Is It Cheating If You’re Not Official?

Your Ethical Dilemma

It begins with a question from a reader that you may be able to relate to.

I’ve been dating this girl for about a month, and things are going great. We have not had any problems, and we both see a long future for us. We met through a dating site and talked a few weeks before our first date.

The problem I am dealing with is that I had a one-night stand after a long night at the bar a couple of days after our first date. I feel bad about it every time I think about it, and I feel even worse every time the girl I’m dating brings up the fact of how she can trust me and how she loves how honest I am with her.

So my question to you is when would be the appropriate time for me to tell her about this, and if there is no right time, then what should I do so this doesn’t eat me up alive every time I think about it?

(I feel this is one of those things where telling her would be an easy way for me to feel better but would end up doing more harm than good in the end.) —Jason

Jason,

Your radar is right on the money.

You’re considered honest and trustworthy by your girlfriend.

You care about her and see a potential future with her.

You feel bad that you were with someone in the time that you knew her.

You want to get this guilt off your chest and aren’t quite sure how she’d take it.

Yep. Your heart’s in the right place.

Is your past infidelity relevant to your current relationship?

The only difference between you and me is that I don’t think you’ve done anything wrong. 

This is very similar to a post I wrote a few years back, where a guy’s girlfriend dumped him, he had a one-night stand, and then they got back together.

I didn’t think he did anything wrong either. But that doesn’t mean that his girlfriend would agree.

And that’s why this situation is more grey than black and white.

Reasons why you shouldn’t worry 

Still, I’ve got three compelling reasons why you should give yourself a break and just focus on being the best boyfriend you can be, okay?

1. You can only cheat if you have a commitment.

You can only cheat if you have a commitment.

And a couple of days after your first date, how did you know that your current girlfriend might be “the one?” That’s right; you couldn’t.

First dates are about having fun, connecting, and seeing if there’s enough potential for a second date. It would be downright foolhardy to commit to someone after a first date (even though we’ve all done it).

So really, Jason, if you didn’t have a girlfriend when you had your one-night stand, you didn’t actually cheat. You were just a slut. That’s different.

2. There is little upside to telling your girlfriend the truth.

The downside, however, is tremendous. 

I speak from experience. I remember, once upon a time, I had a jealous girlfriend who’d been cheated on by previous boyfriends. 

And our conversation went something like this:

Her: “If you ever cheated on me, I’d expect you to tell me about it.”

Me: “What would happen if I told you about it? Would you have the capacity to forgive me for a one-time indiscretion?

Her: “No, I’d dump you and never forgive you.”

Me: “Then what incentive would I have to tell you the truth if it meant you’d dump me?”

Her, after a pause: “Well, that’s what a real man would do!”

And scene.

This ridiculous conversation took place probably 5 times in our six-month relationship, where she told me that I’d better tell her the truth if I cheated and I parroted back the only answer I could, “If I ever cheated, you can be sure I wouldn’t tell you about it.”

A rule of thumb: If you know that your girlfriend can’t handle the truth, don’t tell her the truth

I share this aside from your original question because I think it’s interesting and relevant.

If you tell a man that you will never accept his truth: 

-He’s sometimes attracted to other women

-He’s occasionally going to have lunch with an ex-girlfriend

-He may keep photos from his past in an album stored in his closet

-He worries at times he feels trapped in the relationship… 

Guess what? You are all but begging that man to LIE to you.

If you accept his unsightly truths, you can have a man who is comfortable being himself around you…and a man who is himself around you is a man who will marry you.

A man who is forced to tell lies by a girlfriend who doesn’t accept him will eventually leave to find a less oppressive environment.

A man who is forced to tell lies by a girlfriend who doesn’t accept him will eventually leave to find a less oppressive environment.

And so, my friend, Jason, if you don’t know that your girlfriend can handle the truth, don’t tell her the truth. In the same way, you don’t tell her how many people you’ve slept with in your life; some things are on a need to know basis, and if you’re a devoted boyfriend now and have no intentions of ever leaving her, that’s all she needs to know.

3. The other reason that I know that you’re not a bad guy is this.

I had the same thing happen to me in 2007.

I first dated a cool woman in LA, followed by a weekend hookup in San Francisco with someone I’d met. But after I came home, I focused my energies on the really cool woman in LA.

Three weeks later, we were exclusive. 

A year and a half later, we were engaged.

15 years later, we’re still married. 

I don’t know at what point my wife found out about the San Francisco woman, but, at that point, it was water under the bridge. We were already in love, and what I did in the first week of knowing her was pretty irrelevant to the relationship we’d already built.

The fact that my wife kept her Match.com account alive for the first two months of our relationship didn’t impact my trust in her either.

You sound like a sweet guy. Go make this girl happy and give yourself a break.

And if she’s cool, she should be able to handle the truth…eventually.