Taylor Swift spent the weekend with Conor Kennedy at his Mass. prep school

Summer will officially be over in a matter of days. And will all of those sun-soaked summer romances be over as well when Cruel Autumn rears her dying head? Sorry, I didn’t mean to, like, write poetry about the seasons. My point was just that Taylor Swift and Conor Kennedy might not last now that they’re separated by distance, by work, by school, and by the seasons. But do not fret! Fair Swifty and her handsome heir are still making it work. In between whirlwind promotional duties and appearances on behalf of her new album, Swifty managed to stop by Conor Kennedy’s prep school, and they enjoyed a quiet weekend together. Because apparently that’s allowed at fancy prep schools?

As summer winds down, Taylor Swift’s work schedule is revving up. And while her new love Conor Kennedy has already gone back to school, the couple, whose romance heated up over the summer, did not stay apart for long.

On Saturday, Swift, 22, and Kennedy, 18, headed for the intimately lit Taylor’s Tavern & Restaurant in Greenfield, Mass., a quaint New England town only a few miles from Kennedy’s prep school in Deerfield.

“They were very happy and very polite,” says a source. “She was very sweet.”

The young duo, who have spent a lot of time together in the past few months, enjoyed a warm, sunny weekend in a scenic part of Massachusetts dotted with farm stands and country stores. Kennedy and Swift also indulged in a classic country pastime, antiquing.

Paying a visit to Deerfield’s Old Station Antiques on Saturday, they browsed together in the store not far from Kennedy’s dorm, according to a source.

On Sunday, Swift once again had to say goodbye. She left late in the afternoon – as Kennedy presumably prepared for Monday morning classes.

[From People]

If you haven’t guessed by now, I have no idea how the rich live. Everything I know about the children of the Rich and Famous, I learned from watching My Super Sweet Sixteen and the Mitt Romney campaign. So it seems a little bit bizarre to me that a student attending a fancy prep school is simply allowed to leave school for a weekend (?) to hang out with his pop star girlfriend. I mean, I guess they don’t have classes during the weekend, and I guess students are allowed to go home on weekends too. But are they allowed to just sign out and go to a bed & breakfast with their girlfriend? It feels like there should be more oversight, right? Can I get some more red tape and regulations at the fancy prep schools? This isn’t college! You can’t just do whatever you feel like.

Photos courtesy of WENN.

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102 Responses to “Taylor Swift spent the weekend with Conor Kennedy at his Mass. prep school”

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  1. Boring says:

    Sadie Hawkins is right around the corner!

    • muffin says:

      hahah!!! that’s funny

      and he is 18. legally an adult…don’t ask me why he’s a still a hs junior, but maybe that has something to do with it

      either that or taylor signed him out as his legal guardian since she IS 22 after all…

      • cw says:

        maybe he got held back bc he’s slow…..would make sense, bc i think she is slow as well, seriously

      • Kristen from MA says:

        If he’s actually ‘slow,’ that would show how entitled he is. Deerfield Academy is supposed to be an elite school – meaning the best students attend. In his case, it would be elite as in rich and well-connected.

      • Lucinda says:

        If he has a late summer birthday, his parents may have chosen to start him a year late. That is common, especially with boys as they tend to mature emotionally a little later than girls. I assume he will be a senior this year? My son’s best friend is in the same situation and he is anything but “slow”. Additionally, if he is 18, than he can legally sign himself out unless the prep school has a different agreement. In public school, 18 year olds are allowed to sign their own permission slips.

      • bfan says:

        It is a common practice among wealthy people that educate their children in fancy prep schools like Deerfield Academy. They hold the child back a year at the beginning of formal education and the child enters kindergarten at 6 years old. Sometimes they have them repeat 8th or 9th grade as well. It gives the child a tremendous learning advantage over kids that start at 5 years old. The end goal is to help them achieve better grades to assure they will attend the best universities. It’s also used for kids that are in athletic programs to give them the physical edge. The practice is known as “redshirting”.

