaal, he left her ‘damaged’

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This is the weirdest story. I actually had a moment of “should we even discuss this?” because it is quite intimately about Taylor Swift’s virginity. But my thought is: Swifty sings blind-item songs about her love life and heartbreaks and which guy screwed around and which guy betrayed her, and we already know some of this stuff anyway. So, fair game? Radar’s story is basically “Taylor Swift lost her virginity to Jake Gyllenhaal and the whole situation left her devastated.” Which I don’t even think is true. Swifty dated John Mayer before Jake and I always thought that Mayer was probably the one to… you know. Get there first.

Taylor Swift was heartbroken after she gave her virginity to Jake Gyllenhaal and he bailed on her 21st birthday party, leaving the singer locked in a bathroom crying the entire night, RadarOnline.com is exclusively reporting. According to an insider Swift, now 24, had been “saving herself for marriage” but was so smitten with Gyllenhaal, 33, that after three months of dating he convinced her to go all the way.

“She thought she was going to marry Jake, that’s how in love she was with him,” the source told Radar. “She was on birth control and he always wore a condom, taking no chances.”

But shortly after the two began sleeping together, Swift threw a 21st birthday party for herself in Dec. 2010 at her family’s estate in Nashville, Tenn. and Gyllenhaal was expected to fly in for the bash the source claims — but he was a no-show, leaving the “Our Song” singer devastated.

“The day before — all was set — he was coming, no issues. But the day of, she doesn’t hear from him at all. No texts, no calls,” the insider revealed. “Taylor thought maybe he was planning some sort of surprise. Nope. He didn’t show up and she locked herself in the bathroom and cried the entire night.”

And as Swift is known to do, the country starlet penned nearly an entire album about her heartbreak over Gyllenhaal.

“Her breakup with Jake inspired every word of RED,” the source told Radar. “The song that specifically references this ‘event’ is ‘The Moment I Knew.’ They lyrics are all about her birthday party and Jake not showing up.”

Some of the lyrics for the song include, “You should’ve been there, Should’ve burst through the door,” with Swift going on to sing, “You said you’d be here.”

Throughout the song Swift describes how she was waiting in her “party dress” for him to show up and admits that when he didn’t she retreated to the bathroom.

“What do you say, When tears are streaming down your face, In front of everyone you know?” the lyrics read.

The source tells Radar that Swift is still “stuck” on Gyllenhaal and says the relationship left her “damaged goods.” Reps for Swift didn’t respond with comment to Radar at the time of publication.

[From Radar]

The use of “damaged goods” is so dated and misogynistic. That’s what women were told in the 1950s, for God’s sake. “No man respects damaged goods, never put out before marriage!” As for this particular Swifty story… as I said, I personally believe that John Mayer was her first and I would be willing to believe that Mayer messed her up pretty badly (he’s such a toolbox). But I don’t doubt that Jake Gyllenhaal also messed with her head. I wouldn’t be surprised if Jake tapped out on events that were important to Swifty. But let’s also remember… they were together for what? Two months total? I’m not saying she didn’t have her heart broken. I’m just saying that she got years’ worth of song material from those two months of douchery. Swifty should just chalk that up to a win overall.

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Photos courtesy of WENN.

 

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141 Responses to “Radar: Taylor Swift lost her virginity to Jake Gyllenhaal, he left her ‘damaged’”

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  1. Badirene says:

    I thought Taylor and Toothy only went out a few times? Coffee, apple picking and the unicorn rodeo,no? Weird story and weird timing all round.

  2. Kiddo says:

    I don’t believe this story for a multitude of reasons.

  3. Original Tessa says:

    All of her songs to John Mayer had heavier implications of taking her virginity. John Mayer got there first.

  4. Nikki says:

    I wonder why her camp keeps putting out these stories. This obsession with her being the “good girl/victim”.

    I don’t think Jake’s people had anything to do with this. He’s back with Alyssa so if he wanted to “maintain the hetero image” I think they’d push that angle.

