July 27, 2008 - IT'S time. I'm done. I've had it. I'm through. "We have to talk," I tell Super Preppy, and I'm getting choked up before I even begin. Truthfully, I think from the...more >

July 20, 2008 - Super Preppy and I are leaning into Amma, the "hugging saint" who's come to visit New York all the way from India - receiving a blessing as a couple. Wearing smart, brightly...more >

July 13, 2008 - IN New York, celebrities abound. So much so that it's actually not that hard to date - or fool around with - them. I've gone out with Moby (he sniffed my neck!), had a drunken rendezvous...more >

July 6, 2008 - ONE year ago, I was e-mailing Super Preppy with an invite to a swanky penthouse party for July Fourth and nervously dropping $800 at Banana Republic in my attempt to try to find the right "...more >

June 29, 2008 - I'M saying goodbye. Super Preppy is settling into the boat he's about to call home for the next six days. I'm pacing the dock, trying to look glamorous instead of exhausted and trying to...more >

June 22, 2008 - IT could have been a fling. Most people must have been betting on that.And yet, here it is nearly a year later, and I'm dating the same man - Super Preppy (yes, I thought it would be a throwaway...more >

June 15, 2008 - "HE has trouble saying 'I love you,' " I complained to my friend Sara recently over Sunday brunch, drowning my sorrows in a mimosa. "But he does say 'Miss you' a lot...more >

June 8, 2008 - I became so paralyzed by depression last week that I couldn't breathe.I sent off an e-mail to three or four of my closest girlfriends.My fingers sluggishly typed: "I am considering running...more >

June 1, 2008 - ''I'M quite a romantic," says the Serial Monogamist, who, hilariously, also happens to be roommates with the Legendary Bachelor - a k a the real-life Chuck Bass. "I like my...more >

May 25, 2008 - "I was locked in a sex dungeon with a dead horse, two underage Thai hookers, some methamphetamines and an industrial-sized tub of Vaseline," the Legendary (and Might I Add, Well-Respected)...more >

May 18, 2008 - 'LITTLE Mandy," Super Preppy says, touching my face as we wake up in the morning. "Little, little Mandy.""That joke never gets old, does it?" I ask."Nope," he...more >

May 11, 2008 - WALKING around Chicago is like walking around with ghosts. It's just me - Super Preppy's off on a business trip to Europe, and all I have is my memory and the cold chill of self-pity...more >

May 4, 2008 - MY ex-husband was a musician. And I finally had the courage recently to play one of his songs for Super Preppy.SP was kind and patient, loving and thoughtful, squeezing my hand as he always does...more >

April 27, 2008 - I am wicked jealous. My friend Lisa has apparently found Mr. Perfect. I didn't even know I was capable of this kind of jealousy. I think it was the toothbrush story that did it. "When...more >

April 20, 2008 - I'M sick of being such a drama queen.Here's a typical every-21-days-or-so conversation between Super Preppy and me - always instigated by yours truly, thank you very much."Just so you...more >

April 13, 2008 - "YOU have it," my friend Missy whispers to me over drinks one night at The Spotted Pig. "You have the mojo!"She's a little drunk, she's extra hot and she seals the...more >

April 6, 2008 - IT'S official. I'm "in a relationship" on Facebook.There's no going back now.And if there is, it will involve a humiliating broken cartoon heart on my mini-newsfeed to...more >

March 30, 2008 - "LONG ago I figured out the path to having a great relationship," my remarkably confident, maddeningly wise, six-times-proposed-to Aunt Deb tells me on the phone from her home in Portland...more >

March 23, 2008 - THE HOT YOUNG Thing is devastated.After spending a romantic weekend with a potential Mr. Perfect in Las Vegas, this busty bombshell fell hard for the young real-estate mogul she described as being...more >

March 16, 2008 - "CONGRATULATIONS," the card attached to a gorgeous display of red, pink and yellow roses reads. "You're going to Jamaica!"Is it for me?Dude, I wish.No, it's for my...more >

March 9, 2008 - IT'S 2:45 a.m., and the text message to my friend Jonny is way, way NSFW.To protect the woman's identity, let's just call her "Subtle in New York.""Make it to me. With...more >

March 2, 2008 - SOMETHING amazing has happened.The weight is gone.It's been replaced, almost entirely, with a sense of peace and joy and love.And no, I have not joined a cult."I'm going to be honest...more >

June 8, 2008 - I became so paralyzed by depression last week that I couldn't breathe.I sent off an e-mail to three or four of my closest girlfriends.My fingers sluggishly typed: "I am considering running...more >

June 1, 2008 - ''I'M quite a romantic," says the Serial Monogamist, who, hilariously, also happens to be roommates with the Legendary Bachelor - a k a the real-life Chuck Bass. "I like my...more >

