Breakups & Cheating
December 17, 2019

Justin Timberlake’s “Cheating” Story Is A Good Lesson in Boundaries For Us All

Every partnership sets its own boundaries for what constitutes cheating.
Written by
Gabi Conti
Published on
December 17, 2019
Updated on
What's changed?
Discover a world of pleasure with our handpicked, high-quality, and beautiful products, curated with your trust, discretion and body safety in mind. Shop now at

In late November, the Internet was shook after paparazzi released photos and videos of Justin Timberlake and his Palmer costar Alisha Wainwright holding hands (and thighs) on a balcony after filming. The singer has been married to his wife, actor Jessica Biel, since 2012 and they have a 4-year-old son together, so gossip about a potential affair spread quickly.

Timberlake took to Instagram to publicly apologize for the embarrassing situation he’d put his wife and family in, stating that he was drunk, that nothing beyond what had been captured happened between him and Wainwright, and that he’s excited for us all to see his new movie. Us Weekly reports that Jessica Biel asked Timberlake to make a public statement because she felt embarrassed by his behavior, but neither Biel nor Timberlake has personally confirmed this information.

The fact is that the Timberlake scandal is a private matter, and there’s no way we could know what’s really going on behind the closed doors of the Timberlake/Biel household, nor is it any of our business. 

Every couple sets their own boundaries for what behaviors constitute cheating, and people in relationships make mistakes. 

Ultimately, it’s up to each partner to decide which kinds of mistakes are forgivable. This is not an attempt to celebrate or justify Timberlake’s actions, but rather to open up a discussion about cheating in our own relationships. I know some people may disagree with me, but I don’t think cheating is always a black and white issue where the cheater is wrong and the person who was cheated on is right. I know that I feel this way because I have been cheated on and I have been the one to cheat on a partner. After these personal experiences, I realized that infidelity can be a more nuanced issue than it’s portrayed in the media — and while we know nothing about how Biel and Timberlake really feel after this controversy, I think it gives us an opportunity to examine how we discuss cheating in general.

I cheated on my ex-boyfriend when I was kissed by a guy friend and I kissed him back. 

I’d already felt trapped in an unhealthy relationship with my boyfriend at the time and struggled to end things. I should’ve broken up with him before my friend even kissed me, but I didn’t. When I recently shared my experience in an essay for HelloGiggles, I was mostly attacked by strangers who went out of their way to direct message me on social media. These strangers had also been cheated on, so I can understand their anger. But I also received kind words from strangers who thanked me for the piece because they’d been in similar situations where they felt trapped, and they said my essay helped them stop beating themselves up.

No matter where you stand on this cheating spectrum, let’s take a closer look at how this affects couples.  

Cheating isn’t always easy to define, as Raffi Bilek, LCSW-C, couple’s counselor and Director of the Baltimore Therapy Center, tells “For some couples, a little flirting with other people is no big deal; for others, it's over the line. In open relationships, it might be acceptable to have sex with people outside the couple, but even in such cases, cheating is possible. For example, a couple involved in an open relationship may agree that it's okay to sleep with someone else so long as your partner knows — and if you are keeping it secret, that's cheating. So looking from the outside, we can't really say what is or isn't cheating. That's really up to the couple.” So, if cheating is really between partners, should we be so quick to judge a couple based on actions that look like cheating? We don’t know what their agreement is

Rabbi Shlomo Slatkin, a licensed clinical professional counselor and co-founder of The Marriage Restoration Project, tells a precise definition, saying that cheating is “any violation of relationship boundaries that are expected given the nature of the relationship. When one breaks the boundaries, they break the trust in the relationship.”

Dr. Fran Walfish, a family and relationship psychotherapist and author of The Self-Aware Parent, tells how emotional affairs with no physical contact can be a type of cheating. According to Dr. Walfish, emotional affairs can happen, “as a mechanism for avoiding true intimacy with [a] partner/spouse. [A partner may] withhold communication of their feelings and share them with an outsider to keep a wedge between them and their spouse. This maintains a disconnect or distance in the [relationship].” 

If cheating — as a couple defines it — does occur, partners can and do survive it.

Tina B. Tessina, Ph.D. (aka Dr. Romance), psychotherapist and author of Dr. Romance's Guide to Finding Love Today, tells how to work towards forgiveness in these situations, if that’s what partners want to do: “As long as you're stuck in blaming each other and defending yourself, you won't be able to move forward. Forgiving each other doesn't mean condoning what happened, or that it would be OK if it happened again. What it does mean is that you're willing to close that chapter and move on.” 

Here’s hoping that Timberlake and Biel are able to move on and enjoy a happy relationship, but no matter what they choose to do, it’s not our business. Any form of cheating is a private matter for the partners experiencing it, and how they proceed is up to them.

Reviewed for Medical Accuracy

Gabi Conti is a writer, host, comedian, storyteller, and author. Gabi went on ten thousand hours worth of dates in her 20s (so she calls herself a "sex columnist" but her mom still calls her "a disappointment"), and attempted to go on 30 dates in 3 days in her 30s. She's sharing her knowledge in her book 20 Guys You Date in Your 20s, which comes out May 2020 with Chronicle. She's done on camera hosting for BrotherHQ, Hollywire, and The Elite Daily Show, and has contributed to Cosmopolitan, Hello Giggles, Elite Daily, Mind Body Green, Brit+Co, POPSUGAR, and Thought Catalog. She's very active on Instagram, so follow her there: @itsgabiconti.

Oschool logo

Why shop with us

Shop with us for high-quality, body-safe sex toys that are backed by expert-led education on pleasure, consent, and sexual wellness.

What we stand for

Our commitment to inclusivity and social justice means that your purchase supports causes that matter.

We believe in safe spaces

Your privacy is our top priority, so you can shop with confidence and focus on exploring your pleasure without any worries.

Order Form

We want to help you get the orgasm you desire.
Let's get it on keeps this information totally private and anonymous.