    • Elizabeth says:

      @ Muffin
      The high school junior thing – does that means he’s in grade 11 right now? I’m a bit confused. I hate to think he has to deal with Taylor Swift’s crazy and grade 11 physics at the smae time.
      @ Erinn
      You’re right. He would go for antiguing if there was sex afterwards. He’s 18.

      • jules says:

        “I hate to think he has to deal with Taylor Swift’s crazy and grade 11 physics at the same time” is definitely the best thing I will read all day. I might as well go back to bed.

      • muffin says:

        @ elizabeth, Yes, 11th grade….

  2. Colu says:

    My first two thoughts:

    1) High school boys go antiquing?

    2) With so much time spent apart from her high school boy, a leaked nude photo scandal would not surprise me at all.

  3. Olivia says:

    At boarding school, as long as you get a day excuse from your house counselors, you can go wherever you want on the weekends.

    • Amelia says:

      Mm, I don’t know if it’s different in the States, but when I boarded, assuming we were in the Sixth Form (16-18) and had permission from our Housemaster and a guardian, we could take off for a weekend so long as we were back for Monday.

    • DaisieB says:

      Taylor is the best thing that could have happened to Conor. He returned to school as the guy who is in a relationship with a clean-cut superstar…. NOT the guy whose mother hung herself and whose father is a twice-divorced recovering addict from a family that is cursed. My brother graduated from Deerfield and I am very familiar with that part of Massachusetts. It is a tiny New England town full of historical homes that are museums, like Williamsburg and there is NOTHING but antique shops. Taylor does not drink alcohol.

      • Dallasman40 says:

        How do you know what these people do or not do? And how clean cut is she if she got banged by John Mayer?

    • Charmander says:

      It really depends on the school.

  4. KellyinSeattle says:

    1) Stay away from Conor
    2) change your lipstick
    2) change your hair….
    4) quit trying your “All American’ Imagine
    5) Put all knive down
    6) Stop trying to be Stepford Wife
    7) Get a personaility
    8) All of the above

  5. Brown says:

    This story gives me the heebie jeebies.

    What high school boy goes antiquing? If I had asked my high school sweetheart to go antiquing he would have 1. asked me wtf antiquing is and 2. laughed in my face.

    Wonder what she will be wearing to prom…?

  6. dorothy says:

    This whole thing has officially gone into creepy overdrive.

    • LeeLee says:

      That was my first thought too: really sad and creepy.
      I have nieces that age and I know I would find it bizarre if they were trolling the hs in their 20s. If Taylor was a guy people would be in an uproar.

      • EmmaStoneWannabe says:

        Of course..they dont want a gay Kennedy scandal on their hands ;)

      • OriginalTiffany says:

        I used to think that 20 year old guys that had a high school GF were creepy as hell.

        This is way over the creeper line. He’s a junior! I’d be so embarrassed to have a high school junior for my BF when I was 22!

        I was in bars having fun like normal college kids! My BF was a musician, so I hung out in more bars than I care to admit. He’s my husband after 23 years, so it worked out fine:)

    • Stubbylove says:

      That was my exact first thought – creepy.

  7. samira25 says:

    I don’t know anything about boarding schools but I have a hard time believing that students can’t leave campus at all. They probably have curfews and need permission from home to leave for the entire weekend. Taylor probably said I want to go antiquing and Conner is willing to do whatever his rich, famous girlfriend wants to do. He is only 18. I still find it creepy and embarrassing that Taylor is dating a high school student.

    • The Original Original says:

      When I was in high school my boyfriend went away to a boarding/prep school (in Massachusetts no less) and he was allowed to leave every weekend…as well as I was allowed to come visit any weekends that I wanted (but not to stay over in the dorm). It is completely creepy that she would date a high school boy, and I do mean boy.