May 25, 2008 - "I was locked in a sex dungeon with a dead horse, two underage Thai hookers, some methamphetamines and an industrial-sized tub of Vaseline," the Legendary (and Might I Add, Well-Respected)...more >

May 18, 2008 - 'LITTLE Mandy," Super Preppy says, touching my face as we wake up in the morning. "Little, little Mandy.""That joke never gets old, does it?" I ask."Nope," he...more >

May 11, 2008 - WALKING around Chicago is like walking around with ghosts. It's just me - Super Preppy's off on a business trip to Europe, and all I have is my memory and the cold chill of self-pity...more >

May 4, 2008 - MY ex-husband was a musician. And I finally had the courage recently to play one of his songs for Super Preppy.SP was kind and patient, loving and thoughtful, squeezing my hand as he always does...more >

April 27, 2008 - I am wicked jealous. My friend Lisa has apparently found Mr. Perfect. I didn't even know I was capable of this kind of jealousy. I think it was the toothbrush story that did it. "When...more >

April 20, 2008 - I'M sick of being such a drama queen.Here's a typical every-21-days-or-so conversation between Super Preppy and me - always instigated by yours truly, thank you very much."Just so you...more >

April 13, 2008 - "YOU have it," my friend Missy whispers to me over drinks one night at The Spotted Pig. "You have the mojo!"She's a little drunk, she's extra hot and she seals the...more >

April 6, 2008 - IT'S official. I'm "in a relationship" on Facebook.There's no going back now.And if there is, it will involve a humiliating broken cartoon heart on my mini-newsfeed to...more >

March 30, 2008 - "LONG ago I figured out the path to having a great relationship," my remarkably confident, maddeningly wise, six-times-proposed-to Aunt Deb tells me on the phone from her home in Portland...more >

March 23, 2008 - THE HOT YOUNG Thing is devastated.After spending a romantic weekend with a potential Mr. Perfect in Las Vegas, this busty bombshell fell hard for the young real-estate mogul she described as being...more >

March 16, 2008 - "CONGRATULATIONS," the card attached to a gorgeous display of red, pink and yellow roses reads. "You're going to Jamaica!"Is it for me?Dude, I wish.No, it's for my...more >

March 9, 2008 - IT'S 2:45 a.m., and the text message to my friend Jonny is way, way NSFW.To protect the woman's identity, let's just call her "Subtle in New York.""Make it to me. With...more >

March 2, 2008 - SOMETHING amazing has happened.The weight is gone.It's been replaced, almost entirely, with a sense of peace and joy and love.And no, I have not joined a cult."I'm going to be honest...more >

February 24, 2008 - AND now for a word from my Voice of Reason."We're neurologically wired to never be content," advises Dr. Rob Reiner, my favorite relationship psychologist.I'm updating him on my...more >

February 17, 2008 - WE'RE in paradise. And I'm puking my guts out."Was it something you ate?" Super Preppy asks from the main room of the gorgeous resort where we're staying in Arraial d'Ajuda...more >

February 10, 2008 - MY answer is always the same. Women like confidence. "All the girls are gorgeous in the part of Brazil we're visiting," I tell Super Preppy as we prepare for vacation in Porto Seguro...more >

February 3, 2008 - "I'M really enjoying this," Mackenzie e-mails me as she hears me talking to a very young, very pretty, very busty girl who's telling me all about the trials and tribulations of life...more >

January 27, 2008 - WOW, that psychic totally didn't recognize me," I tell my friend Jon Friedman as we are walking down the street in Park Slope past a young woman who's busily chatting on her cellphone...more >

January 13, 2008 - MY complexion's breaking out right now. My roots are showing big time. My eyes look like I could hide loose change in the puffy bags underneath them. The good news: I've reached that stage...more >

January 6, 2008 - WE are awkward sometimes, Super Preppy and I. "10, 9, 8, 7..." It's 2008, and in the time between when the clock hits midnight and we actually kiss, a small manifesto could be written...more >

December 30, 2007 - IT feels like prom. Except worse. If there is such a thing. I'm in San Diego, home for the holidays, and my mom is sitting in our living room watching me freak out in the minutes before Super...more >

December 23, 2007 - MY hands are completely covered in sap. Sticky, dirty, jacket-ruining sap. And I've never been happier. “Do you like this one?" asks a Christmas tree seller on Second Avenue. “It's OK...more >

December 16, 2007 - WE'RE sitting on the beach in Miami, it's around 10 p.m. Super Preppy's head is resting in my lap, the waves are rushing toward us, and no one else is around. I feel like I'm about...more >

December 9, 2007 - THE bubble has popped. The infatuation bubble has popped, and now we're getting to find out what this relationship is really made of. “Are you having fun?" Super Preppy asks as we hop from...more >

