I Was Unfaithful to My Girlfriend Before She Was My Girlfriend. Should I Tell Her?

I Was Unfaithful to My Girlfriend Before She Was My Girlfriend. Should I Tell Her?

So 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 the both of us together. We actually met through a dating site and we were talking a few weeks before our first date. The problem I am dealing with is that a couple days after our first date, I actually had a one-night stand after a long night at the bar. I feel bad about it every time I think about 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 not an appropriate time, than what should do I do so this doesn’t eat me up alive every time I think about? (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


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.

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.

You can only cheat if you have a commitment.

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 a little murkier than black and white.

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. And a couple of days after your first date, how were you to 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. If you read this blog, you’ll know that I’m as honest as they come. This, of course, is not necessarily a good thing, but people around me have always known where I stood. 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 man who is forced to tell lies by a girlfriend who doesn’t accept him will eventually leave to find a less oppressive environment.

I share this as an aside to your original question, because I think it’s interesting and relevant. If you tell a man that you will never accept his truth: that he’s attracted to other women, that he’s going to have lunch with an ex-girlfriend, that he keeps photos from his past in an album stored in his closet, that sometimes 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.

And so, my friend, Jason, if you don’t know that your girlfriend can handle the truth, don’t tell her the truth. 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 exact thing happen to me in 2007. First date with a really cool woman in LA, followed by a weekend hookup in San Francisco with someone I’d met prior. 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.

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.

Oh, and the fact that my wife kept her Match.com account alive for the first two months of our relationship didn’t impact my trust towards 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.

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  1. 1

    I don’t think you have done anything wrong.
    Many people don’t even think of a first date as a “date” if it is the result of an online conversation.   It is a “meet and greet”,   you have not met the person.     How can you cheat on someone you have only met once?
    I’m assuming your first “date” didn’t include “the talk” to date exclusively and I’m assuming you didn’t get more physical than a hug or a kiss.
    You didn’t enter into any agreement, explicit or implicit, so there is no agreement to have cheated on.
    Your problem is not a wrong doing on your part, but mistaken feelings of guilt that you need to think through and drop.
    Keep your mouth shut about your one night stand.
    When you have dated this woman long enough to make it fair for her to ask about your past relationship, tell her about your past relationships.     Unless she tells you about every single one night stand she had, don’t tell her about your one night stand.

  2. 2
    Nadia Shore

    I don’t think the average woman assumes that a man is exclusive just because of one date. Whenever I am getting to know someone new, my assumption is that we are both keeping ourselves open to other people until there is a reason not to. How do you know that she didn’t get her ya ya’s out with someone else herself? Jason sounds like a nice guy for him to be worried about this, but I agree, he hasn’t done anything wrong and there’s no need to confess. Ever.  

  3. 3

    “Unless she tells you about every single one night stand she had, don’t tell her about your one night stand.”   I would argue that even if she were to tell him all about her one-night stands, that he doesn’t have to tell her about his.   I mean, in an earlier blog post, you wrote about the value of discretion regarding previous encounters…
    In any case, I agree that this guy has no obligation to tell his now-girlfriend about what he did before they became exclusive (if anything, his obligation is to NOT introduce this possibly confusing/ toxic piece of information into their relationship).   As long as he remains faithful now that they’re in a relationship, he’s in the clear.  

  4. 4
    Still Looking

    Jason –
    With internet dating I assume every woman I contact is in contact with multiple men.   When I start talking with her on the phone I assume she is still talking with other men.   If we meet, I assume that she is still meeting other men and could very likely have dates set up for later in the week with other men.   Quite simply I’d be a bit worried about her emotional impulsiveness if she was focusing exclusively on me so quickly.

    There’s an unspoken rule that until there is an agreement to be exclusive, the relationship is not exclusive.   This agreement can be either explicit or based on actions (dating every day, moving in together, etc.) but to avoid any confusion the explicit agreement works best.

    Sometimes the mere passage of time can lead two parties to believe the relationship is exclusive.   That could be 6 weeks, 6 months, or some other time period but certainly not one date unless you led her to believe during your first date that she was the one for you and you were taking yourself off the dating market immediately.

  5. 5

    Agreed. I think you’re over thinking here, Jason. 🙂

  6. 6

    The fact that you are agonizing about this shows what a good hearted guy you are. Do NOT tell her a thing, until she is your long-term girlfriend! Even then it isnt necessary. You have misplaced guilt going on here. Telling her now would be an act of major self sabotage. This is your issue to work out on your own. I hope you enjoy the new beginning you’ve created with her, and refuse to let this silly nothing ruin it!

  7. 7

    Evan, this is great advice!
    Jason, I really don’t think you did anything wrong, and I certainly believe you should refrain from telling your girlfriend. This situation must come up the whole time in this era of dating multiple people until you click with one particular person, and you can’t be blamed for not being psychic after a first date.
    If you really feel you must tell your girlfriend, I strongly counsel you to wait. You and she obviously have a strong initial connection, but the fact of the matter is that you have only been together for a month, and don’t know each other very well. If you tell her now, she only has four or five weeks of “good” behaviour to compare your one night stand to. If you give her more time to find out that you are a decent, honourable man and a devoted boyfriend, she will be able to judge whether your one night stand represents the real you, and reach the correct conclusion that it is irrelevant to the relationship.

