Ask Rob: Playing The Field

Dear Rob,

Is it OK to date more than one person at a time?  How many people can I safely date in DC at one time?

Short Answer?  Abso-friggin-lutley, and the number all depends on you.  I feel that first, it is common practice for people to be dating multiple people and it is only when people focus on antiquated rules of love, relationships and engagement that they start to feel guilty about it.

The negative issues that really come from dating multiple people actually stem from the “Am I a slut?”, “What about his feelings?”, “What would my friends/peers say?,” etc.  All of these things are constructed in your mind about what you expect others to think about you.   This is why I say the number of guys or girls you date is entirely up to you and how you view things.  Some people stick by their peers’ views (societal norms) a bit more while some do not.

I mean, when you see unimaginable bizarre love triangles, happy couples with huge age gaps, some of the ridiculous videos on the internet… pretty much anything is possible.  So you have one example where a person is dating multiple people and never picks one and maybe just enjoys getting free dinner–one of my co workers taught me that scam… she never really liked any of them but was always seeing multiple dudes and spending a lot of time fretting on which one was better.  I mean it was almost like a little kid laying out pieces of penny candy and trying to decide which order to devour the treats in.

Luckily for this segment, she also illustrates a problem coming from dating multiple people.  There could be a situation where the girl gets stuck between two (or in this girl’s case, 10) guys and then have a hard time deciding who to be with in the end.  Yes, there is a tiny percent of people who want a polyamoroous relationship or whatever new wave bullshit moniker you want to give a fake relationship.

So ladies, as you enter a multiple dating situation, know that there can be only one winner in the end.  And really, I’ve juggled a gaggle of ladies before but there is always one who totally trumps the rest.  A winning situation would be a lawyer friend of mine who was dating  a few people, then met a new guy who pushed her limits.  This had her dating 4 guys at once and she began getting nervous.  The thing is that after 3 weeks, the new guy started monopolizing all her time because he was great and they actually connected.

Okay now, those are all internal to the person who’s dating multiples and has made it okay in their brain to be doing this.  We have forgotten to include the case in which one of the dating candidates is unaware of the multiple dating and loses his or her shit and freaks out.  I personally talk about the nonexclusive agreement up front with people and don’t really talk about the other things I am doing with the multiple dating partners and I’m not constantly overlapping ladies…. just until I find one to stick with for a while.

Anyway, So what about the 3 girls and one is more in love with you than the rest and somehow she finds out that you have multiple dating relationships? Maybe the way you find this out is that you wake up in your bed the day she flys in from out of town and she is going through your cell while you were sleeping.  Maybe she finds the photos of the one girl that you deleted from your text messages and then resent to your email for safe keeping.  Maybe she found the Facebook post of the 3rd girl who had been visiting 1 day prior to the arrival of this girl.  Maybe this will be the first time that, as a man, a woman is going to give you a bloody lip.  Maybe you kick her out for being a crazy bitch, but maybe she’s the one you really want and you will beg her to stay and have passionate anger fueled fun times complete with smeared blood from your swollen lip making you question the next day if you are a human or a vampire.

But what about when the girls are dating multiples and angry dude comes over?  Crazy ex-boyfriends who bang on doors to come beat up the guy who is sleeping with his ex make me laugh.  Answering the door with a cell phone and a weapon and telling him you will call the police is an easy way of getting rid of that guy.  But once again, the crazies are on both sides and all you can do is control the internal thoughts and feelings that govern you.

Internal mental stability sets the stage to be completely ready for the external factors we can’t control.  So, date who you want when you want, but control that situation.


4 Comments Add yours

  1. Marie says:

    Rob, you start out this post by talking about it being ok to date more than one person at a time and that the objections to doing so are based on antiquated exceptions about dating, but then you go on to say that eventually, you have to choose one person. That strikes me as contradictory.

    1. This idea is contradictory. I think we will always arrive at similar conclusions, even if we start from and go different places along the way.

      If you have any more questions, Rob’s available to answer them!

  2. jkc says:

    what i find interesting is that Rob is seemingly able to sustain this steady group of quality women allegedly eager enough to date him even after receiving the knowledge that he’s concurrently dating several other people.

    “Girls, girls! You can ALL have me!”

  3. Thomas McDoubting says:

    While I found “Playing the Field” entertaining, I had one main problem with it: Rob. The author’s name suggests a male, but almost every aspect of this article suggests it was actually written by a female. As a male with an exact opposite personality type of Rob’s claimed type from a previous post, I understand there are differences among our species. But after reading this article, I’m convinced…Rob’s not a dude.

    If you read closely, Rob regularly speaks from a woman’s perspective. In the second paragraph, Rob discusses the sentiments “Am I a slut” and “What about his feelings?” What? When did we switch to the opposite gender, Rob? In the third paragraph, he leads with the “free dinner scam” scenario. That’s what the female gets out of it, where the discussion of what a guy gets (even if simply attention) for paying for a woman’s dinner? It’s as if he’s always starting from a female perspective and later imposing the male perspective on top of that.

    Maybe I’m getting bogged down on trivialities. But as I take a step back and try to get what Rob’s trying to say here, it just doesn’t add up. Rob clearly does two things that guys don’t do. First, he analyzes relationships… a lot. Men think about relationships, but I’ve never known one to analyze to the extent that Rob does. Conversely, all women I’ve known employ a great deal of relational analysis. Second, men don’t fantasize in the way Rob describes. I chuckled over the passionate, bloody, anger fueled fun times, but I’m sorry Rob, such exquisite level of fantasy can only be contrived by the opposite gender.

    In conclusion, my advice to Rob is to grow a pair and learn to play ball in the other field.

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