How To Date Multiple People Simultaneously

Tale Of Two Terry’s
I once dated two women both named Terry, simultaneously. They lived in the same town and had similar pitched voices, which made answering the phone and hearing, “Hi, it’s Terry,” a confusing experience. This became so crazy making, that I was relieved when one of the Terries, reacting to my constant state of bewilderment, said good luck and good-bye. 

The Multiple Dating Boat
Dating multiple women felt stressful at first, until I discovered that many women were dating multiple men. That leveled the playing field for me. I’ve learned that dating multiple women takes experience, good notes, managing highs and lows, and stamina. After working all day, sorting out names, faces, and online profiles takes focused energy. But I continued on this path for a while because multiple dating presented a unique opportunity to meet a myriad of women in a short period of time.

To minimize the wear and tear on everyone involved, I became very selective.
My list of essential qualities was short; a woman who had done personal growth work, was physically active, close to my age, and appreciated the arts. I also paid close attention to women’s descriptions of the men they wanted to meet. I passed if I wasn’t a near-perfect fit. I remember one woman’s profile that seemed irresistible. Then I read that she trains horses, and I get anxious just thinking about horses, having been thrown a few times. A square peg in a round hole, for sure. I stopped saying yes to every woman who emailed me after I realized my ego was making my choices. And long-distance relationships get really old, really fast, so I dated locally.

Navigating The Maze
I found it difficult to remember a woman clearly until we actually meet. I kept notes before a coffee date, but second dates were very rare, so the notebook was thin. I don’t feel I missed much by being circumspect, because my experience with second dates, when the first was marginal, was rarely good. I learned to trust my intuition. And rather than project my wish list onto a date, I focused on the actual person sitting across from me. Of course, women crossed me off of their lists too, and feeling rejected stung because it was very personal, but it was just part of dating. My approach was an assembly line, so it’s fitting to mention how many women I dated, simultaneously.

I could email, telephone, and coffee date, three women simultaneously, but after a month of dating at this level, I needed a break. I took my profile down, rested, and regrouped. I hung out with friends, or spent time alone, and I tried not to think about dating. I limited the time I devoted to online dating to maintain perspective, but also to avoid burnout. Half an hour in an evening was my max. After that, the profiles and photos begin to blur. Smart multiple dating requires homework. Throwing darts at profiles doesn’t succeed. 

Multiple Partners
I knew in my heart that being sexual with multiple partners wouldn’t work because I preferred not to be sexual with anyone until there was enough emotional connection for a monogamous relationship. Since my ultimate goal was an intimate relationship, being sexual with more than one woman felt counterintuitive. Sex was entirely about investing my heart, and I couldn’t do that casually.

A Kid In A Candy Store
In the beginning, multiple dating online felt like sitting in front of a mountain of chocolate, but I quickly learned not to overindulge. My desire to meet someone special was a powerful force that wasn’t always easy to control. Sometimes I had to fight my libido and loneliness in order to maintain focus and date smart. Dating multiple partners, works, in terms of meeting a lot of people, but it’s not for the faint-hearted or lazy. If you decide to try it, take good notes, and remember to take a break once in a while.

I met my partner on a coffee date nearly three years ago. She was my forty-eighth coffee date in two years, admittedly a grueling schedule. But since I only had a handful of second dates during this entire period, I wasn’t really juggling relationships as much as simply finding time. In my experience multiple dating was worthwhile. I dated a lot of women, but narrowing the field was relatively easy since I knew I’d recognize “the one,” when I met her.

Visit for boomer dating articles, blogs, videos, and information about Ken’s new book, The Boomer Guide to Finding True Love Online.

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Love Magazine: How To Date Multiple People Simultaneously
How To Date Multiple People Simultaneously
Love Magazine
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