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Playing the Field: A Guide to Dating the Right Way.

Updated on April 25, 2015

Dating Multiple People Isn't Right For Everyone

So you found yourself dating five people and you're in over your head or maybe you want to date five people but don't want to hurt anyone's feelings. Well best believe there is a right way to play the field; and when done correctly, everyone can walk away happy. Playing the field works best when you intend to have a serious relationship and you're just looking for "the right one." Before I tell you my take of how to properly play the field its only fair to weigh the pros and cons. Pros of playing the field is that you're able to experiment. You can see what you do and don't like. You won't become too invested in one person too fast and rejection won't hurt as badly because you didn't put all your eggs in one basket. Cons to playing the field is that if it's done incorrectly, feelings can get hurt, std risks may increase if you choose to be intimate with more than one person and you may let potential candidates go faster because you know you have someone else who can fill the spot. If you're well prepared these cons won't be much of an issue. Now you're probably wondering how to be prepared. Following these simple guidelines should help to make playing the field an enjoyable experience.

Honesty Is Key!

Being honest from the beginning is probably the most important thing when dating multiple people. Make it clear to the person of interest that you are in fact dating other people and that your relationship with them is not exclusive. More than likely they too are dating other people. If the person seems unhappy you may want to try explaining that you just met and you don't want to fully commit until you both mutually like each other to that extent. Remember, when you're not honest, people tend to get hurt or confused. It's easier to make your intentions clear in the beginning. Be prepared to lose prospective dates, not everyone will agree with your point of view.

Time Management

This is probably a section in which many people fail to juggle multiple dates. Be sure not to overbook or risk standing up a date. When making plans to see someone in your rotation, keep everything tentative as not to overbook. Beware, there will be times in which you asked Person A what they were doing Friday night and they said they were busy. You proceed to ask Person B to go on a date with you Friday and confirm only to have person A call later to say that they are suddenly free. Do NOT take the bait and cancel with Person B. Simply apologize to Person A and tell them you already made plans. Also, be sure that when you are on a date with one person, do not take calls from anyone or text anyone else as that is an infringement on your dates time. When dating casually, be sure to take time out for yourself as to not lose your own sanity.

How Many People Have You Dated at Once?

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Be an Equal Opportunist While Dating

Treat your dates equally. Don't allow one date to shade your perspective on the next date whether good or bad. By this I mean do not let something someone else did change how you treat someone else. Come in with an open mind for each new person. Also, try not to settle with one person before giving everyone else a chance. Lastly, please do not allow yourself to become so smitten with one person too quickly as you might be missing out on something better because you didn't allow room in your heart for anyone else.

And Then There Was One

Hopefully through dating casually you've found someone who embodies most of what you were looking for. If you both are on the same page, it may be time to seek an exclusive relationship with just that person. Yup, that means breaking it off with the other people you've been casually dating. Oh how we dread break ups. I can not pretend to be an expert at breaking up but I wouldn't leave you hanging. Hopefully the video helps!

Playing the field can be a fun experience if you let it be.Hopefully now you're prepared to play the field. Feel free to comment with any questions or concerns you have below.


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    • dashingscorpio profile image


      6 years ago from Chicago

      Voted up and useful!

      "Playing the field works best when you intend to have a serious relationship and you're just looking for "the right one." - Amen!

      I wrote a similar hub awhile back also explaining the process as being like a company who is seeking "the most qualified candidate" to fill a position.

      They have a "selection process" which may entail some phone interviews which may or may not lead to a face to face interview. If all goes well there will be a second or even third interview before a final decision is made. In the mean time they are also interviewing other "candidates" as well.

      The problem many people have with this approach is they want to become "exclusive" or "commit" to others BEFORE they get to know them. Some would even call this approach to dating: cheating.

      They fail to acknowledge that until there has been a discussion regarding being in an exclusive relationship with someone they should assume they are NOT in one! This is especially true of scenarios where people meet online.

      As long as someone's online dating profile remains active it means they're keeping their options open! They haven't met "the one"!

      Anyone who commits to the first person they meet without having gotten to know if they have the traits they want in a mate is making a mistake. You don't offer anyone a job until you believe they are qualified!


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