December 2, 2007 - About last night"NO, you can't see it, no way," I say, pulling away from Super Preppy on the cream couch at his house in East Hampton on a dazzling, chilly weekend evening spent far...more >

November 25, 2007 - LOVE, LUST, LIKE - they keep you up at night. But it's your friends who help you sleep. So for this Thanksgiving - a holiday I'm grateful to be spending with Super Preppy and his family -...more >

November 18, 2007 - IT'S happened four, maybe five times now. "Good evening," Super Preppy's different doormen say warmly, waving me in without announcement. "I'm here to see -" I begin...more >

November 11, 2007 - OH, Game. So necessary and so evil. We've all heard the advice: Make him think you're unavailable. Make him think that you could disappear at any moment. Make him think you're not going...more >

November 4, 2007 - “MACKENZIE and I have done some serious talking," I e-mail Super Preppy and copy her two days before Halloween. “She is going to buy a sexy nurse outfit like mine. We think we'll go very...more >

October 28, 2007 - "I have 30 minutes to make my room look like I'm someone who has her life completely figured out," I tell my roommate Carla as we stare at my bed - covered entirely in books, magazines...more >

October 21, 2007 - "YOU remind me of my daughter," my philosophizing auto mechanic Joe Thomas told me just days before my big life-changing move from Chicago to New York two years ago. "I have a daughter...more >

October 14, 2007 - IT'S an e-mail chain I've forwarded to more girlfriends than I can count, one that started with the simple question: "How did you meet Super Preppy - a guy that you finally like?"...more >

October 7, 2007 - "OH, I remember that phase in your dating," Mackenzie tells me as I revisit the Little Shop of Dating Horrors that is my e-mail in-box. "You know who my favorite guy was? The guy who...more >

September 30, 2007 - "PLEASE text me later with fun things to do that will get me laid," my friend Julie writes me minutes before I'm about to leave for East Hampton with Super Preppy for one final stab at...more >

September 23, 2007 - WE are playing house. We've done it before, but this time it's for real. "Here's an idea," I suggest to Super Preppy when it becomes clear his summer home in Newport, R.I., is...more >

September 16, 2007 - ‘GET out of the car, you f---ing yuppie!” the Fat Man in the Ferrari is yelling at Super Preppy as we hurry to make a sailing race in the Hamptons. Yes, yes. I know. The irony is not lost on us...more >

September 9, 2007 - SUPER Preppy and I are on the last night of our long holiday weekend - three days in Newport, R.I., and then three more at a small inn overlooking the ocean in Maine. It’s been a vacation of falling...more >

September 2, 2007 - ‘YOU don’t hate women,” I say to Super Preppy. “It’s nice.” Nice is an understatement. More like, restorative of faith in all humankind. Here’s a quick little key to The Men You Will Date. The vast...more >

August 26, 2007 - ‘SUPER Preppy always has a beautiful lady with him,” an older gentleman observes as the two of us mingle with the blue-jacket, gold-button set. We’re away for the weekend again, relaxing at his beach...more >

August 19, 2007 - I call it Mistress of the Universe Syndrome Experience. It's not love. It's more than like. It's less than infatuation. It's the thing that makes you strut down the street with a...more >

August 12, 2007 - Aguy I blew off months ago won’t leave me alone. Even though we haven’t had That Talk yet, I feel funny dating anyone besides Super Preppy right now. But still, I get e-mails - almost weekly - from...more >

August 5, 2007 - ‘YOU’RE wearing a $20,000 dress,” Super Preppy’s Hysterical Friend is saying as we drink our millionth cocktail on the deck of his summer home in Newport, R.I. “But you’re with a $10,000 man...more >

July 29, 2007 - I would like to think that when I die, I will be remembered for The One Great Contribution I Ever Made To Humanity - reprogramming a man’s name to Exactly How You Feel About Him in your cellphone...more >

July 22, 2007 - ‘YOUR boyfriend wants you,” the yacht club ladies are telling me as I try desperately to adjust to the idea of hanging out with yacht club ladies in the Hamptons. “He wants you in his boat with him.”...more >

July 15, 2007 - ‘NICE talking to you the other day,” reads the message from the handsome mid-40s Married Guy. A week ago he’d worked his way into the conversation during my date with a Good Jewish Boy. I gave him...more >

July 8, 2007 - 'DID you say that you were divorced on your dating profile?" Super Preppy is asking me over drinks at the Hudson Hotel's Library Bar."Maybe not," I say, realizing how much...more >

July 1, 2007 - ‘WHEN you smile,” says the first man I’ve had insane chemistry with in forever, as he leans in close, “you ooze sex.” We are on the subway. I laugh out loud. “But men don’t want that,” I say with...more >