      • Liberty says:

        Creepy + sad = disturbing

        And yeah, what’s that famous line? “the rich are different than you and I.” But, stilllllllllllll…….

  8. Quinn says:

    Lord…she tries to domesticate EVERY guy she dates. She’s the girl that carries around her wedding planner, even though she doesn’t have a boyfriend.

    • Hakura says:

      I totally agree. And I don’t think there’s too many things a girl could do to scare guys off so quickly as immediately bringing up commitment, how many kids do you want to have, when are we moving in together??

      If I guy treated me that way, he’d be *out* of there.

  9. Anastasia says:

    Oh my Lord, in that top picture, the profile one, she looks EXACTLY like the mannequins they have at the Salvation Army store! I’m not even trying to be snarky here, I wish I had a picture I could show y’all. She looks exactly like the mannequins!

  10. Imelda says:

    Someone please tell me that is her natural hair colour otherwise WHY would you do that to yourself?
    I thought ash blonde (if thats what it is) went out with the 70′s.

  11. Kat says:

    I went to boarding school in massachusetts and you definitely cannot just go off to some hotel with your girlfriend. When I wanted to leave I had to get permission from the dean of students, my parents, and the parents of the kids house I was going to. I wonder if Swift’s parents had to call in and vouch for her? hah!

    • Charmander says:

      Yeah, so did I. I think it depends on the school. Although I will say that this piece makes it seem like boarding school must be so relaxed and rule-free, when in fact it’s exactly the opposite. SUPER easy to get in trouble, and punishments are way harsher.

  12. Belle Epoch says:

    College age girl dating behind schedule junior in HS is SERIOUSLY CREEPY. I don’t blame him at all, particularly since his mother just hanged herself. But I find her behavior predatory and overwhelming. He should be at football practice making fart jokes with his buddies, not playing husband. EW.

    • Esmom says:

      “He should be at football practice making fart jokes with his buddies, not playing husband.”

      THIS. Why is his dad not intervening?

      • Pamspam says:

        His dad isn’t intervening because this takes the heat off of him for being a bastard (allegedly) to his ex wife and it leaves him the freedom to pursue his new relationship. He doesn’t come off as particularly parental, so I think this works for him.

      • Relli says:

        And also dating a celerity… Cheryl Hines, i cant believe it never been mentioned on this site.

        So i am guessing he doesn’t have much time for things like keeping tabs on his kid because there are a lot pap shots of the two of them and it doesn’t appear that his children are present.

    • grace says:

      “playing husband” – they just had a meal in a local diner! According to the Boston Herald, Taylor went antiquing alone but met up with Conor again the next day for lunch at a cafe.

  13. it'sjustblanche says:

    She doesn’t really bother me. Yes, it’s odd to date a high school boy at 22 (although Jerry Seinfeld was dating a 17 year old high school girl at like 40 and no one did more than blink) but whatever. He’s been through a lot and she seems very young.

    I can’t stand her music but at least she’s not acting like a skank. Plus, I love her clothes.

    • fabgrrl says:

      Are you serious? Jerry Seinfeld caught major flack, and rightly so, for that creepy romance.

    • grace says:

      This isn’t comparable at all to Seinfeld. The age difference isn’t creepy. Conor is old enough to serve in the army. So surely it follows that he can go on cutesy dates with a clean-cut popstar.

  14. T.C. says:

    Attending weddings, antiquing, sure those are things 18 year old boys are into. Not. Taylor Swift you are a 22 year old woman dating a high school boy. Have you no shame? Before anyone cries double-standard, I feel the same way about 22 Year old adult males dating high school girls. Creepy.

    • grace says:

      According to the Boston Herald, Conor wasn’t there when she went antiquing. And all his teenage relatives attended that family wedding so I don’t follow your point.

  15. GoodCapon says:

    I don’t know what it is with teen boys thinking it’s cool or hip that other people can see their boxers. No, it’s not cool nor it’s hip. It’s incredibly tacky.

