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.

Join our conversation (62 Comments).
Click Here To Leave Your Comment Below.


  1. 31

    This is why I don’t do online dating… I agree with #21.  Stupid stuff like this is par for the course with online daters.

      In real life, when I go on a date with someone, I expect that he is not dating other women or sleeping with other women. 

    I also tend to believe that Jane’s take in #22 is probably on the money.  She probably asked if he was seeing someone, and he pulled a Bill Clinton on her.  He wasn’t actually ‘seeing’ other women, as in spending time with them or dating them…. just having sex.  

    Of course, we don’t know for sure.  Just speculation… but definately would fit the description of  most messed up online dating situations.

    I think he should tell her.  Did he do anything ‘wrong’?  We don’t know the whole situation…

    For people who don’t date or sleep with multiple people simultaneously…  what he did would be a dealbreaker…  I think she deserves to know what his values are upfront, and vice versa.   

  2. 32

    I agree. This is coming from a female perspective, you can not violate a commitment that was never made.

  3. 33

    Hi Kenley
    Yes, you have pointed out something which I didn’t specifically address, which is that someone may still want to cheat and not end their current relationship. I not sure how Evan’s ex could have phrased it simply in one or two sentences. In effect she is saying :
    – if you feel strongly attracted to someone and the opportunity is there to pursue something with this other person, please consider carefully who exactly you want to be with because I don’t want to be cheated on
    – if you feel tempted to cheat in any way, work out why and if there is something wrong with our relationship. Talk to me about any problems first
    –  if you feel tempted to cheat because there is something seriously wrong with our relationship that is beyond repair, please break up with me first.
    -if you want to cheat but still want to be with me because there is nothing wrong with our relationship, then you are not an honorable man and be aware that I will dump your sorry ass the second I find out
    If anyone can summarize this succinctly they deserve the Nobel prize for literature.
    As for Evan’s response. It is not puzzling at all. I suspect that before he became “enlightened”, Evan simply responded in a very logical male way to a statement which did not make logical to his male brain. He simply did not read the subtext underlying what his ex girlfriend was telling him.

  4. 34

    Jason – read my lips – don´t tell her. This does not make you a bad guy. There is so much mistrust in the world between people and relationships  – let her be the exeption of it and build the trust in you. Theres no constructive need to break this, especially if you have such a good thing going on right now.

    I belive,  in your heart you have already *learned your lesson,* which is: feeling bad, confused and writing to our guru-Evan.

    Its early state in your relationship, yes?
    Its time to get to know her more and  grow as couple.


  5. 35
    Laura S.

    I find it amazing so many here approach this issue legalistically, making their call on a technicality rather on the HEART issue it is.    That kind of thinking is a sucky way to try to have a relationship.

  6. 36

    Okay I’ll rephrase what I said earlier, so it doesn’t sound like a legalistic way to get Jason off on a technicality. If he tells his GF, then he gets to have a clear conscience at her expense. He will have offloaded his problems (real or imaginary) on her. Not the best way to try and have a relationship, in my opinion.
    This was the one thing I could not stand back in my religious years, by the way — you were always encouraged to confess your sins to the person you have wronged, even if the only place you have wronged them was in your head. Say I secretly hate my neighbor Jill. From my experience, a staggering number of people would advise me to confess my sin to Jill and ask her forgiveness, and I would instantly feel better. Heck yeah, I would, after getting this off my chest! Jill, on the other hand, would be shocked and hurt to find out I’d been hating her all along, but that’s no longer my problem, right? I have confessed. I’m in the clear. Sheesh.

  7. 37
    Laura S.

    No, Goldie, you’re still looking at it legalistically by seeing it as Jason clearing his conscience by dumping it on the gf making it HER problem.  She may not see it as a problem at all.  We aren’t looking for the weasel hole, those are for weasels.  I think many of us have had enough dealings with weasels in our lives, and perhaps some of us have been the weasel a time or two.

    It is a relationship issue affecting two people.  Jason and his conscience and how it now affects his responses to his girlfriend.   It is an opportunity to learn MORE about each other and build trust.  It’s the chance of a make or break moment.

    I went through this awhile back with my bf over lie he told months and months before.   All the issues surrounding it were cleared up, I thought it was too, but something still wasn’t right.  He would get scared and pull back.   Because I trust and respect him so much, he believed he had to protect me from the lie.  I let him off the hook for it.  He was hiding me from his friends and we were not yet a couple at the time.  

    Now he trusts and respects me completely.  He shares the deep stuff and we are closer than I ever imagined we could be.   I am expecting him to ask THE question in late spring when his house is finished.