  5. Lark says:

    Ugh, Radar is crossing the line. Then again it’s Radar, the same place that was fooled by the ridiculous Britney & her former brother in law story and regularly run fake as hell stories. As gross and sexist as this story is, I guess I’ll “cross the line” too and say what I think: I totally think Mayer screwed her over badly. As far as Jake, I believe they dated far longer than the public knew about it…I mean, you don’t spend Thanksgiving half way across the country with a boyfriend of only three months imo. However, I honestly believe she’s over all of them at this point. I think she realized her dating life was becoming a punch line (which is kind of sexist in a way) and decided to stay single for a while.

    • Azurea says:

      Sure you could spend Tgiving across the country with a 3-month boyfriend, especially if you’re a jetsetting celebrity.

      Regardless of whether or not the story is made up, this girl is such a narciccist. Her songs lyrics are the stuff of immature diary entries which most people would be embarrassed to expose.

      • TG says:

        Agree and if every guy you go out with does you wrong or that is your perception then I wonder what it says about you. Taylor should figure out why she is always the victim. I don’t know how anyone stands her music. If I hear that cotton candy voice on the radio I turn it off.

      • HQ says:

        “Her songs lyrics are the stuff of immature diary entries which most people would be embarrassed to expose.” sounding like someone whose only heard her single, not her albums.

      • Mitch Buchanan Rocks! says:

        And they play this high pitched wailing crap while you’re trying to shop for groceries lol. I’ve taken to wearing industrial hearing protection while shopping and don’t care how it looks – at least I can concentrate and not have that whinging making the adrenaline go crazy.

  6. Jen34 says:

    Discussing who ‘took’ someone’s virginity is creepy. Even Taylor Swift deserves some privacy. However, you are correct that it yielded a high return.

  7. JaDeRu says:

    My eye is so side-eyed on this one that it has met the other eye around the other side of my head.
    That doesn’t even make sense. I’m gonna go drink more coffee.

    Ahem…The Gyll’s PR shenanigans.

  8. Aura says:

    Do we really need to know about their contraception choices?!
    Also, and I’m not saying I believe this story, but if it is true, standing up someone for their 21st with no explanation is a pretty shit thing to do

  9. cleveland girl says:

    I have no idea if this is true or not, but the album “Red” is a true masterpiece. Just listen to it from beginning to end. True piece of work.

  10. Samantha25 says:

    This story doesn’t make sense. They broke up 4 or 5 months after they went public. Besides it’s a lot more likely that Taylor Latner or John Mayer was her first. Or some unknown guy she was seeing between her celebrity relationships. I’m not sure why this is news. Do people really care now? Maybe it would have mattered just when they broke up.

  11. Miffy says:

    So he took her virginity and they know what kind of contraception they used… I’m amazed they didn’t elaborate on what position was employed and what music was playing in the background (hers, obviously). Congrats on the restraint, Radar. I’m getting a migraine from all the eye-rolling.

  12. Miffy says:

    And Kaiser: Totally agree, the ‘damaged goods’ line made me bristle.
    Heaven forbid that a girl not end up forever and ever and ever with the person who took her V-card! Didn’t we all just sleep with one person and stay with them forever? Thank goodness! It would be a shame if we were all ‘damaged goods’…. *grinds teeth and snarls at Radar*

    • Leila in wunderland says:

      Agreed. It has a lot to do with the idea that a female’s worth, value, and even respectability are tied to her overall ‘sexual purity’- or lack thereof. Unfortunately this belief about us has led to all kinds of problems for women and girls for thousands of years. You can see this thinking expressed all over the celebrity gossip blog world, and not just there. I don’t think people are fully aware of how anti-woman that attitude is or how much oppression of and violence against our sex that idea has been responsible for. That’s why people have no problem spewing it- they think it’s harmless. But then when they see examples of the results of that mentality- either in tragic news events, in their own personal lives, or in the stories of others, they’re saddened by it but they miss the connection. It doesn’t occur to people that in order for these problems in society to either stop happening or happen less often, the messed up belief system behind it needs to be taken down. Everyone has to be accountable. And aware.

