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Dear Culturalist: The Art of Dating Multiple People at Once

By Onya Ganja on July 11, 2018

Dear Culturalist: I have never dated more than one person at a time, but now I have totally fallen for someone who does not believe in monogamy. I know I need to start seeing other people, but I really don't even know how or what the rules should be. Can you help?

Are you sure you need to start dating other people? I am sure you don’t and that you actually have lots of options. For example, you could break up with the person. Just because you fell for someone does not mean they are the one for you or worth losing yourself and your happiness over.

You could also stay with them and just not see other people as well. If you have never dabbled in non-monogamy, you might as well try if you want to. Just don’t forget that no one, including Cupid, should force you into being one-half of an exclusive couple or into drifting in the sea of free love.

Try dating other people, but if that is not for you, you should not feel any shame. If you cannot be honest with your partner, you are doomed in the long run anyways. Unless both of you are gullible and excellent at lying, I guess… but that sounds shitty, doesn’t it?

Here are the top five ways to have an open relationship:

  1. Smoke so much weed that you don’t even remember you are dating someone, let alone five different people.
  1. Date only the people your partner is dating. With or without his or her knowledge.
  1. Go on twice as many dates as your partner. Out of spite.
  1. Only sleep with your partner’s friends. Out of spite.
  1. Hit on your partner’s friends in front of him or her. Out of spite.

If you think any of those suggestions are tempting, you have some feelings you need to chew and spit out. Except the first option, I think that is beyond totally acceptable, though some of my exes may or may not disagree.

The burden of working through your feelings shouldn’t be carried by your partner alone, but you need to be able to talk to them about it and work through it all. Swallowing some cannabinoids may help!

I have often seen people go wrong in the world of polyamory when they agree to something they are not emotionally or intellectually ready for—then they do passive aggressive things to their partner to deal with the hurt they feel. If you cannot talk about jealousy and work through it, you are likely not cut out for a polyamorous lifestyle, for now.

You have had a whole lifetime of monogamy training. Give yourself time to navigate your adventure in free-lovism and do not let someone else convince you their kind of polyamory is the only kind. The possibilities are endless. The only rules should be the ones you and your partner(s) decide on together.

A friend once told me that there are only two options when it comes to romance: monogamy or Pagan orgies. Good line, but mostly not true. There are a plethora of things in between to choose from, and if your partner cares about you truly, they will not force their kind of open relationship on you.

Monogamy has its advantages, and relationships are inherently complicated. I hate when non-monogamous people try to act like they are more evolved than someone who enjoys monogamy, or has only experienced monogamy to date. We are all a bunch of monkeys.

Once a “feminist” tried to convince me that he should be able to have sex with other people but that I needed to only hook up with him. So progressive. Also, ridiculous. That said, I have been in situations where I’m too busy or exhausted to date multiple people but would be thrilled to have other people keeping my sweetheart entertained.

How am I okay with my main squeeze getting high and low with other people? I love cats, and I love weed, I don’t have to choose between them because I love them both. I don’t love cats less because I love weed, and I don’t love weed less because I love cats. I feel the same is true for humans and their feelings about other humans. If someone really cares for you or me, they’ll stick around regardless of whomever else they meet.

Dating is a lot of work, or at least takes a lot of energy, so if you do a bunch of it, I am going to assume you find it fun. Just like smoking weed, why spend time with White Widow only? You could canoodle with White Widow flower, Lemon Skunk rosin, Nordle edible oil, Blue Dream pre-rolls or some mysterious chunk of hash from a friend you ran into at a chain restaurant.

If you try dating multiple people and simply find you do not enjoy violating this particular social norm, embrace that! It is good to step out of our comfort zones and explore what is outside them a little, but you are not a lesser human if you enjoy getting busy with only one person at a time.

Maybe you will blossom in the world of non-monogamy, though. If you do, you can date a bunch of people separately or find two or more people you want to be in a tripod, octagon or… whatever with. In my experience, the trick here is to ensure you all speak the same language. I mean that literally and not to encourage xenophobia. I find three-ways and five-ways where only two people speak the same language can get rather tricky.

For the record, probably best to ask your partner how to date multiple people at once instead of some random advice columnist who's always high and gives debatably serious guidance. Talk about all the possibilities together, see what works for you both, proceed with loving kindness and figure it out together. Or, excuse yourself for a moment and crawl out of their bathroom window, never to be seen or heard from again.

With drugs and with dating, it is better to slowly wade in than dive into the deep end. In other words, instead of running out into the world and having penetrative sex with the first person you see, you could consider going on a dinner date with someone and kissing them at the end of the night, or just smoking a joint while looking at the stars together and exploring your emotions.

Proceed in an unhurried way—maybe edibles would help? At least until you are comfortable or know how you feel. Just never forget to fuck sexual and romantic scripts and social norms. Date backwards while sleeping upside down like a bat if that is what you want. And if you are feeling like you might do something rash, such as inviting seven different romantic interests to the same event, deeply consider smoking a joint instead and asking yourself if it is really worth your time. Which is all we really have, and in uncertain amounts.


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