Anne Hunting Love: The Hunt Begins

Fellow Rom Com lover, let me introduce myself. 

My name is Anne Huntington and I am a lifelong devotee of romantic comedies. As a child, I would walk around my house with a book I could not read, pretending to ward off the romantic advances of Gaston, a la Belle from Beauty and the Beast. As a preteen, I spent hours with friends learning Diego Luna’s exact dance moves from Dirty Dancing Havana Nights. In high school, I performed “Elephant Love Medley” from Moulin Rouge at a school dance with the boy I was crushing on. In college and as a young adult I have traveled the world recreating scenes from favorite movies, including visiting the Golden Temple in Amritsar, India because of vital scenes from Bride and Prejudice.

My own dating life, though, never resembled the movies I loved so much. I spent a year in South Africa doing service and fell hopelessly in love with a fellow volunteer under the endless skies. I had experienced all of the classic romcom tropes I knew so well in this one-sided love story – I had sought adventure, fell for a man who at first repulsed me, fallen asleep together after talking all night. But he had grown up in a household of boys and obviously NOT seen all the movies I had because he was clearly NOT following the script: he did not love me back.

Remember Kate Winslet’s character from the beginning of The Holiday? Yeah, that was me. For those that don’t remember, simply put, I spent way too long loving someone who did not love me back. In the years of longing, I had used a number of excuses to not date – I was too busy, I had to focus on my career, I was too tired. But as I neared my 30th birthday, having spent most of my twenties trying to find ways to convince ONE particular man to love me, I knew I needed a new perspective, a new way of operating

Unfortunately I could not do a house swap with a successful producer in LA, so I had to leave Kate’s storyline and find my own.

I gave myself a challenge: go on 21 first dates within 30 days.

You read that correctly. 21 individual dates. With 21 DIFFERENT men. Within a month. Why would someone attempt something like this, you ask? She must be crazy, right? And, you would be correct. But if I had learned anything from my beloved romantic comedies, it was that the gods of romance looked lovingly on somewhat questionable antics while on a quest for love (adolescents swapping countries and lives in The Parent Trap, anyone?). And I had met someone who had successfully completed an even crazier challenge: 21 dates in 7 days (at the time I met her, she had been with date #10 for several years). 

Beyond looking for love in this challenge, though, I wanted to learn more about myself. Spending so much time focused on one person, I had missed out on testing the proverbial waters of modern dating. I did not know much about the kind of man I was looking for in a partner. Did I want someone funny? Was it important if he had a full head of hair? Was I more attracted to kindness or a six pack? Were those mutually exclusive? Did I want to fall in love or was it easier to complain about not having found it without really trying? SO. MANY. QUESTIONS. 

If I found love, that would be great (and what an awesome story to tell at our wedding, am I right?!?), but if not, I would know myself better. I would be better equipped to find and commit to a love, or to understand my life as a single woman, with more clarity. 

Before you start thinking I went all Andie from How to Lose a Guy in 10 Days, I did not go into this to hurt anyone. I really was looking for love and a partner, and in that sense, I did not lead anyone on. That being said, the majority of men did not know they were 1 of 21. Otherwise, I was very honest, letting men go as I did not feel a connection with them (to steal a line from The Bachelorette). Dating is hard, and these men were putting themselves out there as well, so I made every attempt to be extremely kind. 

With “Anne Hunting Love,” I attempted to make my own life a romantic comedy and, in the process, learned quite a lot. There were boring dates, bad dates, good dates, and more than one great date (can’t you see a montage of some of the dates right now? I feel like it would be reminiscent of the search for a best man in I Love You, Man, which is not technically a romcom, but I’ll allow it.). Each date had his own emoji, and so, without further ado, I present to you the 21 dates I went on in order: 

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Did one of these men steal my heart? Can you guess which were the best dates? The worst? Put your thoughts in the comments and keep reading to find out if you were right! 

Love, Anne


THANK. YOU. ANNE. Wow! We cannot get enough.. we want to hear about the dates already. Anne will be sharing four more in the series of Anne Hunting Love:

  • The 5 Most Boring Dates and What She Learned

  • The 5 Worst Dates and What She Learned

  • The 5 Best Dates and What She Learned

  • What S Learned Overall and An Update/Dating in a Pandemic (Is she staying in touch with anyone?)


To see more from Anne, and follow along with the podcast version of Anne Hunting Love click the links below:

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Anne Huntington