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Date Knight: Should single women date more than one man?

As the staff’s resident relationship guru — who’s carved out a space on the web with an award-winning site called Naked With Socks On — I’ve been tapped by JET’s EIC to offer up dating advice and perspective each week for our readers. Five days out of the week I’m slaving behind a desk as JET’s Managing Editor, so I look forward to exploring the sights and sounds of Chicago with my wife as part of our weekly outings. I am Anslem Samuel Rocque and this is Date Knight.


I came across an interesting article the other day about a new book called The Gaggle. Written by Jessica Massa, who, along with Rebecca Wiegand, runs the website “WTF Is Up With My Love Life?!,” the book discusses the idea that many women do a disservice to their dating lives by limiting themselves to one potential suitor. From my understanding, the author(s) are not suggesting that a woman be “loose” but putting all of ones eggs in a single basket is not an effective way to find your soul mate.

The alternative is to have a “gaggle” of men in your dating circle. In theory, each one will fulfill a different emotional need as you search for “the one.”

“You probably have a gaggle of friends, who all play different roles and fulfill different needs for you,” Massa explains. “You might call one friend to go shopping versus another friend when you’re upset versus another friend when you need a serious professional opinion. Your romantic gaggle is just another piece of the much larger, long-term puzzle of how you structure the relationships in your life to feel full, happy and loved.”


She goes on to say:

“As a woman, having a gaggle provides you with a love life full of possibility: you have many men in your life, in many ambiguous but enriching ways, who are all teaching you about yourself and your needs and desires and leading you closer to the guy and relationship you want.”


It’s an interesting concept that appears to have some merit, but I’m not sure it’s a universal approach that will work for every woman. Morals and background will likely play a role in how the “gaggle” rule would play out.

But what are your thoughts? Do you think that single women will have better relationship success if they dated more than one man at a time?

Share your thoughts in the comments section.