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Why Awkwardness Is the Secret to Better Connections in the Swinger Lifestyle

Writer's picture: JakeJake

We all have visions of how we want things to go, especially when it comes to sex in the swinger lifestyle. But if there’s one thing seasoned swingers know, it’s that awkward moments are inevitable, no matter how much experience you have. Whether you’re a newcomer or a veteran, things don’t always go as planned—and that’s okay! Those awkward, unexpected moments are often where the most growth and connection happen.


It’s important to understand that awkwardness feels uncomfortable because it makes us feel vulnerable. As humans, we generally try to avoid feeling vulnerable. However, vulnerability can be freeing as it allows us to let go of pretense and the pressure to appear perfect, fostering deeper connections and authentic relationships. When we embrace our vulnerability, we relieve ourselves of the emotional burden of hiding our true feelings and accept that we can't control how others will react. This brings a sense of liberation.

 

Vulnerability also builds trust and intimacy, encourages others to open up, and promotes personal growth by pushing us out of our comfort zones. Through this openness, we learn to accept ourselves, flaws and all, breaking free from the unrealistic standards we often impose on ourselves. Ultimately, vulnerability leads to greater authenticity, connection, and inner peace.


Let’s talk about why embracing the awkwardness in the swinging lifestyle can be a powerful tool for deepening both your sexual and emotional experiences.


Why Awkward Moments Are Part of the Package

When you’re engaging in intimate acts with new partners, trying out fantasies, or navigating complex group dynamics, there’s no way around it—things can get clumsy, confusing, or downright awkward.

1950s illustration of woman spilling ink
Sometimes things get messy

Once, Abby and I were in a hotel room with another couple and didn’t realize the guy had opened a bottle of lube without securing the lid tightly. So, mid-play, someone’s foot accidentally knocked over the bottle. What a mess! Picture four naked adults, entirely in the moment with each other, suddenly stopping to stare at the pool of lube forming on the bed. The subsequent clean-up—because we’re responsible adults, after all—was annoying but also funny and memorable.


The point is stuff happens. Whether it’s someone not realizing they’ve placed an arm in an awkward position or there’s a pause that turns into nervous giggling, know that it’s all part of the human experience. Like anything else, Swinging is not immune to the little hiccups that make life real.


Even those who’ve been living the swinger lifestyle for years still encounter awkward moments, whether physical mishaps, communication blunders, or unexpected emotional reactions. However, those awkward moments often lead to more authentic connections, personal growth, and fun memories. Here are five things we’ve learned about awkward moments and how to embrace them:


1. Awkwardness Builds Authentic Connection

When things don’t go according to plan, we must drop our guard. That moment of vulnerability—whether it's fumbling with a new position, accidentally bumping heads, or a nervous laugh mid-scene—reminds us that we’re all human. These moments create authenticity, which leads to deeper connections, not only with your partner but with anyone you’re playing with.


Awkwardness brings down the polished, “perfect” image we might think we need to uphold. By embracing these moments, you foster real intimacy and show others (and yourself) that it’s okay to be imperfect.A good laugh can diffuse tension and make everyone feel more comfortable moving forward.


Tip: When something awkward happens, try using humor to lighten the mood. A shared laugh can turn a potentially embarrassing situation into a bonding moment that eases everyone’s nerves.


2. Learning Through the Stumbles

Let’s be honest: nobody is great at something the first time they try it. Whether it’s your first time experimenting with a threesome, integrating kink, or exploring a new type of group dynamic, mistakes or uncomfortable moments are just part of the learning curve.


Instead of seeing awkwardness as a failure, consider it a valuable opportunity for growth. Every time you try something new, you learn more about yourself, your desires, and how you connect with others. Did a new position turn out to be more complicated than expected? Did a fantasy sound better in your head than in reality? That’s okay—now you know! Each moment of uncertainty is a stepping stone toward becoming more comfortable with yourself and your experiences.


