How to Be a Great Single Gentleman in the Swinger Lifestyle

Showing up is easy. Becoming the single gentleman people actually want around often takes a little more work.

Single gentlemen sometimes get a bad rap in the lifestyle. Some of it isn't deserved.

Some single gentlemen... well... we've met that “gentleman” too.

The great single gentlemen aren't necessarily the youngest, best-looking, richest, or the gentleman whose profile claims he's “very well endowed.”

Isn't it interesting that no single gentleman ever describes himself as adequately equipped and reasonably competent?

We're going to tell you how to succeed in the swinger lifestyle even if you don't have a ten-inch anaconda between your legs.

Because despite what you may have been led to believe... your penis isn't your résumé.

Hugh and Judy enjoying wine together
The recurring rule on this page: keep both people involved.

Be Social Without Expecting Sex

Wow, we know... this is going to be hard, and not the good kind of hard.

Go to meet-and-greets, parties, trips and events because you enjoy people. Become someone others know and like... not the gentleman circling the room looking for... well, a wet hole.

Believe it or not, couples can smell this attitude... and you might reek.

Clean Up Before You Show Up

When you finally meet a couple you like... hopefully they are smiling at you.

Take a bath just before going. Do not bathe in cologne. Brush your teeth and bring some type of mouth conditioner with you.

Do not rinse with Fireball and think that is enough.

Wear nice clothes. No, we are not talking about $100 shirts, but something nicer than a T-shirt... unless that is the theme.

Trim your nails... all of them. You never know if a lady might be into feet. We are not kidding.

Congratulations. They still like you. Now try not to ruin it.

Make Friends With the Male Partner

This one is very important. For the first 30 minutes, maybe more, the conversation should be mostly to him, with questions about what she likes mixed in with normal everyday conversation.

Yes, you have to figure this out on your own. Judy can't be on the phone listening to your conversation and giving you lead-ins.

If he leans into her for her to answer, go back to him for a follow-up. “Are you going to just watch?” “Do you like to kiss her while we're in action?” Ask her the limits, then ask him what he would enjoy seeing and make sure it is okay with her.

The biggest thing you are doing is keeping him involved in the conversation.

It may not seem like much, but it's what gets Mr. Happy happy, her kitty happy and her partner smiling... and maybe asking you back again.

Again, it's not like golf... here you are trying to hit a hole in one every time.

Judy socializing with a Single Gentleman
Real-photo break

Always Keep Both People Involved

The quickest way to lose the invitation is to make one half of the couple feel like an obstacle between you and the person you really want.

Talk to both of them. Compliment both of them. Ask questions of both of them. When play is being discussed, make sure both of them still feel like part of the conversation.

You are approaching a couple... not a lady who happens to have inconvenient furniture standing beside her.

Don't Oversell Yourself

Confidence is attractive. A résumé containing your dimensions, sexual endurance records and testimonials from allegedly satisfied women is considerably less impressive than real conversation.

Leave some things as a surprise unless, of course, they ask.

Being self-assured can be as intoxicating as the wine in her hand. If you get to this point, her partner should be giving you the go-ahead signs.

Don't confuse them with directions to the parking lot.

Judy with a reader holding a Forever Isn't Boring book

Want to See How This Works in Real Life?

Find out how Judy handles Single Gentlemen in nearly every book.

The advice is here. The stories of what actually happened... those somehow ended up in the books.

Forever Isn't Boring... Marriage With a Flexible Guest List book coverMarriage With a Flexible Guest ListWhy is butter the key to the first date?
Forever Isn't Boring... Destinations, Decadence & Bad Decisions book coverDestinations, Decadence & Bad DecisionsIs there a stripper in our bed?
Forever Isn't Boring... Age Has Nothing to Do With It book coverAge Has Nothing to Do With ItWhat is a Grilled Dicky Award?
Forever Isn't Boring... From Cootie Corner to Bora Bora book coverFrom Cootie Corner to Bora BoraWhat is an Energizer Unicorn?

Be Reliable

If you make plans, show up... on time. If something changes, communicate. Somehow, someway. Even Roman candles if you have them.

Better to be early, have a small drink to ease your nerves and maybe make conversation easier.