      • Miffy says:

        All excellent points, Leila. However, I beg to differ that it’s not just a female based problem. Young women are told to hold tight to their virginity because it attributes to some kind of value or purity, but young men aren’t told the same, so in essence, by omission, their sexuality has no merit and doesn’t matter at all. It’s two extremes and destructive all round.

        There was a scandal here in Ireland last summer, ‘Slaine Girl’. A teenage girl was filmed at Slaine music festival performing oral sex on a random guy in the audience in front of everybody and of course it hit Youtube and Facebook, etc, etc and caused uproar in the media because of the ‘youth of today’.

        However, there was a seriously insightful blog written (wish I had the link, might post it later if I can find it) that summed up the mutual sexism of the whole thing, something to the effect of ‘She lost her sexual worth, he never had any to begin with’.

        The whole attitude is archaic and something that I will be addressing with my children (one boy and one unknown on the way) when they’re of age, your sexuality and your sex life are to be respected, but they’re not currency and they don’t affect your value.

      • Leila in wunderland says:

        @Miffy: Good points. A lot of that probably has to do with how men and women have been viewed. Men (with the exception of slavery) have always been viewed fully as people. Women have for a long time been viewed as property. There have been times when a girl or woman would be ostracized, beaten, sold as a prostitute, raped, or put to death for losing her virginity before marriage- or if people thought she had had premarital sex- because by doing this, she had lost or lessened her value. A man wouldn’t marry her, and her father could no longer profit off her through having his virgin daughter married off. Men wanted a virgin bride, and since women had so little power of their own their value really was tied up to how valuable they were to a man. Whether or not a female was valuable at all had a lot to do with whether or not she had been penetrated by a man- or whether or not people thought she was the sort of girl to allow a man to penetrate her while she was unmarried. That’s one of the reasons why the whole damaged goods/’ make sure you’re not seen as easy so that you can be respected’ is so disgusting and anti-feminist.

        Congratulations, by the way! :) You sound like you’ll be a great parent. The world needs more parents like you.

      • Miffy says:

        Leila, I read that comment this morning and my hormones caught me off guard. It’s taken all day but I’ve composed myself! Thanks :)

    • hmm says:

      Maybe damaged goods was referring to the psychological damage/mental state/man issues it left her with as opposed to the loss of virginity? That was my first reaction when I heard it, but who knows!

  13. Eleonor says:

    I don’t like discussing with whom she may have or have not lost her virginity; it’s something so private I think it shouldn’t even be on magazines, end of story.

  14. kibbles says:

    I find John Mayer to be so unattractive. I don’t understand why so many celebrity women are willing to give him their heart, even their virginity. Yuck. At least Jake Gyllenhaal is hot and has a nice body. Jake is probably the best looking guy Swift has ever dated. I like that she even though she has a somewhat pure image, she never came out as a virgin waiting until marriage like Britney Spears and Jessica Simpson when they were teen pop stars. I remember reading Swift stating in an interview that she wouldn’t discuss that subject. I think it is perfectly fine to have a good girl image and have a sex life.

    • Leila in wunderland says:

      I do too. But I also think it’s important for her and others who want a more traditional image for themselves to make sure that they don’t come off as promoting the idea that having that image intrinsically makes them better than females who disagree or who choose the opposite. Especially since they’re public figures. Ariana Grande and Adele are both good examples of this. They’ve chosen their images for themselves, but you won’t find them shaming other females who choose differently in order to make themselves look superior. (as a matter of fact, they’ve even defended other women in this area) That takes class, maturity, and open-mindedness.

    • Emily says:

      Agreed. I’ve always respected her for not discussing her sex life in interviews.

      Maybe she’s still a virgin, or maybe she has a secret sex dungeon with a constant stream of male escorts on speed dial. At this point it’s really none of our business.