    Conor, hike up those board shorts please.

  16. Soxfan says:

    Boarding school teacher here in CT. Yes, he could leave as long as he has his dad’s permission along with deans, dorm parent, advisor, etc. Our students may sign out on the weekends (most boarding schools do have classes on Saturday) after classes and take a taxi to places as long as they are in the boundaries (specific miles away). For an overnight, again parent’s permission, though I am not sure what rules do apply if the student is 18 and older?? Fun fact-one of the pics of Taylor frolicking this summer on the Cape with the Kennedy clan included one of our students!!

  17. cw says:

    is he really a junior in high school?

    I’m sorry i don’t care if 18 is the age a consent….if she was sleeping with him the summer after sophomore year, while she’s 22, then that is stat rape, or it should be
    this is just a gross story – if she were a 22 yr old guy scamming on a female sophomore, NO WAY any parent would stand for that

    • Marigold says:

      What grade someone is in has nothing to do with age of consent. I believe the age of consent is 16 in MA. Either way, he is now a legal adult. She’s a major creep for dating a high school student but he can sleep with her legally.

  18. menlisa says:

    This is beyond disgusting.

  19. SleepyJane says:

    Creepy McCreeperson.

    Is this even real? How do you date a guy in his 30s, and then follow that up with a high-schooler? Even if the Jake thing was fake, that was less creepy. She is a mess.

    • rumbleseat says:

      Well, simple. You go to the 30 year old man with a fantasy in your head that he will be your Knight in Shining Armor. Reality inevitably intrudes, and you realize that grown-ups just can’t or won’t fulfill your idiotic and developmentally arrested fantasies. So you then turn to the only available Kennedy in the targeted age group to see if he will be capable of fulfilling your dreams. Look on the bright side: Since he’s a Kennedy, he probably won’t have to try as hard as Jake would have since the name conjures up a lot of wish fulfillment in and of itself.

      • SleepyJane says:

        True. But, she is a grown-up. What you have described is arrested development, for sure. But, I’m not really buying what she’s selling. I don’t think she’s been that developmentally stunted. Something is off here, hence my disbelief in the reality of this situation. It is obvious that there is only one logical deduction left to be made; she is a robot.

  20. Kate says:

    I thought he was a high school senior (it’s perfectly normal to be an 18 year old high school senior, though normally it’s the kids who have birthdays after Jan. 1st; they turn 18 halfway through the school year). If he really is a junior, that just makes this extra creepy. I’m a little embarrassed for her. And yes, you can leave boarding school with the permission of your housemaster/house counselor and a guardian. Nothing unusual there.

  21. Jacquelantern says:

    I find it so strange she has dated someone as old as Jake Gyllenhaal (30) and someone as young as this kid. Just bizarre.

  22. pf says:

    Can someone explain to me where this story came from that he is a junior? I understand if he was a senior, that makes some sense, but an 18 year old junior? What? Did he repeat two grades? Start kindergarten late? Does Taylor realize she has to wait nearly two years until he’s done with school before she can marry him and live happily ever after?

    • Snow says:

      The Boston Chronicle reported that he was a junior in their coverage of crasher-gate and it’s been said that he missed a year of school due to bad allergies. HOWEVER, a previous cryptic poster on Celebitchy (who hinted that she knew something) basically said a few things; that he wasn’t held back due to allergies and point blank asked: don’t you find it a little funny that, with all their money, they didn’t decide to put Conor through summer school to make up his credits? She made a throwaway line about how his parents had a really hostile relationship…

      Take from that what you will. I certainly did. I got the impression that his parents held him back or neglected to enroll him due to some very real family relationship problems. Was Conor collateral damage?

      I don’t even know, but Kennedy gossip makes me feel all icky. So much darkness around that family. Can we go back to making jokes about Camelot, ponies and rainbows?

