Dating Story

I’m A Millennial Woman Who Loves Dating Multiple Men

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As your typical Disney Princess/fairytale lover, I’ve always been a relationship gal. I’ve dreamt of my happily ever after with my very own Prince Charming ever since I was a little girl.

In kindergarten it was Mark. We sealed the deal at my Chuck E Cheese birthday party. His gift definitely helped; it was the most fabulous Barbie with matching accessories to boot. But things didn’t last with Mark. I moved up to the first grade and he moved across the country.

Before I knew it, I was in junior high school and found myself in a dating frenzy. There was Keith; we dated the summer before 8th grade and our relationship lasted as long as the opening sequence to Grease. There was Joe; he was my first official boyfriend and the first jerk to break my pre-pubescent heart. As it turns out, I was simply the pawn in a very complicated game of chess between Joe and his on again/off again girlfriend.

Yet I never took a break from dating. If it wasn’t Joe, or Keith or Mark, it was Shawn, Danny, and tons of potentials in between. I loved the comfort of coupledom. I was so in love with being in a relationship that I found myself in relationships just to be in one. By the middle of 9th grade I nabbed another boyfriend. Then a brand new way of life presented itself when not one ex but two exes popped back into my life. And both wanted to try again! So I did what any 14-year-old girl would do when faced with something like this – I said yes to both guys.

In a matter of days I went from monogamy to three boyfriends – and I loved every minute of it. You see, I’ve always had this theory that love was, is and always will be the answer to everything. Here I was presented with this rare (and very unethical) opportunity. Screw a fairytale ending; I wanted to be loved and adored. I wanted to be spoiled rotten with love and affection. Yes, I was being young and selfish, but at 15 years old I felt I had found the key to my happiness. I would hang up the phone with one boy and get a call from the other. I’d see one guy at school, one after school and one on the weekends to make sure they all received equal amounts of attention (and that they’d never suspect a damn thing). Luckily, they all went to different schools in different areas and had similar names, so I was always able to juggle the mania with ease. I even started dating a fourth guy.

Let me be frank: I had no idea what the hell I was doing. Women (young or old) rarely pull stunts like these. Usually, the guys do the playing. I was calling the shots and it felt good. I felt a different kind of freedom and power when dating freely. A freedom I never experienced when constantly booed up. Because you sacrifice certain things as a couple. I just wasn’t ready to make that commitment.

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So I continued with this pattern while in college at Hofstra University. When one guy would exit, another ex or new flame would pop up like clockwork, and I’d casually date one guy after another in consistent and constant rotation. I had it down to a science and made sure I’d adhere to certain rules, like dating no more than two guys at a time and cutting off the relationship if and when it felt too serious. Now in my mid 20s I’ve continued to embrace being the Queen of Non Commitment. The thought of being tied down causes me to break out in hives.

I’m not giving up on monogamy all together. I just need to do me for a while. While I wait for my happily ever after, I figure I might as well enjoy the ride and kiss a few more (very cute) frogs.

Tiffani is a true city gal, hailing from the concrete jungle of New York City. With a large coffee in tow (that’s pronounced caw-fee to my non-New Yorkers) this closeted “self-help” addict and Lifestyles writer is on a continuous quest to discover how to have the best romantic life. An old soul with new age sarcasm, Tiffani’s sharp, witty and tell-it-like-it-is attitude has resulted in many a snafu as she tries to navigate and conquer the most challenging and complicated assignment of all: dating the New York City man. Come a long for the ride as this seasoned serial dater tries to find balance between her journey to self-love and her old school values on dating and relationships. She writes about her lessons and adventures in dating as a twenty-something millennial and all the new rules that apply.