  8. 8

    Give yourself a break and let it go. Guilt is a healthy emotion that is suppose to be there when we’ve done something wrong. But you haven’t done anything wrong. I understand that you regret the one night stand and wish you had never done it, but just because you’re burdened with it don’t also burden your girlfriend.
    What is she to do with this information? Why do you want the thought of you with another woman swimming around in her head?? Give your misplaced guilt to God and move on. You did not cheat on her. And frankly, you don’t owe each other every sorted detail of your past sexual lives. Sharing with each other about relationships you’ve each had is one thing, but you can still be an “honest, truthful” guy without sharing this event or any other meaningless sexual event with her.
    If I was her, I wouldn’t want to know. There’s no value-add to telling her about this. Move on, and forget about it.

  9. 10

    Good call again by EMK.   If you guys get serious (i.e. engaged), you should probably tell her about it so that — just in case — it doesn’t come back to haunt you in the long run.   If you’re an open book like me, you might say something anyway (or see your hookup somewhere), so best to put your cards on the table before getting married, but definitely not now.
    You sound like a great guy.   Best of luck to you!!!

  10. 11

    I agree with everyone else that Jason didn’t do anything wrong. I don’t know what he and his girlfriend agreed to after that first date, but i doubt that they agreed to be exclusive that quickly, even if they both enthusiastically agreed to move forward. Still, I wish every man were as thoughtful and caring as Jason is!

  11. 12

    If I were in your girlfriend’s shoes, I’d be happier not knowing. There’s no good reason to tell her about a one-time event. It couldn’t possibly benefit her or your relationship.
    If and when the conversation about “our past relationships” comes up, there’s also no need to tell each other every intimate detail and blow-by-blow. Just the basics of who, how long, and why it didn’t work out are all she needs to know. Your one-night stand doesn’t even qualify as a “relationship” in my book. Leave it out.
    I respectfully disagree with Evan that the one-night stand made you a “slut,” if only for one night. If you had a long-standing pattern of such pick-ups, that might qualify as slutty. The remorse you expressed in your letter suggests you aren’t like that.
    I enjoyed your letter, Jason. It’s cool to hear a man express such strength of conscience.

  12. 13

    Jason, I don’t think you did anything wrong. There is a chance your girlfriend won’t think you did anything wrong too! I like the idea of telling her after you’ve been dating a bit  longer, but would understand if you chose not to as well.

  13. 14

    Jason doesn’t say this in his post, but one reason that he might feel a bit guilty is if the topic of dating other people came up on their first date, and he said he wasn’t dating other women.   While I’m sure most seasoned readers of this blog follow the don’t ask don’t tell rule, not everyone does.   I think even if this scenario is true, he still wasn’t cheating on her because she was not his girlfriend.   However, he might feel guilty because by saying   he wasn’t dating other women, he was suggesting that no other women were in the picture and so it would be less likely that he would sleep with someone– but a few days later he did.    He might feel guilty because he followed the letter of the law, but not the spirit of the law.   Otherwise, his guilt and being torn apart just doesn’t make any sense to me.   You are not cheating on someone if that someone is not your girlfriend.

  14. 15

    I agree with Laurie that Evan’s remark calling him a “slut” for his 1 one night stand is a little presumptuous but in all reality I’m sure it wasn’t his first or only one and it’s not her business anyway.

    Never the less, of course Jason did nothing wrong. He just feels guilty due to the fact that when you’re really into someone new they may judge you on certain things you do or have done in your past and it  may  lower your value in their eyes. Some people(probably more so  women) pass judgement on ANYONE who’s ever had a one night stand.

  15. 16

    Jason you need to forgive yourself.   Even if you feel it was an indiscretion, let it go.   If you both understood there was no exclusivity at the point in which the one night stand happened, it’s really not germain to the situation.

  16. 17

    You did nothing wrong. BUT if its eating you up, you have to tell her. Because its about being honest, even EMK said so. Hes practically bragged about being honest in all his articles except this one of course.

    He even told his wife  he thought he was going to be with a jewish atheist from the east coast, etc and backed  it up with “its about honesty” and  so go ahead and tell your  girlfriend about it. EMK’s wife didnt leave him, how do you know yours will? She will probably be just a tad upset Im sure, but your honesty will make the relationship  stronger.     

  17. 18

    Let it go.

    This is the only other thing that I can add to Evan and the other posters’ comments.

    Jason, I think you are putting too much pressure on yourself on many levels.   If you went on a first date / meet and greet with a woman from the internet, you by no means have any obligation to her.   But ALSO, it is really rushed to say a good first month means you can see a long future together.   I think you are rushing things on many levels, although I do think it is wonderful you and your girlfriend are clicking so well and things are going so great.

    I think this is more about regret, because you’ve essentially tarnished this nearly-perfect start to a relationship, but the best thing to do is drop it.   Dumping this on her is just creating unnecessary drama when you should just be enjoying how smoothly things are going.   Relationships have enough challenges w/o adding on unnecessary ones.

    If you and your girlfriend don’t work out, keep in mind your current feelings this time for future relationships and be conscious of your behavior’s affects on your emotions.   This isn’t an “us” issue in your relationship.   It’s a you issue.

  18. 19
    50 Proposals

    I agree with everyone else…until you have the exclusive relationship talk there’s no obligation.   She would definitely be happier not knowing.

  19. 20

    Jason: Take it from a woman.   She doesn’t want to know. It’s not relevant to the present or the possible future. There is simply no upside. It’s like dropping a turd in someone’s pocket. Once it’s there, they’ve got to do something about it although they’d really rather not. Quell your guilt by being an honest boyfriend  now  and  in the future. Few, if any, of us have impeccable dating histories.   

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