Ever wondered how to plan a threesome without the drama? It's easier than you think... but it takes communication, trust, and a little bit of flair.
I’m going to take you step-by-step through the important conversation that stops the fantasy from becoming a nightmare, and how to find that elusive “Third.”
Keep reading/watching for the ultimate guide to keeping it fun, healthy, and scandal-free. Learn how to turn your fantasies into reality—without the awkward aftermath!
Hi! I’m Ally Iseman! I’m a relationship coach and I want you to have the tools and skills you need to build the relationships you want and deserve. I share all the lessons I’ve learned the hard way, so you don’t have to!
Threesomes—so hot in theory, so awkward in reality… but with a little planning, you can turn a ‘never again’ into a ‘best night ever.’
By the end of this post, you’ll know exactly how to plan a fun, ethical, and drama-free threesome—whether you’re monogamous, polyamorous, or…just curious.
Fantasy vs. Reality
There are a lot of common misconceptions when it comes to threesomes. Some of the greatest hits are:
It’s just spontaneous fun (generally not).
Everyone will be equally into it (not always true).
No one will catch feelings or feel left out (hello, reality check!).
The truth: A great threesome takes the 3 C’s of communication, consent, and compatibility—not just attraction.
So whether you’re three singles or a couple looking for a new friend, you’re going to want to read this entire post to make sure your first threesome doesn’t become your last!
Step one?—before you even start swiping through any of the apps or texting that ‘cool’ friend, let’s talk about why you actually want this in the first place…
Step 1: The Pre-Game Talk
Before you start playing, it’s important to discuss the game plan. That means walking through the Before, During, and After PRIOR the big day. No team has ever won a championship without running through every possible scenario first, and you’re about to enter the Sex Superbowl! [Please don’t make me do any more sport references.]
BEFORE
Be honest with yourselves and each other. Are you doing this for the right reasons?
Trying to “save a relationship”? [Bad Idea]
Exploring fantasies to spice things up? [Better Idea]
Looking to add novelty and deeper connection in an already secure dynamic? [Best Idea]
Educate yourselves. Explore books, articles, and podcasts. Watch some ethical porn featuring threesomes. Schedule a good chunk of uninterrupted time to talk about it from the perspective of how you want your partner to feel during and after the conversation. Planning some non-sexual intimate time–like a walk or sharing over tea–can be a connected and compassionate setting in which to talk about it.
The Poly vs. Monogamous Approach
For my monogamous couples, ask yourselves:
Is this a one-time thing or are you opening a door to something potentially ongoing?
What are you hoping to get out of this individually and together?
Monogamous couples often need extra clarity to avoid unspoken jealousy or misunderstandings. It might be worth creating a Reconnection Ritual to reestablish your special connection afterwards. This can be as simple as a shared bath or revisiting a location significant to your relationship.
And for my non-monogamous couples:
How does this fit into your existing agreements?
Polyamorous people might have more experience setting boundaries, but it’s still important to check in—every dynamic is different and boundaries can change at any time.
If you’re in a relationship, regardless of the style, are both partners equally excited—or is one just going along with it?
The Biggest Red Flag?
If one person seems hesitant, unsure, or only doing it for their partner—it’s time to pause and take a step back. No fantasy is worth sacrificing trust and emotional safety.
My solo participants, my thirds, my beautiful unicorns…
Are you looking to join an established couple? If so, what’s in it for you?
This is just as much your experience as it is theirs. So make sure you’ve thought about your own DIBs—Desires, Intentions, and Boundaries—so you’re not just showing up as a tool for their fantasy fulfilment, unless that’s what you’re into. No shade here. The point is to think about it and make a conscious choice.
Something else to look at is whether you’re most excited to connect with the couple together or only one of the duo in particular. Symbiosexuality is the attraction to an already existing dynamic, and can be really juicy, but it’s also totally okay if you're only interested in connecting with one of the partners.
The most important thing is to be upfront about either one from the beginning.
DURING
Why Expectations Matter
The biggest mistake people make? Thinking that a threesome will just ‘flow naturally.’
Spoiler Alert: It won’t.
Everyone involved has different desires, comfort levels, and boundaries. The only way to avoid miscommunication, hurt feelings, or a total vibe kill is to talk it all through—before clothes start coming off.
Get on the same page by discussing your DIBs:
Desires: What are you hoping to experience?
Intentions: How do you want to feel?
Boundaries: Create a Yes, No, Maybe List
What do you definitely want to try?
What are the no-go zones?
Are specific acts off-limits? (Example: No kissing, no one-on-one time, no PIV, etc.)
Do you want a ‘safe word’ or non-verbal gesture you can use if things feel off?
Release any idea of perfection or doing it “right.” The richest intimacy can come from those shared awkward moments that arise naturally in a new experience. No one needs to feel like a performer here.
AFTER
With the right preparation, you can keep aftercare from becoming aftermath.
What happens after?
Who is calling or texting or getting together with who—when and how often?
If feelings come up, how will you handle them?
Want a deeper dive? Check out my Jealousy Toolkit to keep your connections strong before and after exploring threesomes.
Okay, so you’ve set expectations and you’re both on the same page. Now comes the fun part—finding the right third. But trust me, there are some mistakes you really don’t want to make here…
Step Two: Finding the Right Plus One
You’ve heard the old saying, “Keep your friends close, but your fuck buddies closer.” Or something like that. This is where a lot of people go wrong.
“Let’s just ask my best friend!”
Yeah… don’t do that.
Inviting someone who is already too emotionally entangled can lead to complex jealousy. Yet someone too random can lead to other types of discomfort.
A quick note on terminology, because I’m a word nerd.
