Category Archives: Relationships

Happy Valentine’s Day Weekend!

I know this day of serious PDA, mushy poems, and the smell of “love” in the air can be an annoying holiday for some people BUT I still thought it would be nice  to give all of you prepsters a Valentines Day Weekend Gift Guide and an Activity List of things to do no matter if you’re single or in a relationship. You may have forgotten to get that special someone a gift on Thursday and I wish you the best of luck with all of your attempts for redemption this weekend!

Valentine’s Day Weekend Gift Guide:

For Her:

  • Lilly’s New White Dress Collection

Wishlist lilly






  • The Best Bouquet She’ll Ever Receive








  • Studs from Tiffany’s




  • Chocolate, Duh!







For Him:

  • Cigar Chocolates

Choc. Cigars







  • Bow Ties






  • Tickets to See His Favorite Band/Team Play







  • A Nice Watch







Valentine’s Day Weekend Activities:

If You’re Romantically Involved:

  • Do the whole mushy, romantic dinner at a fancy restaurant and surprise each other with gifts
  • Go out on the boat for a night
  • Do something you’re both scared of
  • Spend the night in getting warmed up by the fire
  • Reenact your first date
  • Go ice skating together/play in the snow

If You’re Single & Loving It:

  • Grab your friends and go out
  • Have a fun night in with movies and your favorite treats
  • Write Valentine’s Day cards to soldiers or children
  • Spend the night with family making sure they know how much you love them
  • Go to an “Anti-Valentine’s Day” Party
  • Tell your crush you’re into him/her with a decorative cupcake

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KillSwitch App Release

KillSwitch: The app that seamlessly and discretely removes traces of your ex from your Facebook profile!”

This Valentine’s Day, the KillSwitch app will release! Some questions obviously are running through your mind as you are reading this. Why do I care? Why is The Boss posting this? Well, I got the chance to talk to the co-founders, Clara and Erica, of KillSwitch and learned some pretty cool stuff about the app!

How did you get the idea to start up KillSwitch?
My co-founder, Erica Mannherz, and I have this one friend who every time she breaks up with her boyfriend, deactivates her FB account. It would take her forever to finally get up the nerve to re-activate and even then, it was a super painful process having to go through the minefield of FB pictures where she was still tagged w/her ex–reminders of when she was happy and in love. We couldn’t believe that there wasn’t a mechanism in place to account for this–after all, we live so much of our lives digitally now, and a big part of life is the end of relationships! So we invented KillSwitch, as a way to help people move on and reclaim that little corner of the internet you call your own (your FB profile).

With the small student bodies at private schools, how can KillSwitch help smooth over break ups on Facebook?
Quoteth Erica:  “The biggest bonus of KillSwitch is that fresh start. It’s hard enough trying to avoid your ex in the small student bodies of prep schools, why should you face the same challenges in your digital life as well? More than anything, it’s a way to really start a-new when you go on to college, an opportunity to meet new people and form opinions based on in-person interactions, not last year’s prom date.”
What is the best Valentine’s Day Gift you’ve ever received?
I can’t say there’s ever been a stand-out in Valentine’s Day gifts I’ve *received* (pretty standard jewelry, etc.) but I did *give* a pretty rad Valentine’s Day gift last year–I sent my long distance beau a taxidermied piraña with the note “you eat my heart alive.” 

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Preppiest Couple West of the Mississippi

Hi all! Based on my incessant habit of Instagramming (we can make it a verb, right?) this week, some of you may have picked up that my senior year Winter Formal took place last Friday, February 1st.  I guest posted for Grace from the blog Preppy on the West Coast this week and talked about everything from asking my date, to finding a location, to what everyone wore.  Click over to her blog to read all about it!

Everyone knows that the best part of a school dance is taking pictures with your date and getting to post them everywhere, so I’m taking full advantage of that.  We hired a photographer and took pictures at Balboa Yacht Club, looking over Newport Harbor. These are the results:


 We’ll pretend that the boutonniere didn’t poke him…


On him: shirt, Vineyard Vines | bow tie, Vineyard Vines

On her: dress, Lilly Pulitzer | belt, Another Line |shoes, Steve Madden

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Taylor Swift dumps Deerfield junior

Say it ain’t so!

OK, so he is a repeat junior. Still, to be a junior at Deerfield and to have dated Taylor Swift definitely pumps up your cred and makes you achieve legend status amongst your bros. The word is that Taylor Swift will record and release a new album in the next week, and the top single will be “I will never, ever, ever date a prep school student again (ever).”

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Deerfield bro hooks up with Taylor Swift

THERE’s your headline!

Absolutely the worst looking bikini I have ever seen. Literally the worst look ever, and if other girls start copying it, I will be crushed.

Everywhere I turned on Cape Cod, I could not escape the headlines about Taylor Swift snuggling with Conor Kennedy. In case you are living under a rock and only briefly emerged for some Sunny Delite and Pop-Tarts, Conor Kennedy is the grandson of Robert F. Kennedy. He is also a JUNIOR at Deerfield Academy, a legendary prep school in Massachusetts.

The newspaper headlines have been abuzz about Kennedy and his GF Taylor Swift crashing his cousin’s wedding, and the bride’s mother getting all up in arms about it.

Personally, I do not get Taylor Swift. Yeah, you have been in love. You have been dumped. Get over it. There are about a dozen girls in my school who are easily better looking than Taylor Swift. If they could sing and write crappy songs, they would be multi-millionaires (on their own, not counting their family money). 

The REAL headline should be that a Deerfield Academy student is hooking up with Taylor Swift. That is your hook-up hero right there! How much of a god will Conor Kennedy be next month when he gets back to Deerfield? Do you think that his bros will be hitting him up for details?

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Filed under Girls, Guys, Prep School Life, Relationships

The Confessions of trueprep

Dear Readers,

I have a confession. I was trifling through my things getting ready to leave my house for a day trip and came to the realization that I have a serious problem. It’s called monogramitis. This terrible disease is basically the need to monogram everything one owns. From pillow cases to gym shorts to my backpack, I have my initials on practically everything. Not only is monogramitis a personal issue, but it is infectious and has caused many of my friends to start down its dangerous path. It has proven quite difficult for me not to adore things that are specifically mine and cannot be mistaken for anyone else’s so I have decided that, despite how risky this is, I need to share my love of monogrammed items with all of you. I have found Converse shoes, iPhone cases, virtually indestructible “Roadie” cups, and rain boots that can be monogrammed to your liking. (By the way, Vineyard Vines also has phone cases that make me happier than a five-year-old in Disney World.) If monogrammed things aren’t for you, that’s fine too. I discovered some classy knit bow ties to keep you/your guy’s preppy neck warm for the fall and winter and some tacky shorts to watch the London Olympics in. Enjoy!

Send in pictures of your favorite monogrammed item to the Twines & Vines Twitter page and you may be featured on our Instagram!

<3 Stay Preppy


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Filed under College, Fashion, Girls, Guys, Prep School Life, Random, Relationships, Swag for the gents, Swag for the ladies, Technology, Travel, Uncategorized

What will a girl do for five dollars?

One of the funniest websites I have seen is, where you can get girls to flirt with you, friend you on Facebook and pretend to like you, or help you with your homework for only $5.00.

If some guy out there will pay just one girl five bucks to fake flirt with them on Facebook, then the founder of that website is an absolute genius. I am just mad that I didn’t think of it first.

I can only assume the dorm room prep crowd would have a blast procrastinating with this.


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