Tip: Use any awkwardness as a conversation starter. Abby and I often lean into it to break the ice and get people to relax and laugh. Discuss what worked and what didn’t in a light-hearted way. You’ll often find that everyone involved felt similarly and appreciates the opportunity to tweak things for next time.


3. Awkwardness Sparks Playfulness and Creativity

Awkward moments are often unpredictable, and that unpredictability can add to the excitement. They force you to think on your feet and improvise. When a plan doesn't go smoothly, there's room to get creative and experiment with new ideas, positions, or dynamics.


For example, getting into a sexual position with two or three others can feel logistically complicated—but don’t be afraid to acknowledge this out loud. A joke can go a long way to make trying different configurations, switching roles, or introducing a new toy easier. In a group play scenario, if the original plan gets interrupted, go with the flow and explore whatever direction the energy naturally takes. Swinging is inherently playful, and when things get awkward, there’s often an opportunity to turn that energy into something fun and spontaneous.


Tip: When something unexpected happens, don’t rush to fix it. Take a breath, regroup, and see how you can turn the situation into something even more enjoyable than you originally planned.


4. Laughing at Yourself (and With Others)

One of the best ways to embrace awkward moments is to learn how to laugh at yourself. When you let go of the need to appear flawless or smooth, you open the door to more joy and playfulness in your swinging experiences. A good sense of humor can diffuse tension and help you, your partner, and other participants stay relaxed and focused on having fun, rather than being perfect.


A few years ago, Abby and I were with a couple new to the lifestyle. While the four of us were playing, Abby and the other woman started kissing and caressing each other. It was her first time engaging in same-sex play, and we could tell she was excited but nervous. The guy and I watched, enjoying the moment, when suddenly he jumped up, grabbed a double-sided dildo from his bag, and tried to introduce it into the mix. Clearly, he had this fantasy all planned out in his head, but it wasn’t quite the right time. The women awkwardly fumbled with it for a moment, and the energy fizzled. Instead of letting the moment die, the guy cracked a joke about his grand plan, and we all laughed. What could’ve been an awkward moment became a funny memory.


Tip: Don’t take things too seriously! The more relaxed you are, the easier it is for others to follow your lead. A good laugh can make everyone feel more comfortable.


5. Embracing the Unexpected Enhances the Swinger Lifestyle

Swinging is about exploring pleasure in its many forms, and sometimes, that pleasure comes from the unexpected. When you let go of rigid expectations and embrace whatever unfolds, you’re more likely to enjoy the experience. The pressure to have everything go “perfectly” can rob you of the spontaneous fun swinging offers.


Instead of trying to control every element, go into experiences with an open mind. Be prepared to laugh, adapt, and enjoy the ride—whatever that may look like. You might even find that what you thought would be awkward turns into a new favorite moment or fantasy.


Abby and I were once with another couple—her with the guy, me with the other girl, both girls in the missionary position. As we know, this position lends itself to significant thrusting, so understandably, the bed was rocking hard. Suddenly, mid-play, we heard a bang, and one corner of the mattress dropped—it had presumably fallen off the frame. Both the guy and I abruptly stopped, and everyone burst into laughter. What could have been a mood killer turned into a shared moment of hilarity, making the evening even more memorable.


Tip: Prepare to be flexible. If you approach each encounter as a unique experience rather than one bound by specific bucket list items, you’ll free yourself (and your partners) to truly enjoy the moment.


Conclusion: Awkwardness is Part of the Fun of Swinging

In the swinging lifestyle, awkward moments are inevitable—and that’s a good thing. Authentic connection, growth, and creativity emerge in these unscripted, unpredictable moments. They allow you to laugh, learn, and play—all essential ingredients to making swinging fun and fulfilling.


So, next time you stumble, giggle, or find yourself in an unexpected situation, don’t stress. Embrace the awkwardness. It’s all part of the journey, and more often than not, those moments will be the ones you and your partners remember most fondly.

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