Dating Multiple People – The Attachment Style Perspective

Picture this. It’s late 2021. You’re out there reconnecting with the world, the people in it, and all those possibilities. After way too much time socially distanced, you and a lot of other people are hungry for conversation and closeness.

One solution: dating multiple people (safely, obviously!)

These days, dating more than one person at one time is not unusual. In fact, I am willing to bet the trend will grow even bigger.

But how does dating multiple people actually sit with you? What would that really look like? That’s something harder to nail down. Especially if you’re unaware of your attachment style.

In this article, we’ll dig into what dating more than one person looks like, but we’ll do it through the lens of your attachment style. This will help focus your options, minimize discomfort, and optimize your dating strategy.

We’ll quickly break down all 4 attachment styles and some ways they manifest. Then, I’ll lay down specific advice for what to expect—and how to process—dating multiple people.

What Is An “Attachment Style”?

A person’s attachment style develops throughout childhood. It’s impacted the most by your parents or primary caregiver.

It’s something that affects every relationship you have as an adult—on every level—but in your romantic life, it affects everything from the kind of sex you crave to the way you break up with someone.

There are 4 main kinds, as categorized by British psychologist John Bowlby and later, the amazing Mary Ainsworth.

Each style is also drawn to its opposite. This means that someone with an anxious attachment style will often find themselves attracted to people with an avoidant attachment.  Also known as the anxious-avoidant trap!

Now, let’s dig deeper.

Anxious Attachment

Someone with an anxious attachment style often finds it hard to trust people, especially someone they’re vulnerable to—like romantic partners. This person craves affirmation, security, and validation from their partner because they’re often worried (on some level) their partner does not love them.

They might also feel dating someone with an attachment style too different from theirs is boring. Someone with a secure attachment style might even come across as extra suspicious!


If this style resonates with you, multiple dates may be fine. But having multiple partners will probably create a lot of stress.

The lack of exclusivity can lead to feeling insecure or unstable in the relationship. On some level, you may be worried a partner is giving the same validation and affection to other people.

If you’re going to try it, I encourage you to make sure you’re developing ways of affirming yourself. Otherwise, the rush to seek out more and more people for more and more validation can lead to you picking people entirely wrong for you.

Avoidant Attachment

Similar to the anxious type, this style tends to distrust others. But instead of compensating by getting closer, avoidant attachment types depend on distance for a sense of safety.

People with this style might find it hard to emotionally connect with others. They might also find it hard to express their own needs in a relationship.

On the surface, this seems like cool and easy independence. But studies have shown there’s a ton of internal stress. Avoidant attached people commonly dwell on whatever issues there are in a relationship, but have trouble opening up about them.

Or, they will wind up fixating on some minor issue, which is then used to justify a breakup or emotional distance.

Avoidants will often find secure attachment styles too stable for their taste, even though that stability lets them keep their autonomy. Anxious attachers… Let’s just say it’s a volatile mix!


On one level, the avoidant attachment style has some advantages when dating multiple people. Men and women with this style prioritize freedom, autonomy, and options. That’s their way of protecting themselves from hurt.

This means they have little trouble ending a relationship that doesn’t sit right or doesn’t match their personality.

That being said, if this is your kind of attachment, it’s a good idea to balance sovereignty and intimacy in your relationships. Additionally, learning how to express your emotional and physical needs will be a huge benefit.

 Disorganized Attachment

Children who grew up learning this style can have a uniquely difficult time as adults. Disorganized attachment style can develop out of confusing or inconsistent parental reactions to the child’s stress levels, or enduring/witnessing abuse and trauma.

A person with disorganized attachment craves love, affection, and intimacy but is terrified of those things at the same time. In dating, this manifests most often as contradictory behavior—one minute, there will be a hard boundary around quality time. The next, avoidance.

This is because people with disorganized attachment see rejection, trauma, or pain as unavoidable. They will sabotage relationships because they unconsciously assume things will fall apart anyway.


Real talk: If you feel this is your style, you will benefit most from learning how to identify and verbalize the feelings you’re going through. Your trauma deserves to be healed. You deserve a life controlled by you, not the stories and events of your past.

I recommend placing extra emphasis on healthy dating habits. You can date multiple people of course, but be mindful. Prioritize people with secure attachment, since their stability and support will help you feel safe.

Secure Attachment

Despite what you might have endured on dating apps, the truth is that most people out there learned a secure attachment style. There’s a bunch of possibilities a secure style can bring to dating.

The secure attachment person will be pretty selective with partners. They are flexible, self-aware, and will readily share their feelings. They trust their instincts, and stick to the rules and boundaries they set, but are open to someone else providing input (or healthy criticism).


A person with secure attachment style can generally handle dating multiple people. Nevertheless, stay strongly aware of your boundaries and goals, and don’t be afraid to lay them on the table.

Wait…Am I Stuck With My Attachment Style Forever?

Nope! Let me put it bluntly: no one is an unchangeable rock. Anyone can move towards an attachment style that fulfills them and gets the results they want.

Here’s the thing: your attachment style is a part of you, not the whole thing. You always carry the potential to show up to dates (or a job interview or that hard conversation with your mother) as someone who is secure, learning, growing, and changing.

But in order to change, you need time and research—and to crush the self-care game. But that’s the beauty of life, right? The more we learn and care about ourselves, the more we can learn, bond with, and care for each other!

Advice For Every Style

There are a few ideas any attachment style can apply to dating. When it comes to dating multiple people, every human being should have these tools in their kit.

  • The 3 W’s: In any situation involving other people, the 3 W’s are something that really help connect you to your instincts and identify what to do next: What am I feeling in my body? Where is it coming from? What do I need?
  • Coaching and/or Therapy: Take charge of your mental health! A reliable coach or therapist will help you identify and heal old wounds, cultivate a secure sense of self, and create healthy relationships that serve instead of sabotage.
  • Re-Examine Your Labels: The human experience is complex! It doesn’t always fit a category or label, and it is changing all the time. You might find, as you grow, your style changes. That doesn’t mean the label was wrong—all it means is that you’re growing.
  • It Is Ok To Pause: One question I often get from clients is how often they should be going on dates. To be honest, there’s no single rule about this. Trust your instincts—if they’re saying “I need a break from dating”, take a break.
  • Have Intentions, Not Expectations: The advantages of this reframe are huge. One depends on you, the other depends on things and people outside of your control.
  • Create Healthy Boundaries: Give yourself some solid rules and dealbreakers. This screens people who might abuse your independence, and it will ultimately save you time.

If this content resonates with you, try out our weekly support group where we dive deeper into attachment styles, The Enneagram, and how to create your ideal relationship.  Apply now by clicking here!

Leave a Reply

%d bloggers like this:
search previous next tag category expand menu location phone mail time cart zoom edit close