Relationships

How to Talk to Your Girlfriend About Trying Anal Sex

December 9

How the Figging Kink Can Fire Up Your Sex Life

December 7

Confessions of a Love Bomber

December 7

The Secret to Meeting the Right People

December 6

What Is Polyamory? A Guide to Open Relationships

December 2

This Holiday Season, Give the Gift of Anal

December 2

No, Your Ex Doesn’t Need Your ‘Gift’ of Friendship This Holiday

November 30

5 Tenga Sex Toys You Can’t Live Without

November 26

On Dating Younger: When Does Her Age Become a Problem?

November 24

Dating a Hacker Is a Dark Web

November 23

The Rise of Dating ‘Situationships’

November 21

The Mirror Kink and How It Can Promote Confidence

November 19

Anytime? Anywhere? The ‘Free Use’ Sex Kink

November 18

Are Some People Just Slapping the ‘Poly’ Label on Their Cheating?

November 17

The Secret Sex Lives of Porn Stars

November 16

Once Upon a Cosplay

November 16

Should You Join Your Best Friend’s Threesome?

November 16

Why Vasectomies are Cool, Actually

November 15

Can You ‘Open’ a Relationship While You’re Already In One?

November 13

Art of Exposure: A Guide to Sexual Exhibitionism and Voyeurism

November 12

Getting Those Digits: A Gentleman’s Guide to Fingering

November 10

How to Handle It If You’re Afraid of Sex

November 6

How Do You Deal With Virtual Cheating?

November 2

To Ghost Or Not To Ghost?

October 31

Playboy’s BDSM for Beginners Guide

October 31

You Like Vanilla Sex. What If Your Partner Craves Kink?

October 29

A Guide to Cybersex From a Cam Girl

October 27

Can Bad Sex Ruin a Relationship?

October 26

The Forbidden Fruit: Tips for Anilingus — a.k.a. ‘Eating Ass’

October 26

What to Do If You Had Sex With Your Friend

October 24

How to Stop Premature Ejaculation in a Few Easy Steps

October 21

Long-Distance Relationships Are Not Doomed to Fail

October 21

First Date Jitters? Try Playboy’s 5 Top Tips for the Big Night

October 19

The ‘Noah’ Effect – Are Nice Guys Finally Trending?

October 19

In Defense of Foreplay, the Overlooked Key to Great Sex

October 18

Can You Have a Relationship With a Sex Mismatch?

October 17

Dear Playboy Advisor: Depression Is Ruining My Sex Life

October 17

5 Life Tips That Apply to Sex (or Sex Tips That Apply to Life)

October 16

How to Have the Group Sex Conversation (and Not Get Slapped)

October 15

Going Down? Good Oral Sex Starts With Talking

October 14

Morning Sex – Yay or Nay?

October 13

Meet the Women Who Design Sex Toys for Men

October 13

Your Dog May Save Your Sex Life

October 12

How (Not) to Get Your Ex Back

October 12

How to Talk Dirty, Not Cringy

October 12

Sex Shame Is Real. How to Fight It

October 10

When Is a Safeword Not Really a Safeword?

October 9

The Best Sex Trick You’re Not Using

October 9

Are We All Liars in the Beginning of Relationships?

October 6

The Crazy-Hot Matrix, Explained

October 5

Did the Rich and Famous Ruin OnlyFans for Sex Workers?

October 4

The Future of Sex Toys Is Gender Neutral

October 3

What the World Ignores About Vaginas

September 24

Men Need Sex Toys, Too

September 15

Escorts Need Love Too: The Story Behind Our Story

September 14

Gal Ritchie’s 5 No-No’s in the Bedroom

September 13

Riley Reid’s Very Best Dating and Sex Advice for Guys

September 13

Confessions of a Burnt Out Submissive Brat With a Praise Kink

September 10

Joel Kim Booster on Sex Education

September 7

Sex Workers Are Coding Their Own Futures

September 1

What Makes a Perfect Penis, According to Science

August 31

BDSM Isn’t Just Good for Your Libido, But Your Mental Health Too

August 11

Dear Playboy Advisor: Can Weed Help Me Revive My Sex Life?

August 8

Dear Playboy Advisor: How Do I Unlock the Pleasure of the Prostate?

October 15