Start with a compliment for both of them. For her... maybe a lovely outfit. For him... what an amazing lady.

Couples remember the gentleman they can trust, even when they may think the compliment is not quite sincere.

They know you are earning your place.

Never Be Pushy

This is worse than drama.

Yes, you paid a lot of money to get here, but that doesn't mean they owe you sex. Interest isn't something you can negotiate into existence.

If a couple or person is hesitant, back off. If they are interested, it should generally be clear without having to wear them down.

A gentleman gets invited. A salesman keeps pitching after everybody has already said no.

Ready to Try This in the Real World?

Here are a few places Hugh and Judy actually go. Come for the trip, the people and the fun... the rest is not included in your cruise fare.

Now Booking

Hedonism II Jamaica

October 10 to 17, 2026

Seven nights of fun, friends and unforgettable memories.

Limited Cabins

Bliss Cruise

February 24 to 28, 2027

Four nights aboard one of the world's largest lifestyle cruises.

Couples Welcome

Hedonism II Jamaica

May 1 to 8, 2027

Another week in Jamaica with Hugh, Judy and lifestyle friends.

Booking Now

Hawaii and Tahiti Cruise

June 29 to July 11, 2027

12 days, 8 ports and a South Pacific adventure with lifestyle friends.

Let's Start Online

We're talking about sites like SLS, SDC, Kasidie and the other places where couples and singles meet. Before you ever get to the room, you have to survive the inbox.

They Say “No Single Men?” Believe Them.

You can certainly look at their profile, but don't be creepy and don't contact them anyway.

“No single men” does not mean:
“No single men... unless you happen to be really persuasive.”

It means no single men.

If they see something they like about your profile, they can reach out to you. You aren't going to impress everyone, and you don't need to.

Say Something Besides “Hello”

“Hello.” “Hey.” “What's up?”

Those aren't introductions. That's what you say when you accidentally make eye contact with somebody at Walmart.

I saw your photos and you two look like an interesting couple. Take a moment and look over my profile and let me know what you think.

Notice something? We included him.

You're approaching a couple. Be prepared to talk with him as much as... and sometimes more than... you talk with her.

Besides, if he likes you, you've already got somebody on the inside doing your advertising.

Keep Mr. Happy in His Wrapper

Do not send a dick pic unless they ask for one.

Yes, it may be your best feature. That's wonderful. Let's play a little coy at first.

Hopefully you can talk and write well enough to make somebody interested in the person attached to it.

If not... run what you're about to send through AI.

At least pretend you have a brain until the real date.

Go Over the Rules Before the Clothing Starts Coming Off

Everything you can remember. What's a no, what's a yes and what's an “I don't know yet.”

KissingCondomsWhere to leave the DNAAnalIs the partner playing?Male-on-male contact?

There is more, but some things you have to figure out.

This is not one-on-one instruction. You didn't pay enough for those lessons.

Get your hand on the wrong cookie and there may only be a stub left... and this game will be called for interference.

Learn How to Handle Rejection

You are going to hear no. Maybe often. That's part of being a Single Gentleman in the lifestyle.

Do not argue, pout, demand an explanation or send a nasty message. Nobody came here for drama, and drama has a nasty habit of ruining future possibilities.

Smile, step away and be gracious. Something as simple as, “Maybe another time then...” works just fine.

The gentleman who handles “no” well is a lot easier to remember fondly than the “gentleman” who turns it into a congressional hearing.

The Encore Is the Point

The goal isn't getting invited into bed once. It's getting those repeat encore performances... often.

Good performances get good recommendations, and pretty soon your dance card will be full most weekends.

How you explain that to your girlfriend is your problem.

Still Need More Instruction?

Judy has been dealing with Single Gentlemen for years. Somehow Hugh keeps writing about it.

Forever Isn't Boring... Marriage With a Flexible Guest List book coverMarriage With a Flexible Guest ListBook One
Forever Isn't Boring... Destinations, Decadence & Bad Decisions book coverDestinations, Decadence & Bad DecisionsBook Two
Forever Isn't Boring... Age Has Nothing to Do With It book coverAge Has Nothing to Do With ItBook Three
Forever Isn't Boring... From Cootie Corner to Bora Bora book coverFrom Cootie Corner to Bora BoraBook Four