  8. 38

    I agree with most everyone else, Jason.  Your girlfriend does not need to know about a one-night stand that happened before the two of you were serious.  Not telling her about it does not make you dishonest or untrustworthy- it simply makes you tactful and considerate of her feelings. Sometimes “over-sharing” can be an emotionally selfish act.  Use the time you would have spent telling your girlfriend about the one-night-stand to instead tell her how stoked you are to be with her and why.  It will be much better for your relationship, and it will be a conversation she’ll be glad to remember.

  9. 39

    Hmm.  We don’t know all the details, so it makes it hard to be certain what should be done.
    Jason, on the face of things, you need to find a way to realize that it’s okay to have other “relationships” prior to committing to one relationship.  It is not okay to have a one night stand after you’re committed, but I assume there was none at the time you had the one night stand.  Barring other possibilities, that event does not make you any less honest or trustworthy.  Withholding that information also does not make you any less honest or trustworthy.  It just makes you kinder.  Because I can assure you that a confession to her at this early date would be at the least painful and uncomfortable for her when there is no need to be.  Forgive yourself – you didn’t do anything wrong and you would be causing harm to confess to her now.  Maybe later, but right now it would only be destructive to her and your relationship.
    The only caveat to the above is if 1) the one night stand was with someone that would be hurtful to her or very likely to be found out by her (friend, coworker, relative, etc) or 2) the one night stand could be potentially harmful to her (unprotected sex).  Especially in the second case, you should see a doctor to be tested and be honest with her if anything is found.  However, if these neither of these conditions is present, save her the pain and yourself the guilt and realize that you are still a great, honest, trustworthy person and give your relationship a chance to grow.

  10. 40

    Jason! Tell her. I have had a very similar situation. I didn’t tell. She build up a bigger and bigger fairytale of our early messages and dates. I almost forgot. But she had a tiny suspicion. And it grew. And a tiny bit of evidence came up. She dug. She started not sleeping. Things came out and got HORRIBLE. I lied (I never lie, she knows that) to “limit the damage”. I couldn’t sleep. The stress was awful.
    My initial indiscretion was perfectly forgiveable but the lack of trust from being deceitful was very nearly not, and I am still having to put in major work to rebuild the trust.
    If it is eating you up most likely it will come out. So come out with it first. You will feel heaps better and your relationship will be better for it.

  11. 41

    No really, I would not tell your girlfriend at all, unless she happens to know the other girlfriend or lives in the same city or knows the same friends.
    Wait a while because, from what you say, you just had a one night stand.
    If you tell her, she might misinterpret this – otherwise, why would you tell her? She could be thinking, hm, why is he telling me this if it was just a one night stand???? And why is he worrying so much about it?
    Seriously – relax.

  12. 42

    That is not cheating but I would tell her to be honest.  Only when you commit through marriage is it cheating.   It is unfortunate you somewhat deceived but honesty is the best way to clear the air and start new.  She made by upset but at least she will know you are an honest person.

  13. 43

    My husband was seeing other women and found out after we were married.  It hurt a lot to find out and feel deceived completely.   I cant trust him now and always feel he is hiding things about his past.  Had he been honest from the start it would have taken away the feeling of distrust.   Now I don’t know if I can stay with him for long term.  I most of the time think of looking for an out just because of the distrust is tearing me up.  He blew it.  now he may loose me forever.   I can’t stand being lied to by anyone and it is the one thing that is a deal breaker.  He says he loves me and he is very open now but too late in my opinion.   You don’t l ie to someone you love EVER….

  14. 44

    I disagree with most of the answers.  If you feel guilty there is a reason and no one’s justification will change that.  It’s about your feelings and if you know something was wrong then it is wrong.  If you take advice from all these answers will it make you feel better?  When 2 people meet and start dating, it is about getting to know each other, having fun and experiencing all those first special moments together that build memories and a foundation of trust and honesty.  If you take advice of those who say you did nothing wrong, then you disregard those special moments that you both have to remember forever.  Those moments are the building blocks that put both if you in a relationship.  How would you feel if she was having sex with other men while you were thinking about her, waiting for her, looking forward to seeing her and learning about her?  You made a mistake and you deserve to be forgiven because you know it was wrong and you are man enough to admit it.  The guilt will not change if you don’t tell her and feelings cannot be ignored or covered up, especially long term feeling of something you did long ago.  Many people tend to justify your actions based on technical data rather than feelings.  If you were just dating and it hurts, it cannot be ignored.  Those first moments of “just dating” is when you learn about a person and what kind of person they are.  Anyone can say it’s ok to have sex with others while dating someone, but what does that say about a person?  Is that what kind of girl you want?  Would you like it if she was having sex with others while you were dating and waiting to have sex with her?  Yes it is normal for people to have sex with others while dating someone new but it demonstrates poor character and poor choices because that is not the way to build a foundation of a future relationship. While that other person is being honorable, you were not.  What was wrong 2000 years ago is still wrong today.  Don’t let others compromise your honesty and integrity and tell her because secrets will prevent you from deeply loving her like she deserves.  I asked many people how they would feel if there partner was having sex with others when they first met even though they were just dating.  They all responded that even though it was not yet exclusive that they would feel very bad and sad. It’s about feelings and feelings are what are important.  Those first dating moments are all about learning who a person is and sex with others while first dating tell you who a person is.  That would not be a good first impression and to keep secrets and say it is ok is just a poor exuse to be selfish.  Tell her you made a terrible choice and a bad mistake but that you have learned and suffered over time because you feel that it was not right.  You are different person now and you have grown and learned through your guilt.  Let her know your mentality is far from those cheating moments and you will be releived but also you must give her all your love and attention to help her get through this.  She will be more angry because you didn’t tell her. 

