Single Gentlemen • Swinger Lifestyle Advice

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 together
The recurring rule on this page: keep both people involved.

First... Be Someone People Actually Want Around

Before technique, equipment or bedroom heroics... start by being social, clean and enjoyable company. Radical concept, we know.

We’ll give you the part that matters first. Want the rest? Open “More Insight.”

Be Social Without Expecting Sex

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

Believe it or not, couples can smell the “I came here expecting sex” attitude... and you might reek.

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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.

Clean Up Before You Show Up

Take a bath just before going. Do not bathe in cologne. Brush your teeth.

Do not rinse with Fireball and think that is enough.

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Wear nice clothes. No, we are not talking about $100 shirts... just 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.

How to Approach a Couple Without Becoming the Story They Tell Tomorrow

The short answer is simple: you're approaching a couple. The longer answer is where a lot of Single Gentlemen get themselves into trouble.

Judy socializing with a Single Gentleman

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.

Make Friends With the Male Partner

This one is very important. You are not there to pretend her partner is invisible.

Keep him involved and you may discover you already have somebody on the inside doing your advertising.

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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.

Don't Oversell Yourself

Confidence is attractive. A sexual résumé with dimensions and endurance records is considerably less impressive than real conversation.

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

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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?

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

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

FOREVER Isn't Boring Book 1 cover

Marriage With a Flexible Guest List

Why is butter the key to the first date?

Book 1 on Amazon
FOREVER Isn't Boring Book 2 cover

Destinations, Decadence & Bad Decisions

Is there a stripper in our bed?

Book 2 on Amazon
FOREVER Isn't Boring Book 5 cover

Still Us... Slightly Upgraded

Two men in Judy's bed... a unicorn for a week... apparently we weren't finished.

Book 5 on Amazon

See the Whole FOREVER Isn't Boring Series

The Things That Get You Invited Back

Getting invited once is nice. Becoming the Single Gentleman a couple actually trusts enough to invite again is better.

Be Reliable

If you make plans, show up... on time. If something changes, communicate.

Couples remember the gentleman they can trust.

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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

Yes, you paid a lot of money to get here, but that does not mean anybody owes you sex.

Interest is not something you can negotiate into existence.

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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.

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.

If a profile says “No single men,” believe it. You are not the exception they forgot to mention.

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

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It means no single men.

You can certainly look at their profile, but do not be creepy and do not contact them anyway.

If they see something they like about your profile, they can reach out to you. You are not going to impress everyone, and you do not need to.

Say Something Besides “Hello”

“Hello.” “Hey.” “What's up?” Those are not introductions.

That is what you say when you accidentally make eye contact with somebody at Walmart.

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Try something that shows you actually looked at the profile: “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 are 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 have 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 is wonderful. Let us play a little coy at first.

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

If not... run what you are 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?

More About Rules and Boundaries

The rules conversation happens before the clothing starts coming off... not halfway through when somebody suddenly discovers an objection.

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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 is part of being a Single Gentleman in the lifestyle.

How you handle the no may matter more than you think.

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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.

More Lifestyle Help

If you made it this far, you may be serious. Or you have a very long lunch break.

Swinger Dictionary

Terms, abbreviations and things nobody explained before you joined the lifestyle.

Read the Dictionary →

New Swingers FAQ

Questions people really ask when they are trying to figure out how all this works.

Read the FAQs →

Swinger Club Reviews

We go to the places, look around and tell you what we actually think.

See Club Reviews →

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12 days, 8 ports. Bucket list, Certainly. F_ck it list, Probably. Any more questions.

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