This Is The Key To Successfully Dating Multiple People At Once

Here's how to make sure nobody gets hurt (including yourself).
Willie B. Thomas via Getty Images

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The world of dating is complicated. How do you know if someone really likes you? When do you know when it’s time to meet their friends? Is it okay to ever double text? Getting to know someone can be overwhelming, now imagine trying to do this with several people.

Some people like to date one person at a time, whilst others don’t want to keep all their eggs in one basket. This week’s reader, Pauline, is in the latter camp – but she’s not finding it easy.

She writes in saying: “I’ve started dating two people and I really like both of them. I want to know how you can successfully date several people at the same time.”

How can you date multiple people without hurting anyone (including yourself) in the process? Counselling Directory member James Eve has some advice.

How can we decide who we should continue to pursue if we’re dating multiple people?

Obviously polyamory is a (very legitimate) option for those it suits. But those looking for longterm monogamous love will need to make a decision on who they most see themselves with at some point.

“How you decide on this depends on what you would like just beyond dating. This could mean a committed relationship, cohabiting, marriage, children or none of these things,” Eve says.

“But asking this sort of question may help you decide what comes next for you. Can we like people equally or do we have different preferences based on what we want (or don’t want) from the next phase of a relationship?”

Choosing or deciding on a person can bring up feelings of conflict, adds Eve, because “to choose is to lose the possibility of something else”.

“Having choice can also stave off feelings of vulnerability if we are deciding to invest in multiple people and hedge our bets,” he says. “Having any sort of real and intimate relationship does require an investment of our time, energy and resources: essentially an investment of ourselves into someone else.”

When should we cut off other people we’re dating and focus on the person we like the most?

You’ll need to make a choice based on your own feelings and what you’d like to come next.

“As difficult as it may be, it’s worth talking openly and honestly to the person you have decided on,” says Eve. “Do they feel the same? Will you be exclusive? Of course a next step common in today’s dating rituals is ‘shall we delete the apps?’”

In order to progress and move forward, he recommends knowing where you both stand, being transparent and avoiding playing games. At this point, you should also stop stringing the other person along.

Deciding not to progress with a person is a “very natural part of the dating game for everyone”, he adds. Just make sure you break off ties sensitively.

“Of course, this also involves the other person liking / wanting the same (why this is all so complicated!). But perhaps those people you choose to ‘cut off’ deserve a conversation and some honesty about you choosing to end things.”

How can we date multiple people without hurting other people’s feelings?

“There is nothing wrong with dating and seeing different people. The key word here is ‘feelings’, which may develop if there is an investment or a connection, usually over a period of time,” says Eve.

“There are no rules here, and hurt feelings are sometimes unavoidable.

“Perhaps you enjoy dating multiple people and this is what you’d like to continue doing? Whether you tell them and how you broach this sometimes sensitive topic is your own decision. Whether they react with hurt / disappointment or pure indifference is their decision.”

Love Stuck is for those who’ve hit a romantic wall, whether you’re single or have been coupled up for decades. With the help of trained sex and relationship therapists, HuffPost UK will help answer your dilemmas. Submit a question here.

Rebecca Zisser/HuffPost UK