  15. 45

    I can tell you from personal experience that you should absolutely tell her.  My wife slept with a “friends with benefits” 2 weeks after our first date and then lied about it weeks later when I asked her about it.  That lie stayed buried for almost 10 years of marriage and 3 kids.  When she came clean I was devastated and still struggle with this today.  Honesty is the cornerstone of any good relationship and you have to choose which kind of relationship you want to have.

  16. 46

    I would want to know if my man had a one night stand, cuz I don’t date guys who have one night stands. Keep it in your pants..Yuck….Ewwww….Vomit!!!!

  17. 47

    I think most people are wrong to say he did nothing wrong. Dating should be about feelings and bonding and not about the technicalities of how long they had been dating or if there had been the talk about commitment. I just don’t get the “date and sleep with multiple people thing because everyone else is doing it so she should assume that you are doing it as well” what happened to talking about things openly? I’m glad this guy is at least decent enough to feel guilty about what he did. You people sound like dating machines with absolute disregard for emotions and feelings.

  18. 48

    And what kind of relationships are you looking to build? It’s not imposing moral values but just taking into consideration another person’s feelings is or should be a big deal in a relationship. I know that some people need 20 dates to bond but others only need one date and it shouldn’t matter whether or not you had talked about commitment. Because technicalities shouldn’t have a place in relationships. What’s next? A scorecard? Looks like most people here just want to get married and will do just about anything for a husband or wife, including lying  manipulation and changing their core beliefs to get there!!

    I bet most of you would be hurt to find out that your S.O. Slept with someone right after your first date. It’s okay to have feelings you know??

  19. 49

    God. I so wish there were more mature, stand up guys like you two.

  20. 50
    Tiger Lily

    If you have ever been tangled up with a cheater (fill in the blanks to describe the scenario), and you’re still not beyond those icky, sticky, gross feelings not to mention the total shock when you learned you were being cheated on or innocently part of a “cheating pool,” it’s really hard to not think, “Oh, we go again, history is about to repeat itself, I’m outta here.” If Jason brought his news to me, I’d be more concerned about why he’s sitting in bar getting slammed. The problem starts at the beginning.

  21. 51

    This post actually really helped me. For a second I thought this post was actually written by my boyfriend until I saw the name. My boyfriend did have sex with someone before we were exclusive. He told me and I was cool until I had time to sit with it and then my mind started spinning and I couldn’t sleep. I got wrapped up in my head thinking what it meant and if he was ready for a long term relationship or still looking for something casual. Now I realize it was just the beginning stages and I was unsure where it was going myself. I am glad he told me because we were both tested for stds prior to having sex and the one night stand does change the time table. I think you should decide what kind of relationship you want. If you want an open and honest relationship you should tell her. If she is the right person for the relationship you want then eventually she will come around, but be prepared for her to need to take a minute. Yes, we were online dating and I understood we were not exclusive, but I was not thrilled about.  I do realize not everyone can be logical with this (man or women) , but what do you want in your partnership. If she needs some extra help send her a link to this post. It helped me see it from an outside perspective.

  22. 52

    Are we gonna ignore the fact that Evan said if he cheated on a girl he wouldn’t tell her? Bro you are in no place to be giving advice. Personally I would want to know if someone had fucked someone else after a date with me as if I knew at the time I would not have pursued a relationship with them. She deserves to make decisions with all the facts. She deserves to protect herself against STDs too…

    1. 52.1
      Evan Marc Katz

      Everyone is ignoring that “fact” because I didn’t say that. I told the story of one particular jealous girlfriend who made it very clear that if I cheated, she would dump me, thereby ensuring that I had no incentive to tell the truth. As it stands, if I ever cheated on my wife, I would tell her because I think she’d have the capacity to potentially forgive.