  15. E says:

    I was thinking Joe Jonas, but then I remembered the rings and the 30 second break up phone call. Ouch :/

  16. Bb says:

    Look how young Will & Kate looked! Wow. Time flies.

  17. Ary says:

    I feel like she’s the dupeé instead of the dumper most of the time.

  18. CeCe says:

    ..”locked herself in the bathroom”… ouch. I’m sure that is one of the reasons Jake didn’t show…too much DRAMA. Sounds like more of a tantrum…host your party like a big girl, THEN cry all night…
    I’ve been there…thrown myself a party but make it all about the guy I was dating…embarrassing.

  19. The Original Mia says:

    Pretty sure Mayer got there first.

    OT: OMG! Kim looks so different now. Jeez. Step away from the plastic surgery table.

  20. The Original G says:

    Probably BS. Definitely TMI.

  21. Tig says:

    I read the “damaged goods” comment to mean that she was badly hurt and took a long time to bounce back- not that since she’s no longer a virgin, she’s “damaged goods”.

    I don’t buy the story, either. And seriously, who really needs to know?

    • Original Tessa says:

      Me too. I read it to mean that she’s never been the same since, in her mind, not in some guys mind. It’s her head that’s damaged, and her heart, not her image to other men. We all have had that relationship that jades us and makes us less trusting. Or at least I did, and almost ten years later I’m still dealing with it. I expect the other shoe to drop now, whereas before I was endlessly trusting and optimistic.

      • Tara says:

        Yeah, I’ve been there too. Seven years into a good relationship, and I still keep a half eye open. However, I definitely have more of a comfort level than in the introductory phases of a relationship. Wishing you further healing and good times ahead.

      • Lauraq says:

        So much! I was with my ex for five years, and he cheated on me for the entire time. I trust my current boyfriend, but I still can’t help but think sometimes…’(Ex) lied to me so convincingly. How do I know (boyfriend) isn’t doing the same?’
        Fortunately my current boyfriend knows the story behind my ex and takes care to show me his honesty, and be patient with me when I’m paranoid.

  22. kellyinseattle says:

    And all this time I thought she was still a virgin:) But, for the love of God, pls change up your lipstick sometimes…she’s very attractive but reminds me of a mannequin.

  23. sapphoandgrits says:

    I think JG’s camp put this very, very toolish story out. No way would Swift or any of her people do it.

    I have always thought JG is a tool, and if I thought he was straight, I’d totally believe he’d do something like this. I still think it’s possible, although I think John Mayer was her first, and agree with Kaiser that he messed her up really badly.

    I think it’s interesting that except for Mayer, Swift has mainly dated guys who are almost positively closeted. I still think it’s both funny and sad Joe Jonas broke up with Taylor to date someone even more closeted than he is.

    Anyway, this story is just creepy, and shame on whomever got paid for selling it to ROL.

  24. theoscandal says:

    i thought joe jonas took the price…and john mayer took the, uh, other prize…

  25. Bernice says:

    I wonder if a lot of Swiftys relationships aren’t predominately in her mind? Like she goes out with these guys but then does a lot of “what if” thinking and mines that for her songs. She is only 24 so we have lots and lots more years to put up with her guy done me wrong songs……. If I were a hetero male with a reasonable image I wouldn’t get within a mile of Swifty, much less actually go out with her. She seems like she beards a lot though and then uses her imagination to turn the bearded relationship into a “he left and shattered my world” song. Ugh ugh ugh

  26. booboolarue says:

    Am I the only one that is hating on her new hairstyle?

  27. IceQueen says:

    Way too private and detailed information. For this reason among other reasons I don’t believe this story at all… lol

  28. Jackson says:

    Look how different KK looks now vs on that old cover. Not like this is breaking news, but wow. Just wow.

