Dating Don’ts: How To Juggle Dating Multiple People At The Same Time

Dating Don'ts: How To Juggle Dating Multiple People At The Same Time

There comes a time in everybody’s dating career when your dance card suddenly becomes fuller than you know what to do with. One day, you’re swiping sullenly through Tinder bemoaning the lack of attractive, normal-seeming men that are possibly as tall as they say they are in their profiles, and the next, you find yourself drafting a spreadsheet to keep track of the nine dates that you have somehow booked for one week. Dating karma is like that. Like all things in life, your dating life will ebb and flow. Years of Sahara-like drought will give way to a summer full of eternal possibility, teeming with tapas dates and dinner dates and beach dates galore. One day, you’ll wake up in a daze, and find yourself with a bucket full of eligible, decent, good dudes, all clamoring for your attention.

“How could I possibly date two people, or even three people, when handling one person was too much?” you ask yourself as you scroll thru your texts one lazy Sunday. “How could it be that the universe is handing me such a Herculean task?”

Keep this in mind, dear reader. This embarrassment of riches is your prize for enduring countless shitty dates and rebuffing the advances of grody bros in I-banker loafers who are too drunk to see straight while you’re waiting in line for the bathroom. If you ever, ever feel bad about dating more than one person, remind yourself that if you were a dude, this behavior would be second nature.  This is unfamiliar territory, and it is perfectly natural to have questions. Let me assuage your concerns. Here are a few tips and tricks for juggling two people — or more! — at once.

Are there any hard and fast rules to follow?

The golden rule: Make sure they don’t know each other. I had a friend in college who happened to be dating two people at the same time for over a year. The deception in and of itself was bad enough, as she was forging deep connections with both, but the worst part? They were friends with each other and, inevitably, they found out. One day, she got home from class and found both of them sitting on the couch, waiting for her, and they were not happy. The fallout was dark. If you’re going to date two people, do your absolute best to make sure they don’t know each other, like, at all. If you find out early on that they do, abort mission.

When — or if — do I have to tell the people about each other?

There is an enduring instinct to treat people the way that we’d like to be treated. With dating, this rule sadly doesn’t always hold true. In short, you don’t have to do anything you don’t want to do, but especially if things don’t feel entirely serious just yet. It is not dishonest to keep each person in the dark because you’re weighing your options. You are a powerful and confident and fantastic person who deserves the very best, and sometimes it takes a minute to figure out what the very best is. If you’re casually seeing more than one person, keep that up until the balance tips in favor of one or the other. But until you have “the talk” about being exclusive, you don’t have to tell anyone anything.

Is having sex with multiple people something they have a right to specifically KNOW, especially if you’re using condoms?

This is where it gets trickier. Personally, if I’m having sex with somebody, I would prefer it that I was the only person they’re having sex with, but would love the freedom to be able to do whatever I wanted to do. Is this fair? No, not really, but as my mother always tells me, life isn’t fair. Regardless, the people you’re boning have somewhat of a right to know, but when and if you want to tell them is up to you. The instinct to let them know is natural, but I think if you’re being safe, and it’s not THAT serious with either party just yet, then you’re in the clear.

When does “dating multiple people” become “in my mind, I’m the leader of my own sex cult and I’m collecting followers”?

Who’s to say that dating multiple people isn’t a sex cult? Really, it’s all about your mindset. If your vagina is magic and keeps collecting various suitors, then your sex cult fantasy is your own personal truth. Keep doing what you’re doing, because it seems to be working.

What happens when one, or two, or three of the people are starting to catch feelings, and is leading up to The Talk, but you’re not ready for that?

You can’t have your cake and eat it, too. If you suspect that one of the people you’re seeing is starting to develop real, actionable feelings, and those feelings just aren’t there for you yet, it’s in your best interest and theirs to be honest. It’s perfectly okay to really like somebody, but not be ready to make the commitment that The Talk implies. Part of the allure of dating multiple people is that you’re trying things out to see what it is you really, truly want. It’s empowering and it’s necessary, and sometimes life just happens that way. The only shitty thing is the fact that you’ll probably have to let go of the one who wants to take it to the next level.

What if YOU are catching feelings for one of the people you’re dating, but you’re not sure if they’re there yet? Should you keep dating others until something more serious develops or go in for the kill on the one you want more with now and risk them ending it?

Life is nothing more than a series of risks, large and small, calculated and unplanned. It might be tempting to keep up the string of suitors for as long as you can handle it while pining away for the one you like the most, but I say go with what your heart wants. Take the risk to tell the one you like the most how you feel, and have confidence that it’ll work out however it’s supposed to. Any possible rejection you experience will be a blip on the radar, another lesson learned, but it shouldn’t slow your roll. Date! Be free! Trust that you will find another if this isn’t the one.

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