      These are all just hypotheticals, of course, because I have a fierce ethical streak and would sooner break up with someone than cheat…and if I did cheat, I’d probably be anxious and vomiting because of how guilty I feel.

  23. 53

    From a moral view he did nothing wrong, there was no commitment.  He also was not seeing anyone else he answered correctly nor did he intend on it as far as we know.  The one night stand happened after they had that conversation on the first date not before.   With online dating you have zero connection on a first date. It’s not like you are going out with someone you know and have now asked out.  For all you know you could show up and meet a total different person that the picture.  So you assume they are seeing others lots of others until commitment.  Why she asked if he was and why he feels so guilty is perplexing but part of me wonders if she expressed that she had been burned by online dating before and so he feels particularly guilty.  I have dated many online men for months who told me they were exclusive called me their girlfriend etc only to find out that they were telling three other women that.  It happens a lot.  I would never expect a man to commit on the first date but I may have said please just be honest later on.  She may have told him this so he feels more guilty or he’s the guilty type but there is some reason for this overly burning guilt so early on.  If it’s that he’s just really that type of guy that feels the guilt he’s going to have to tell her why? Because he won’t be able to get past it it will eat him alive and he will blurt it out eventually.  I know this is not what he should do but with people who can’t deal with guilt (usually raised Catholic :)) this will come out.  He comes clean she accepts it and who he is or leaves.

    If however his guilt is because she told him something about herself that is causing it then he needs to tell her now.  I think this is more likely.  In this scenario he is also a good guy.  A good normal guy who is ready to committ on a normal timeline and was behaving as a normal guy would in having a one night stand.  But feels bad for hurting a girl whom he cares about who shared her past or insecurities with him and he blew it.  He knows if she finds this out she will be really hurt and he’s right.  But it’s because she has her own healing to do not because he did something wrong.  See people don’t ask if you are seeing others on date one of a first online date and people don’t feel this guilty a month in to a non committed online relationship for a one night stand.  Something is amiss.  My advice is first what is it?  If it’s her issues I am going to say tell her now.  If she has trust issues it’s over if you tell her now or later but that’s not your fault she’s just not ready.  A girl who asks that early on in online dating, the first date is a red flag.

  24. 54

    I think he should tell her, things should be honest from the beginning even if it’s not all rainbows. I’d appreciate the honesty personally and I’d probably be disappointed if I found out later on instead.

  25. 55

    Women are nuts.  Tell her and your relationship will turn into relationshit.  If you want to be happy shut the hell up!  If you want to ruin your relationship and cause all sorts of drama then by all means tell her.  Most men aren’t into soap opera lifestyles.  If you are then you’re probably gay and need to explore that option.

  26. 56

    If she asks you then you should tell her the truth because she deserves to know, otherwise you havent done anything wrong.

  27. 57
    Amy m

    Jason, how has everything ? What happened? Same thing happened with my fiancé Jason (same name) lol I don’t know what to think!

  28. 58

    Please just tell her asap.

  29. 59
    Anonymous Lady

    I can’t speak for other women, but I can say that if I was your girlfriend I would not think you did something wrong, I’d be glad you told me, and I would wholeheartedly ‘forgive’ you the offense (which really isn’t an offense, anyway). I’d be glad you were that open and honest with me. Then again, unlike Evan’s girlfriend, I would also be willing to forgive my man if he cheated on me and came to me on his own feeling bad about it. I’d be hurt and angry and heartbroken, but if he honestly regretted the action, I’d forgive it (depending on specific circumstances). I love my boyfriend enough to forgive him once in a while, and I love him enough to recognize he is human with sexual desires. I also love myself enough to leave if I feel I have been disrespected too greatly or often. Only you know if your girlfriend is this type of woman.

  30. 60

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

    IMHO, it rather depends on how likely she is to find out about it anyway? 😉

    If there is absolutely no chance whatsoever that she’ll ever find out, then I’d keep my gob shut and try to forget about it. However, now you’ve told the Internet about it, the chances of everlasting secrecy may have been somewhat compromised.

    So if there is a chance she might find out about it from other sources, then it’s probably best to fess-up. Only please choose your moment carefully – perhaps when you’re having one of those dreadful “truth sessions” that relationships seem to have from time to time.

    Also try to make a virtue out of necessity – i.e. do it in such a way that it makes you look as if you are a thoroughly decent chap for being so honest – rather than an utter cad for shagging someone else just before you met up. In fact, if you play your cards right, then with a bit of luck, you might even earn a few brownie points out of this. 🙂

Leave a Reply

Your email address will not be published. Required fields are marked *