You might hear the term Unicorn or Third when a couple is looking to add to their dynamic. This treats the couple as a unit and excludes the other person as outside of their dynamic. It is an example of something known as ‘Couple Privilege’ and it is important to be aware of.
There’s nothing wrong here, it just means you’ve already spent time building your connection and may naturally have some shared language, behaviours, and practices between you. Reflect on how this could impact the person you’re inviting into your dynamic and how you want them to feel about their experience with you.
While a threesome can just as easily not include a pre-existing couple, for the purposes of brevity in this article, I am using the term third.
So where are the best places to find the right Third?
Dating apps geared towards inclusive relationship styles and sexual exploration
Play parties or sex-positive lifestyle events
Online communities for non-monogamous folks
The Golden Rule of Thirds? Invite someone who’s just as enthusiastically into it as you both are, and isn’t just agreeing to please you.
Did you pick the wrong third for your first threesome? Spill the tea!
Avoiding Common Pitfalls
So many couples make so many mistakes. But that’s not you. You’re savvy and clever and reading this first. So let’s learn how to avoid them!
DO: Use dating apps designed for non-monogamy and sexual exploration. There’s actually more to choose from than you might think!
DON’T: Spring it on a friend at a party (“So… we were wondering…”). Awkward.
DO: Be upfront and transparent in your approach.
DON’T: Treat the third like an accessory or assume they have zero preferences.
The Unicorn Trap
Many couples go looking for a ‘unicorn’—a magical and elusive creature: the bisexual woman who has no emotional or sexual needs of her own and exists solely to enhance their relationship.
Fun Fuck Fact: Most people don’t enjoy feeling like a sex toy with a pulse.
Instead, approach potential partners with respect, curiosity, and clear communication. And since you’re already ahead of the curve by reading this, you’re prepared to…
Avoid These Three Common Mistakes:
Overhyping & Underdelivering: Flirting for weeks, building tension… then ghosting because one partner got cold feet.
Ignoring the Third’s Experience: Your couple dynamic is great, but what about their comfort and desires? They’re a whole and complete person too.
Skipping the Vibe Check: Just because someone is hot doesn’t mean they’re the right fit. Chemistry between all three people matters.
Pro Tip: A group chat before meeting IRL or a low pressure get together before the big event can help gauge comfort levels and avoid awkward surprises.
Alright, so you’ve found the perfect third—exciting! But now, let’s talk about what happens during the threesome… because if you don’t handle this part right, things can go south real fast.
Step Three: Rules of Engagement
You’ve talked about your own DIBs, but as we discussed, the third party is a whole ass person too, which means they have their own Yeses, Nos, and Maybes. Have the awkward but oh-so-necessary conversations. Go over all the details. Leave no sexy stone unturned.
Here’s a birds eye view of some basics, but by all means, feel free to add your own.
Consent, boundaries, and expectations are HOT.
What’s on the table (and what’s not)? Discuss everyone’s DIBs: Desires, Intentions, and Boundaries.
Safer Sex Talk. Condoms, STI testing, and birth control, oh my! What’s your exposure plan? Are you all on the same page about accidental pregnancy?
Emotional Check-in. What happens after? Who needs what kind of aftercare from who?
Follow Up. Is this a one-time thing or a recurring dynamic?
Since you’re a hot little smartypants reading this whole article, can you guess some of the biggest boundary fails I see with couples?
One partner getting left out.
Not having a “check-in” plan during or after the experience.
Leaving the third person unsatisfied.
Pushing past relationship agreements, aka shared boundaries.
Pro tip: Use a traffic light system (Green = all good, Yellow = it’s time to check-in, and Red = stop immediately).
Location, location, location!
When it comes to threesomes, especially as a couple and especially for your first time, choose neutral ground like a hotel or local NOMAD home swap over your shared bed at home…unless of course you like emotional landmines.
Determine who’s in charge of what with clear expectations and responsibilities beforehand.
Music? Drinks? Vibes?
Who’s supplying what contraception?
What if any toys will be available and who’s bringing them?
Once all of these important details have been laid out clearly between all parties involved, then and only then is the groundwork laid for things to unfold naturally. With this level of sexy communication and consent, there won’t be any undue pressure.
You’ll be prepared to read each other’s body language as clearly as spoken words so you won’t need to over-talk during the event. Though taking periodic mini breaks to check in is always the vibe. A quick ‘you good?’ mid-threesome goes a long way.
Ongoing consent check-ins are an art form you’re going to master in the next section.
💗 Please consider RESTACKING if you enjoyed this post💗
The Main Event
Now that you’ve each done all that sexy prep work—think of it like foreplay—let’s talk about how to make the experience itself fun, and not awkward, for all.
The Golden Rule of Threesomes?
Everyone should feel included, respected, and prioritized.
If one person feels like a spectator or an afterthought, the vibe is instantly ruined. A great threesome isn’t just about sex—it’s about connection, comfort, and pleasure for everyone.
If you want to understand how to do that, make sure to subscribe and stay tuned for next week’s post where we’ll break down the play-by-play of the main event, how to keep aftercare from becoming a dramatic aftermath, and what to do if you want to make this an ongoing thing.
Three’s A Crowd(pleaser): Enjoying A Drama-Free Threesome
You’ve always been curious to try, but are drama-free threesomes actually possible? This video is your ultimate guide to group fun without the aftermath. Plus, I’ll tell you how to make threesomes a …
Or maybe this opened a door into the possibility of opening up your relationship in a bigger way to explore consensual non-monogamy. I’ve got everything you need to open up without breaking up in my comprehensive course ENM 101. Check it out!
If you’re ready to open up, the first step is just a click away.
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