  29. Nerd Alert says:

    Jeebus. It’s been three years since ANY of this happened right? There is a world of difference between 21 and 24; so much happens emotionally and developmentally during that time. I think it’s time everybody got over it. I’m assuming it was JG’s camp that sent this story in, because it really makes Taylor look like a tool if she can’t get over this by now.

    • SPEAK NOW says:

      Personally, I doubt Jake nor Taylor’s PR team sent this in. Its seems to be a slow news week and everyone loves a good, tragic break-up story. Especially when it comes to Taylor Swift, the “break-up queen”. (*rolls my eyes*)
      People just want dirt. That’s all this is.

  30. Twez says:

    There is no way that Mayer didn’t tap that ass.

  31. bettyrose says:

    Ugh I can’t with this story. These aren’t high schoolers and it’s not the 1950s.

  32. idk says:

    These two men should be disgusted with themselves for dating such a young girl…19 at the time. These men are in their 30′s. That’s gross. Taylor should stick to men closer to her own age as well. But Harry was a year or two younger than her and that didn’t work out well. Ok she should just enjoy being single for a while.

  33. P.J. says:

    Yeah well, according to Blind Gossip (which has a tendency to always be spot on-just check out their older blinds), Joe Jonas would SERIOUSLY beg to differ.

    Anyway, who knows what’s really the truth here but then again, why is this even a headline at all?? Obviously it’s Swifty’s camp who leaked this which is pretty gross. I mean, I don’t even want to think about having lost my own virginity! 😄 Eek.

    P.S. Doesn’t Taylor look absolutely GORGEOUS in that entire black sweater/skirt combo?? As a D-cup gal (who never ever shows cleavage), I’m always on the hunt for cute, figure flatteting, non-dowdy, modest outfit inspiration-not at all easy-and I think this look might actually fit the bill ☺ Love it!

  34. Xantha says:

    I think Radar made it all up.

    1) Radar has a history of being full of shit.
    and mostly
    2) Neither Taylor nor Jake will confirm or deny this officially. It’s too personal so they can get away with printing this story knowing there will be no retribution from either camp.

    And honestly, I don’t think Jake’s gay. That whole Toothy Tile became ridiculous after a while. It read too much like fanfiction to be true for me.

  35. Kelly says:

    Yuck. Also, she’s goddamn stupid as fck for dating all these douchebags, no pity here.

    • redlipstick says:

      She didn’t necessarily know that all these guys were douchebags until she dated them. Often times, people can be charming the first couple of weeks you know them and when you get close or serious with them, they show their ugly side. (But by that point, you’re already in love and committed.)

  36. CC says:

    I only remember their coffee dates, and seeing that I believe that Jake picked her as his beard Whether she knew about it or not is another story-After all Kirsten Dunst, as rumors go, supposedly started the boozing after finding him in bed with his boyfriend.

    IF he slept with her (a big big if), I’m sure it was for the same reason.

  37. qtpi says:

    Meh. We’ve all got our sad stories of guys treating us badly.

    One boyfriend I had during college (he was older, and out of college) broke up with me the weekend before finals started. Also the week of my birthday. I’m so wayyyyy better off without him but was hardcore crushed for at least a month.

  38. Irishserra says:

    Meh, this whole story just reminds me of how young and naive she really was and still is to a large degree.

    And I absolutely agree about the “damaged goods” label. It’s awful.

  39. LilyT says:

    Regardless of her love life revelations in songs, I think it’s pretty awful to write about when and to whom she lost her virginity to. Yes, times have changed and the idea a woman is “damaged” if she puts out is ludicrous. But, still, for many women virginity is a big deal.. And often a painful subject.

  40. GirlyGirl says:

    Damaged like he’s a “big” man? or damaged emotionally?

    or the more likely “fake damage to sell another crap-tastic album”?

  41. Lisa says:

    Since we are analyzing Taylor Swift songs, I’m going to say she lost her virginity way before John Mayer or Jake Gyllenhaal.

