How to Play the Field to Win in Online Dating

Tips on Dating More Than One Person at a Time

The reality of online dating brings certain things with it that conventional dating does not:

  • We all hope to find a partner that we can settle in with a have an actual relationship
  • We all have put up a profile in an effort to attract a potential partner with the hopes of attracting as many candidates as possible
  • Everyone is talking to or corresponding with more than one person
  • Online dating is like trolling, you keep a line in the water at all times

So knowing these are inevitable truths that are universal to anyone on the site, act accordingly.  We’re all here for the same reasons, and there’s just no way to tell despite those individuals whose goal is seemingly to have only an email or Instant message relationship, that you really don’t know how interested you are in someone until you meet them.  Even then, anyone can put up a good front and their best foot forward for one or two meetings.  So why put all your eggs in one basket?  Undoubtedly anyone you date has one or two things about them or their situation you find less than ideal or appealing.

Where to Begin

This could never be truer than when you first put your profile up on a new site.  One thing being on these dating sites teaches you with time is that more often than not, the same damn people keep showing up within your mileage parameters under your saved search menu.  So when a newbie arrives, all of us seasoned folks in the area click away.  If the potential new comer is even slightly attractive, and is able to string together a paragraph or two that displays at least average intelligence, they are certain to attract more than a little action.  Does this mean you should refrain from contacting them?  Absolutely not, but what it does mean is that if you want to stand out amongst the dyke deluge or the man monsoon you’d be best to play it cool.  Remember when you were the newbie and didn’t know jack about how the “scene” worked.  It took you a month or two to figure out that some of these lame players use form letters and play a numbers game, particularly the better looking singles.  So to stand out welcome the newbie to the site and go with the polite inquirer route.  Mention some ways that the scene is a bit uncomfortable and that you wish them good luck, and that you’d simply like to know more about them.

But what if it’s you that are the newbie, or you just changed your profile and for whatever reason have hit a cord with the opposite sex (as all sex originates in the mind) and find yourself swimming in options of potentials, is it ok to go out with them all?  Hell yes it is, isn’t that what you’re on the site for??  To find your prince (or princess) you may need to kiss a few toads, the bottom line?  You can’t win if you don’t play.  So how then do you manage more than one at a time and what is the right number to take on at once?  I found a recent Cosmo post with a rare piece of wisdom that happens to match what I am a proponent of anyways, the tidbit…”keep a pair, with one to spare”.  That’s right, forget three being a crowd, it’s not like they will ever be all together at once, so play the field and hold open your options.

How to Stay on Top of Things

But how to manage such activity?  Well let’s explore why it’s a good idea, which is more important than the how.  Human nature is to A-want what we can’t have and B-Pursue the law of scarcity.  That’s right, why is it we find we can’t live without our ex, the same ex that was making us miserable, and the minute they break things off?  Because as humans we want what we can’t have.  Say I can’t have something, and stand back and watch me get it.  This is subconsciously what we all revert to as humans.  And it plays right into the law of scarcity.  Simply put, who is more attractive; the man you ask out who would like to go out, but is booked for this weekend, or the dude that emails you and asks if you have plans for tonight or tomorrow, they are free either night?  Simple. There’s more intrigue with the one who is in demand.  So then knowing that is true universally for us all, is it not a good strategy then to play the field, even if you long for a single soul mate with which you can curl up on the couch with, unless you put yourself out there and immerse yourself in getting your feet wet, you’ll never find the “one” from behind your screen.

Be Busy, but Make Sure you have Free Nights

So that’s the why, here’s the how.  If three is the magic number, how do you manage your time?  Well, with three the one thing for sure is you’re going to be busy.  Busy is good because it keeps you from appearing desperate when you correspond or meet with any of the potentials.  Why my personal opinion is you be honest if asked directly if you are seeing more than one (after all, the benefits to them knowing you’re in demand can’t work for you if they don’t know), some prefer to keep it all on the down low.  While certainly you want to exercise a bit of class and not advertise that you’re going out with multiple people all week long, when one of your hopefuls waits till Thursday to see if you are busy Friday, a simple, “Oh, I’d really like to go out with you, and I’m glad you asked, but Friday’s no good for me, I’ve already made plans, how’s Saturday for you?”  There’s certainly no obligation to divulge that you’re already set to meet another hottie for a drink, but the subliminal message is there…”I’m in demand, if you want time with me you’ll have to call more in advance”.

So if you’re following the “keep a pair with one to spare” advice already what if you’re booked already for both Friday and Saturday (as ideally you will be, and if not you’re considering saying you are to look more appealing).  You can respond with, “Gee I guess I’m a bit of a planner and I’ve already made plans for this weekend, but we could meet for coffee Sunday, or perhaps one night next week?”  Now you’re putting the laws of human nature to work for you.


Accepting that all is fair in love and war, unless your intimate with what you suspect may be a keeper, you’re under no obligation to limit yourself to just one potential.  Whether stud or dud, your confidence can only grow with the more dates you go on: nothing is more sexy than confidence, not arrogance, confidence.  Others can perceive when all is not waged on whether the evening you spend together will determine more than if you are open to a connection, but that you’re secure in yourself if things are not sparking.  So step out from behind the screen, keep class in mind and don’t blatantly advertise that you’ve more than one option, but certainly don’t pass up the opportunity to politely mention that until you reach the intimacy stage, you’re not limiting yourself.