Taylor Swift Lost Virginity to Which Famous Ex (Who Dumped Her Via Text)?!

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Taylor Swift was reportedly heartbroken after giving up her virginity to one of her famous exes, only to be crushed when the guy bailed on her birthday part.

The loss of Swift's v-card, followed by that rejection, left the unlucky-in-love singer locked in a bathroom crying the entire night, according to Radar.

So who was the celebrity who convinced her to go all the way?

Taylor Swift Curves

According to a supposed insider ... it was Jake Gyllenhaal!

Swift had been “saving herself for marriage” but was so smitten with the movie star that after three months of dating, they consummated the relationship.

“She thought she was going to marry Jake, that’s how in love she was with him,” the source says of the relationship, which fizzled out in late 2010.

Now 24, Taylor threw a 21st birthday party for herself in December 2010 at her family’s estate in Nashville, Tenn., and Jake was expected to fly in for it.

He no-showed.

“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 phone 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.”

Eventually, he did text ... to break it off.

Talk about pulling a page out of the Joe Jonas Breakup Playbook, only even less cool than leaving a voicemail. Naturally, Swift was crushed by Gyllenhaal.

“Her [split with Jake] inspired every word of RED,” the source said of her album. “The song that specifically references this ‘event’ is ‘The Moment I Knew.’

"The lyrics are all about her birthday party and Jake not showing up. 'You should’ve been there, Should’ve burst through the door. 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.

Moreover, years later, insiders say that the popular country-pop singer is still "stuck" Gyllenhaal and says the relationship left her “damaged goods.” Poor girl.

As for other famous guys who dated Taylor Swift for various lengths of time and with varying degrees of seriousness, scroll through the (long!) gallery below:


No it's just rumors because I read Justin lost his virginity too someone else .anyway Taylor swift is amazing and talented she deserves better Jake is a douchbag slimball his movies ain't that good and he ain't that good of a actor I hope he finds a woman hurts and used him like he does to wemen I believe in karma.


I believe. John Mayer got her first...read the words to Dear John...Poor Jake...must he be punished for that mistake he made in even being seen with her.? Neither guy stayed as liong as they did for the coffee dates? Taylor was too immature for him.

@ Regina

Bryan call taylor swift


Wow....that sux if it's true...I don't care for her to much and I love him....guess I'm switching...I waited til I was 19 before I gave up the V card.. I was with him over a yr before anything happened...we were together 7 years had a son and...we've split up in 94 and are still friends..just went to his wedding..that's respect...what Jake did was awful...I got lucky..


She shouldn't have gave up the panties so quickly. That's what's wrong with women. They give it all away and when they get married they have nothing to give their husbands. Glad I waited until marriage. It's so much better to be "untouched" and your husband to know he was your "first".

@ Elaina

Also, how is dating and waiting 3 months too quickly?

@ Elaina

Way to be judgmental and you sound like a doormat.


I doubt it is true. If it is, it's his loss. She's beautiful, talented, and worth a quarter of a billion dollars.


I'm a little jealous.I lost my virginity in the 80's to a guy with spiked hair and an earring,while lying on his trench coat.Losing it to Jake sounds nice.I bet they even did it in a bed.


stop giving it away!!! It's precious for god sake & you guys are giving away free to every Tom dick and Harry . Is anything sacred any more . Serves you right then if you going to go into the bed with everyone what the hell is to be respected certainly not the opening her legs everywhere you deserve what you get


To give up your virginity is giving up your innocence. When a girl decides this is the one that I will blossom into a woman with she must love this man awesome . For jake to be so heartless as to go thru that knowing how she feels about him then on top of it rub salt in wound by not showing up on her birthday in front of everyone . You are a piece of shit jake , someone needs to knock you around alittle put some sense in that pea brain of yours you stupid moron . Boycott all future movies he's not worth it . He ain't that great of an actor to begin with .

@ Annie

Boycott his movies because he "wronged" Taylor Swift?You will have to boycott a lot of movies,music,tv shows,etc. with all the guys that have "wronged" her.If her first relationship worked out and she lived happily ever after,she wouldn't have a career.

@ poisonapple

Taylor swift call Bryan


WHAT A SCUMBAG!!! Us women should just boycott every man for doing shit like this thinking we don't have feelings and to do it on her birthday what a low life. I curse and wish what he has done to every girl that was low down I put it on him so when he finds the love of his life that she screws him good let him cry in the bathroom all night ASSHOLE


This makes Jake a real DB, don't care how big a star he is. I don't think he anything to look at but I'm not Taylor or waiting on him for my 21st birthday. This is beyond rude and hurtful and I'm not a Suft fan. I think she needs to stop writing these songs if she ever hopes to have a BF.

@ Spare+Me+

Taylor swift love Bryan

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Taylor Swift Biography

Taylor Swift and Friend
Taylor Swift is the next big thing in country music. She hails from Pennsylvania and has a younger brother named Austin. Personally,... More »
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Taylor Swift

Taylor Swift Quotes

I think it's kind of fun to call out your ex-boyfriends. Like why do this if you're not gonna take the opportunity to always have the last word. It's so much fun.

Taylor Swift

I saw that documentary on Britney Spears, and I feel bad for her—she can't leave her house!

Taylor Swift