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The Art Of Dating Around


Lots of people these days see more than one person at a time. Here, the new etiquette for playing the field.

By Phineas Mollod and Jason Tesauro

n this multi-tasking era we live in, it’s not unusual for single folk to date more than one person. We think of it as a situation comparable to multi-ball play in pinball: the pulse-quickening sequence when a horde of extra silver balls forces your flippers into rapid-fire duty. For many, this leads to paralyzing panic and a quick trio of lost balls down the gutter. For deft others, however, this call to arms leads to a coordinated dance of agile hips and fingers that successfully juggle several balls to high-score status.

Now, back to the dating world (especially the online universe), where some singles have a bustling social calendar that features more than one active, ongoing romance. How can
The idea of seeing other people makes most daters squirm, especially if they have a jealous streak or worry about playing second fiddle.
a person date this way without getting frazzled, confused and creating awkward, sitcom-worthy moments? And how can one do so without compromising one’s own morals or those of the sweeties involved? Allow us to explain.

The benefits of multi-dating
Multi-dating isn’t merely a tactic for doubling your pleasure. Rather, during your hunt for The One, it can be a way to achieve romantic wholeness by dating partners with differing interests and personalities. Whereas one partner tickles your hike and mountain bike fancy, another prefers your penchant for the opera and fancy dress. Instead of forgoing a relationship with someone who only meets half of your needs, you can enjoy yoga and yogurt with one date; raves and rib eyes with the other and discover with which amour you really click best.

Indeed, by expanding your romantic options, multi-dating can loosen up your definition of your type and help you mingle with the vast array of potential mates out there. These days, with high expectations for chemistry and shared interests, some people toss away a good thing because their partner isn’t a 100% perfect match. Multi-dating encourages you to recognize the infinite array of people out there...and realize that perhaps one’s dating checklist of “must-have” qualities isn’t to be followed too closely.

What to tell your dates
The idea of seeing other people makes most daters squirm. If they have a jealous streak or worry about playing second fiddle, it can be a bitter pill indeed. During the first month of easy dating (as opposed to a serious-from-the-start romance), gauge your partner’s potential willingness to share your heart. While no one is suggesting you start a date by offering, “Pleased to meet you; I’m Dan and I’m currently dating two other women,” you do need to share viewpoints and disclose your actions as the relationship unfolds. How, exactly? By steering a conversation around the following topics:
  1. Both of your thoughts on whether a healthy relationship can exist without monogamy.
  2. Both of your beliefs about whether courtship is always a prelude to marriage.
  3. Both of your reactions to a statement like, “While youth is wasted on the young, curiosity isn’t.”
When the going gets physical…
And what if the above topics don’t present themselves at a convenient moment over pad thai? As dating turns intimate, it’s time to fess up. Before you ever open your
Don’t get caught up in discussions of “Who’s a better kisser?” or “Why aren’t I enough for you?”
mouth, your mate may ask if you’re seeing anyone else—this is the perfect segue for the truth. However, only the cad waits to be let off the hook. Your dating life should be noble, not nefarious, and it is consent that separates the gentleman from a bed-jumping gigolo. Most importantly, consent spares all parties the turmoil of a secret love triangle gone sour. Coming clean need not be terrifically awkward: “I’m really enjoying this…and before we go any further, I want you to know that I’m seeing other people.”

Once the word is out, it’s reckoning time. Don’t get caught up in discussions of “Who’s a better kisser?” or “Why aren’t I enough for you?” Explain why multi-dating is working for you now and why you’re not ready to change your ways…then handle the fallout. Some mates refuse to compromise and share their honeybunch with anyone, and that’s fine; others don’t care or are multi-dating as well, and still others will stick it out for a spell to see if they can win over their reluctant Romeo.

Two particular challenges to be reckoned with: First, the heat from a budding relationship often morphs into a natural desire for exclusivity. There’s no fighting gravity’s pull, and at this point, it’s either time to commit or step away from the fantasy. Also to be contended with is the dreaded double-standard, which occurs when one partner declares his own freedom to date around while simultaneously forbidding his mate the same prerogative. This may have worked for your great-grandfather, but unless you’re richer than a sultan, it’s time to greet the 21st century …it’ll be around for awhile, and the double-standard won’t be.

Some final tips
  • Especially within your own office, dating both Amber from Accounting and Meghan from Marketing is petty and perilous…you have a better chance of jumping Snake River Canyon on the back of Evel Knievel’s rocket-powered bike than pulling off that bit of rompery.
  • Pet names, romantic notions, or nightstand goodies must remain personal. Despite 2-for-1 offers on a dozen roses, don’t reduce woo to a cheap form letter of repeat gifts and affections. As you suss out your dating options, each woman you see deserves to be courted as the lovely individual she is.


Phineas Mollod traded his J.D. for the editorial life and is often found riding the congested E train with his wife and daughter in New York. Jason Tesauro pushes pen and ink by day and leads the MGAffairs.com lifestyle seminar series by night, ne'er far from his sweetheart and a Brady Bunch houseful 'o tots in Virginia. Together they are the authors of The Modern Gentleman: A Guide to Essential Manners, Savvy and Vice and The Modern Lover: A Playbook for Suitors, Spouses, and Ringless Carousers.
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