If you have several exes (or prospective partners) lingering, you may reason that your dating pool investment has the potential to be rewarded if one finally coughs up a relationship. The idea is that you’re spreading and limiting your risk by not cutting anyone loose or making a choice and choosing one.

A part of you might wonder, Well, what if I get it wrong? What if I choose this person and they turn out to be emotionally unavailable or shady? Then I have no one.

So keeping in touch with several exes or corresponding with or dating several prospective partners at a time keeps your options open while safeguarding you against being hurt. They’re your fallbacks, a safety net.

Depending on what you want, dating several people might be blocking intimacy. It’s also holding on to people for the wrong reasons. Like putting them on layaway just in case.

If you’re not looking for a relationship or you want to be in an open relationship, though, crack on. Dating several people at a time while being conscious, aware, present and respectful is so different from doing it with a hidden agenda. There’s no avoidance and you’re mindful of self-deception.

Whatever you’re doing, it’s about knowing your ‘why’. Intentions dictate outcomes.

When you’re authentic and so aware of your ‘why’, you won’t advance your self-interest while claiming it’s mutual. The other parties are in on what you’re doing, so they too can make emotionally responsible decisions. They’re not fallbacks, safety nets and rainy-day options if someone else doesn’t pan out. It’s not you dating several people while they think they’re the ‘only one’. You’re not playing them off against each other or pretending one is more special. There isn’t a fearful, controlling, let-me-keep-one-foot-in-the-door-just-in-case energy.

When, however, you want a relationship but you’re also afraid of one at the same time, you gravitate to people who make it easier for you to be in your conflicted place. You might treat people like a means to an end. Next thing, you’ve got your relationship hedge fund of people with limited or even non-existent capacity for a committed relationship. Much as that can initially feel exciting or flattering to have several people on the go, that will wane. When none of them chases you down or commits, it will feel like you’re ‘not enough’. It will feel like market research that proved something negative about you.

So sure, date several people at once, keep in touch with exes and whatnot, but stay on top of your ‘why’. It’s bad enough losing yourself with one person, never mind several!

Are you ready to stop silencing and hiding yourself in an attempt to ‘please’ or protect yourself from others? My book, The Joy of Saying No: A Simple Plan to Stop People Pleasing, Reclaim Boundaries, and Say Yes to the Life You Want (Harper Horizon), is out now.

The Joy of Saying No by Natalie Lue book cover. Subtitle: A simple plan to stop people pleasing, reclaim boundaries, and say yes to the life you want.
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