💬 Ask Ally: Does the awkwardness every go away when your partner is on a date?

An inclusive relationship advice column from couples coach Ally Iseman.

Welcome to my monthly inclusive relationship advice column Ask Ally, where I answer all of your burning questions about sex, love, dating, and all modern relationships!! These are real questions from real people like YOU.

This is part relationship advice, part sharing my own journey as a woman dating and relating non-monogamously. Think Carrie Bradshaw but without the Aiden vs. Mr. Big showdown, because, thanks to multipartner dynamics, I can be with both of them!

Paid subscribers of Passport 2 Pleasure can submit their own questions. I’ll select from those and answer anonymously for the benefit of all.

This month’s reader asks:

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Does the awkwardness ever go away for the partner who waits at home while the other is out?

First and foremost, I want you to know:

This is a common experience.

Whether you're just starting to explore relationship styles beyond the default setting or navigating established consensually non-monogamous dynamics.

That feeling you're describing? The "weirdness," the "awkwardness" when your partner is on a date? It's not only perfectly normal, but it's also a sign that you're engaging in the process of building relationships differently.

You're intentionally stepping off the well-worn path of the relationship escalator¹ and into territory that doesn't have an automatic GPS. So, give yourself some grace for feeling a little lost or clumsy sometimes.

We weren't given the tools and skills we need to build the relationships we want and deserve.

We're often taught one default model (one-size-fits-all monogamy) and left to figure everything else out on our own. When you choose a non-standard path, you're becoming the architect of your connection. And like any complex construction project, there are going to be moments that feel unfamiliar or, yes, awkward.

This feeling of awkwardness often stems from several places, all of which the practices of consensual non-monogamy teach us to navigate:

• Unspoken Assumptions

• Lack of Shared Language

• Insecurity and Jealousy

• Lack of Communication Skills

• Unclear or Unhonored Boundaries and Agreements

So, does the awkwardness ever go away?

Yes, the initial, surface-level awkwardness often does lessen significantly with practice and intentional effort.

As you and your partner develop self-awareness about your individual needs and triggers, improve your communication skills, learn to set and uphold clear boundaries and agreements, and build consistency in your words and actions, the unpredictable nature of navigating new dynamics decreases. This builds a secure container for your relationship, where you feel safer to explore, and inevitably, the "weirdness" starts to feel less... well, weird. You get more comfortable with the process, and it becomes a normal part of your relationship landscape.

However, relationships are always growing and changing, because so are we—no matter how many friends scrawled “NEVER CHANGE” in our high school yearbook.

Unexpected emotions will come up. New situations, different partners, or shifts in your own feelings can bring awkwardness or discomfort back, sometimes in new and challenging ways.

The goal isn't necessarily to eliminate discomfort entirely, but to expand your capacity to hold discomfort and learn that feeling uncomfortable is not the same thing as feeling unsafe. These two skills are not only crucial to developing secure relationships, but will impact and improve every area of your life.

But simply 'getting used to' the awkwardness, pushing through it, or just hoping it fades with time isn't building the secure, joyful, and truly thriving relationships you really want. It leaves you stuck in that "funk," constantly bracing for the weirdness or the fear that something might "blow up".

I know you.

You're looking for more than just tolerance or survival mode.

You desire confidence, ease, and the ability to transform these moments of discomfort into powerful opportunities for deeper connection, personal growth, and shared joy.

The truly limitless relationships—the ones built on conscious choice and intentional design—require moving beyond mere management of discomfort. They require specific tools and skills to turn potential friction into stronger bonds. They require...

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Are you tired of just 'managing' the awkwardness and ready to learn how to confidently build relationships that feel both secure and truly limitless?

This is where the real transformation happens.

Unlock my full answer and get access to the specific, actionable strategies and deeper insights required to move beyond just coping. Turn discomfort into a catalyst for growth, strengthen your connection through radical vulnerability, and master the art of intentional relationship design. Get the tools you need to open up without breaking up…