      • Tiny Dancer says:

        That was probably me. And no it’s not because his parents neglected to enroll him. Or because of his allergies. Or because his mom committed suicide.

        He was kicked out of his previous prep school due to behavioral issues and wound up transfering to Deerfield where he had to repeat 9th grade. (he went from one prep school to another, let’s establish this).

        There you go.

      • dreamer says:

        Prep school is a lot more fluid than traditional school–things operate a little differently there. For instance, you’re not a “freshman,” you’re a Third Form, Junior would be Fifth Form etc. A lot of people take post-graduate years after graduating (still not sure why, sometimes it’s sport or college thing, sometimes they just like prep school so much they stick around and delay college). Not unheard of to graduate at 20, 21, 22. And with enough money, the administration will accommodate just about anything! Surprises me even more that any prep school kicked out a Kennedy.

  23. Relli says:

    I didn’t go to boarding school but i went to super fancy private school and as long as your parents/family keep donating, you can do what you want! Rich people live by different standards :)

    Regarding his age and grade, i believe its been stated he started school late due to being a sickly child or perhaps he just started late. I know that one of the guys in my school days was a year older than the rest of us because he had grown up on the east coast and that particular community they started kindergarten at 6 not 5.

  24. NavyWife says:

    Until now I have always been ok with Taylor. Mostly because my seven year old daughter loves her music and there is no langauge or sexual references in it. Now though I’m thinking I might need to lock up my nine year old son because when Connor outgrows her during senior year she might start looking for my Jayden. He is a really cute little guy after all! This has defiantly turned into a ” Chester Chester the Child Molester” situation.

    Ugh I think I just vomited in my mouth a little!

  25. EscapedConvent says:

    OH MAH GAH! I’ve never seen anyone look so much like a mannequin. Look at the surface of the skin, & the hair! Are we sure that thing is human?

  26. Aria says:

    She looks like a doll, a creepy one.

  27. rumbleseat says:

    If you turn 23 the year your man turns 18, that is not a four year age difference. She was born in 1989, he in 1994. Let’s all stop helping her make this look (ever so slightly) less creepy than it is.

  28. Alexis says:


  29. Amy says:

    I’m not sure I understand this “scandal.” Many college freshman who are 18 date 22 year old seniors. I don’t know why the kid is still a junior (maybe he took time off from school after his mother’s suicide). Yes it’s a little weird he is still in high school but 18 is the age of a college freshman. And um, trust me that 18 year olds are no saints. I think the only reason people are up in arms about this is that technically Conor is still in high school.

    • Esmom says:

      Technically? He is actually in high school. And he just lost his mom to suicide. And his family life was notoriously troubled. And he’s a Kennedy.

      On the other hand, people are OK with Sam Taylor Wood and her husband’s age difference. Maybe Conor is an “old soul.” Somehow, though, I don’t think so.

    • grace says:

      I don’t get it either..

  30. Luxx says:

    “Everything I know about the children of the Rich and Famous, I learned from watching My Super Sweet Sixteen and the Mitt Romney campaign”


    &I instantly associate Swifty’s freakishly perfect squirrel face with “CREEPER” now. Sad.

  31. Kosmos says:

    Well, it’s certainly not the typical romance for many reasons, but if they’re happy for the time being, and the Kennedy family is happy, I see nothing wrong with them being together. If it doesn’t work out, I really hope Taylor doesn’t design another break up song. The age difference does seem peculiar, but if they have enough in common, I guess that’s all that matters.

    • lauren says:

      Taylor wants to be a Kennedy-she is trying to dress all cutesy and sweet..wearing her hair in a ponyta il–trying to look virginal and Ivy League. She has gone from boinking John Mayer when she was 19, to teenage Conor, when she is 22…this is bloody weird. My son is 19, and I would be freaked out if Taylor was flying in to see him on weekends–and he is in college!