    From her 2006 song “Tim McGraw”:
    “Just a boy in a Chevy truck
    That had a tendency of gettin’ stuck
    On back roads at night”

    She probably lost her virginity in high school to someone who wasn’t famous, like Britney Spears did.

  42. Baskingshark says:

    Hm. When I read the headline “Taylor Swift Lost Her Virginity to Jake Gyllenhaal and He Left Her Damaged” I thought this was going to be a story about how a certain part of Jake’s anatomy is enormous…

  43. SPEAK NOW says:

    Okay, this article was clearly BS. I doubt either Jake or Taylor started it…it was probably some lousy editor with no new stories and spun a story off a Taylor song (The Moment I Knew), knowing how everyone loves to criticize her.

    And, seriously, why does everyone like to criticize her? It truly baffles me. She’s a truly gifted songwriter, talented vocalist, and hard-working individual.
    I can just hear the groans begin — but hear me out.

    Taylor is the youngest songwriter ever to be hired at Sony/ATV music publishing house (age 14). There’s a reason for that — she has a gift of using words with simple elegance and grace, managing to sum up emotions in a simple phrase or two. That’s exceptionally hard and, personally, I don’t think any writer could get enough credit for that. As she’s grown, so has her talent. Her lyrics — though didn’t seem deep and complex at first — are actually very, very well-written. Red, her most recent album, is a masterpiece of lyrics. (Some of my favorite off the album: “You call me up again just to break me like a promise, so casually cruel in the name of being honest.” ; “And all we are is skin and bone trained to get along; forever going with the flow.” ; “You wear your best apology, but I was there to watch you leave.”) Don’t dismiss her songs or writing skills based off her released singles, like “We Are Never Ever Getting Back Together” or “22.” Those are fun and cute but, though well-written, are no masterpieces.

    Speaking of not basing your opinion of her based on her singles — many people believe she always plays the “victim.” It’s true — she does sometimes. But not nearly as much as people are convinced. Many of her singles are the only “victim” songs off her album (not always, but often.) Whether she does that on purpose or its just a coincidence doesn’t matter, because in the end, they’ll still be top-charter songs. People like to listen to “victim” songs — a lot more than anyone cares to admit. Its okay to have a “pity-party” every once in awhile, as long as you pick yourself back up. Taylor picks herself up by writings songs about it.

    Who cares if all the songs she ends up releasing are about love? She writes to help her heal or think clearly or she writes about what inspires her, what makes her feel. Besides, most artists have love as their muse. Listen to the radio — there’ll be songs about love. Look at art — there’ll be pictures and paintings portraying love. Look at poetry — there’ll be poem about love. So why judge Taylor for writing about her experiences in love? Because she trashes the exes? Well only in some songs. And, anyway, so do many other artists. Look at Adele. Or P!nk. Or Eminem.

    Not only is Taylor already talented — she’s also ALWAYS looking for ways to improve. Needs improvements on her live singing (Yes, despite what many people believe she almost always sings live)? She takes vocal lessons. Needs improvement dancing (yeah, that girl can’t dance)? She takes dance classes. Needs some growth in her writing? She works with new writers to learn new tricks, tips, and advice.

    In conclusion, if you actually pay attention to Taylor (her lyrics, her album, her vocals, her artistry) and not silly articles and headlines like the one above, you’ll find a respectable, lovable artist who only wants to make people happy via her music.

    • LadySlippers says:

      @Speak Now: My daughter has used more than one Taylor song to get through something that’s difficult in her life. She’s a budding writer and really enjoys that part of Taylor’s music.

      No idea whether or not either camp put it out but wouldn’t put it past an editor facing a slow week either.

  44. lady_luck says:

    I believe this story. It would seem that the specific facts match the lyrics. Somebody from the party spilled the beans. You know, both guys are douches, it’s unfortunate, but I can see why she was “damaged” after them because she was young, vulnerable, naive and unprepared. She probably had a rosy concept of love and romance and unicorns and rainbows prior to these letches. It’s making her a strong, independent woman any ways, which is always a good thing.