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Why You Should 'Challenge Your Guilt' Around Dating Multiple People

Dating around is totally fine. Here are some basic guidelines.

by Katie Moritz
July 19, 2019 | Love

The vast majority of us identify as monogamous. (One study estimated that 4 to 5 percent of people in the U.S. are poly.) But "casual dating" is kind of a monogamy gray zone — it's now completely the norm to meet people on apps, and with that shift has come some understanding that you must be swiping on and meeting up with others, too.

But you get a few dates in with someone and, depending on who you are and how you were raised and all kinds of variables, you might start feeling weird about the whole thing. Should you say something about seeing other people? Is that a given? What if you don't want to see other people? Is it too soon for that?

Whew. Something you were hoping would be fun and easy gets confusing real quick.

Take a deep breath. Every situation is different, but here are some guidelines to fall back on if you're stressing.

If you've been on less than three dates, press pause on your panic

At that point, "there is zero expectation that the interaction is exclusive," relationship consultant Adina Mahalli said.

Hold off on having a conversation about exclusivity until you've been on at least three dates.

That's when "it is appropriate to lay down what is going on, such as if there is exclusivity or if there are other people you are seeing," she said.

But the conversation doesn't need to be a tell-all. Don't make them feel weird by telling them details of other dates you've been on.

"Honesty is important, but oversharing is unnecessary. Merely explaining that you are still going on dates with other people, but nothing else is serious, is the respectful way to date multiple people."

Don't mix people up

Sound like something that could only happen in a sitcom? Nope, it happens in real life, too. The more people you're balancing, the harder it can be to keep all their information straight.

"Them knowing that you are dating other people is not an excuse for you to forget their names," said Celia Schweyer, dating expert at "Whenever you are with someone, make them feel that they have your full attention."

Staying organized and writing your dates in a planner (along with some biographical information) can help you keep everything straight, Mahalli said.

"When dating multiple people it is important to stay organized in order to not mix things up," she said. "Calling someone by the wrong name, overbooking and sending the wrong text are all issues that can occur when you are not organized."

Make sure you're emotionally present enough to be dating

There's a misconception that casual dating doesn't demand much from you emotionally. But it actually takes a lot to do it well and responsibly.

Illustration of couple having coffee together at a cafe. Dating Multiple People pbs rewire
At some point, you're going to have to break things off with people. Unless you've been seeing each other a long time, keep the conversation short and to the point.

Be prepared to have repeated and honest conversations about where your relationship stands.

"Meeting different people is already a challenge. Dating them is a different and much more complicated story," Schweyer said. "Should you decide to date multiple people, make sure that you can handle the situation. It also means that you know how to explain to them the real score and deal with their reactions as well."

Part of that is taking time for yourself. Make sure you're not seeing so many people every week that you have no routine or alone time.

"Start off just dating someone new once a week and progress to twice a week after a month or two, for example," said Paulette Sherman, psychologist, dating coach and author. "This way you can make time for other people and continue your own routine... so you maintain your life balance...

"Don’t develop a crush and spend (four out of seven) nights together after week two."

Journaling as you meet people is a good way to process your feelings and figure out what you want in a relationship, as well as a way to keep all of those potentials straight, she said.

Sex can mean what you want it to mean

For some people, sex is something significant that shouldn't be taken lightly. For others, it's something fun to do with somebody they're attracted to. And there's lots of nuance in between.

If you haven't had a talk about your relationship yet, it can be a good time to do it. It's definitely a good time to talk about whether you've been tested for sexually transmitted diseases.

"Sleeping with someone is a dating landmark, so you may want to have a talk at that point about monogamy or dating other people," dating expert April Masini said.

"If you don’t have that talk, assume they’re still dating other people. Sex isn’t a contract. And it doesn’t mean someone loves you or even has strong feelings for you."

Question your urge to get off the market

It can be really tempting to put all your eggs in one basket if you hit it off with someone. But that can be setting yourself up for hurt, either in the near or distant future.

Don't push for an exclusive relationship too early on. It might mean you're looking for security rather than the right person.

"The main reason why so many people are against dating multiple people is because they actually hate the whole getting-to-know-you dating process," relationship advice author Kevin Darné said.

"Oftentimes those who insist on dating one person at a time are the people that are hurt the most by ghosting or being stood up on dates because they behave as if they're in an exclusive relationship when they're not. Dating multiple people helps to lessen the pain of disappointment if someone does happen to vanish or reject you."

Remember, "in a world with over 7 billion people, rejection just means: Next!" Darné said.

Are you feeling guilty about dating multiple people?

"Challenge feelings of guilt or that voice that tells you that you may hurt your date’s feelings by seeing other people," Sherman said. "You can be honest and let all dates know you are taking things slowly before you close off your options."

Be mindful of how you're approaching the situation.

"If you’re dating other people, and nobody asks, you don’t have to fess up," Masini said. "You’re not doing anything wrong.

"If you find that you’re oversharing, then chances are you’re not comfortable dating multiple people. Reconsider this strategy for yourself."

Be realistic

Not everyone is "the one." Try to temper your expectations at the very start of a relationship. And be real about what you actually want out of dating.

"Remember that they may be dating multiple people — just like you are," Masini said. "If you’re not OK with dating someone who’s dating multiple people, reconsider your dating strategy."

Do you crush on everyone you go on a date with? Try to get to the root of that within yourself.

"Falling for someone you date is a common thing, but make sure you are capable of not falling for all of them," Schweyer said. "Set your boundaries and know how to control your emotions to avoid hurting yourself, and them."

Let 'em down easy

At some point, you're going to have to break things off with people. Don't feel like you need to lay out all the reasons why it's not working. Unless you've been seeing each other a long time, keep the conversation short and to the point.

"Honesty and communication is a great way to go about this, but... there is no need to make them feel bad about themselves by being brutally honest," Mahalli said.

There are (limited) situations when it's OK to ghost

Ending things with someone can be scary, but "anything after three dates deserves some form of an explanation," Mahalli said. Don't just pretend you never met each other and let the relationship fade into oblivion.

"While it is quite common to ghost these days, take the time to let them know that you aren’t planning on seeing them again," Schweyer said. "By doing so, you give them closure and they won’t waste their time with you.

"Be mature and extend the same courtesy you would want for yourself if it was the other way around."

Had that conversation and they still won't leave you alone? Then, and only then, it's OK to ghost them, Mahalli said.

"Ghosting is sometimes necessary when someone is overbearing and won’t take 'no' for an answer."

Katie Moritz
Katie Moritz was Rewire's senior editor from 2016-2020. She is a Pisces who enjoys thrift stores and pho. Follow her on Twitter @katecmoritz.
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