    • lauren says:

      Taylor wants to be a Kennedy-she is trying to dress all cutesy and sweet..wearing her hair in a ponyta il–trying to look virginal and Ivy League. She has gone from boinking John Mayer when she was 19, to teenage Conor, when she is 22…this is bloody weird. My son is 19, and I would be freaked out if Taylor was flying in to see him on weekends–and he is in college! The Kennedys like to play football, tennis, go sailing. Taylor is acting bizarre and no one seems to care.

  32. Scarlett says:

    There is just something about this woman that I find incredibly creepy. I don’t know if it’s her Stepford Wife creepy lifesize doll looks or her clingy and controlling behavior. She seems so retro like she stepped out of the 50′s. Why would a 23 year old want to hang with a guy who has two more years of high school? Weird..even for Taylor Swift.

  33. Creampuffs&Peanutbrittle says:

    Holy cr@p! They went antiquing on Saturday? Wow. That sounds like loads of fun for an 18 yr old guy! Kennedys like to do physical stuff, maybe hiking or biking or something? Something interesting? She is such a loser! A cross between a little old lady and a 12 yr old. Poor Conor. Swift she is not!

  34. grace says:

    Yikes, a lot of angry comments! I think she seems genuinely sweet. The age difference isn’t big – a college freshman and senior.

  35. juju says:


  36. Carolyn says:

    Cue music for when the Breakup happens…”we had the most perfect summer when you were at School. Autumn came and you dumped me. You are such a fool. Crying on the doorstep begging you to stay (hey hey). Picnics and antiquing they were such fun. I really really thought you were The One. Now I’m all alone what am I to do (ooh ooh ooh) etc etc”.

  37. mln89 says:

    this is…just weird. when is she going to grow up?

  38. DB says:

    I can’t help it – she Stalker-Scares me

  39. Grace says:

    Ha! This is divine payback. The Kennedy’s have always abused their women. Taylor is going to get her way or Conor is going to come up missing. She has the look of murder-suicide to her.

    • tmbg says:

      I don’t know – if I were her, I’d be avoiding getting into a car with this kid and would never fly in a small plane with him. No skiing either.

      That bunch has a cloud of disaster hanging over their heads, although Taylor won’t be helping things.

  40. tmbg says:

    She might be stalkerish, odd and a knit-wit, but I do think she’s beautiful. I think that’s her real hair and if it is, I’d love to have it (except the color – I like lighter blonde shades).

    I still don’t get why she’s with an 18 y/o, but whatever… O_o;

  41. dreamer says:

    I have family in Greenfield (kind of run down–we’ll call it “quaint”) and Deerfield (BIG $) and a relative that attends prep school in Deerfield, although I don’t think it’s the same one that the Kennedy offspring goes to, I’m sure we would have gotten an earful about THAT.

    Prep school is, uh, different. Husband went to prep schools in Connecticut. Some (most?) have half school days on Wednesdays and Saturdays to allow for sport matches. Although the students are given some measure of free time, usually to go into town and eat and hang out, as far as I’ve heard, you can’t just cut loose when your girlfriend shows up.

    Then again, money, famous pop starlets and family names like Kennedy buy a lot of freedom, eh?

    Also, about that 18 year old junior-in-high-school thing: it’s common to take post-graduate years. Yes, in high school. Sometimes it has to do with getting more exposure from scouts for pro sports & colleges… although some of ‘em just stick around because they like the environment. I met one guy from husband’s prep school that was just graduating at twenty. Naturally, his parents gifted him with a brand new Benz.

    And that’s how the bizarre other half lives.

  42. moo says:

    Can you say Stalker?

  43. LeslieM says:

    I think it’s weird she’s dating a kid who’s still in high school. They need to hold on until he’s in college at least. I think socially and mentally she’s about 16 or 17. I know everybody here hates her but a lot of people love this girl. I think she just made some huge mistakes with the guys she’s dating it must be a weird life for her. She doesn’t seem to know anyone her own age.