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

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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40 Comments »Filed Under Cheating, Relationships, Sex, Understanding Men

40 Responses to “I Was Unfaithful to My Girlfriend Before She Was My Girlfriend. Should I Tell Her?”

Steve 1

Jason;
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.
Nadia Shore 2

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.
Henriette 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.
Still Looking 4

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.
Sayanta 5

Agreed. I think you’re over thinking here, Jason.
Lily2 6

Jason;
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!
Eljem 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.
Gem 8

Jason,

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.
Steve 9

@#2, Nadia

Ya-yas?
sarahrahrah! 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!!!
Ruby 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!
Laurie 12

Jason,
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.
Jennifer 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.
kenley 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.
JB 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.
starthrower68 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.
MOE 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.
Angie 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.
50 Proposals 19

I agree with everyone else…until you have the exclusive relationship talk there’s no obligation. She would definitely be happier not knowing.
zann 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.
Fleur 21

I disagree with many of you.

At some point I think Jason has to tell. This is why.

I don’t think this is about this one particular instance, but I think it’s about overall behavior. Disclosure sets the bar for the whole relationship, not just what is happening with them now in this beginning phase. One lie/lack of disclosure can lead to another and another. Coming clean, setting up rules with the new girlfriend, apologizing if it hurt her – these are beneficial types of relationship movement.

For me this is less about blaming Jason for being wrong than about using this as an opportunity for growth in the relationship. He may or may not have been wrong. That would depend on the nuances in their relationship at the time. I’ve started dating someone and had a nice, but not spectacular time, and over time it grew into something stronger. I’ve had other experiences where right at the beginning it was magical and super-connected. Just because we didn’t set up exclusivity rules, if the super-connected guy had fooled around, I would have been crushed and felt his poor judgment was grounds to rethink what I was doing with him. From Jason’s description, I can’t tell where he falls on the spectrum, but honesty and openness is always the best policy in my book. If they had a deep early connection and he blew it by screwing around, the new girl should have the option to rethink what she is doing with him with real information, not just a shell that he thinks looks good on him. If it was casual at the beginning, then if she’s reasonable, I think she will easily let it go. Again, the nuances of their connection should determine the outcome, and if he’s feeling so much guilt, I’m wondering if it began as a more serious and special thing than not.
Jane 22

Cant imagine one good reason for sharing this information ..oops , I just did !
MAYBE Jason and the now – girlfriend had gotten down and dirty on the first date and there was an issue with unsafe sex with the “one nighter” the following night , then back to now -GF thereafter. Is he worried about cross contamination perhaps ???
That might explain the excessive guilt reaction.
Heather 23

Jason,

I don’t think you did anything wrong. You two were not exclusive at the time. I certainly do not tell guys “oh hey, by the way I’m talking to like 3 other guys right now, hope you don’t mind!”. It’s none of their business what I do, just like it’s really none of your girlfriend’s business what you did before you became exclusive. Now, if you’d contracted some kind of STD due to the hookup, then yes, you would have to tell her. But short of that, I’d advise keeping your mouth shut.

We women really don’t want a ton of details about what you’ve done with other women, and more than likely, she might start wondering if you’ve been sleeping around on her since becoming exclusive. What’s done is done. You’re focusing on going forward with her so keep it at that. As the old saying goes, let sleeping dogs lie.
Joe 24

Jason didn’t do anything wrong. Actually, IMO he sounds like a bit of a milquetoast for even considering this to be a problem.
Steve 25

Fleur 21

I disagree with many of you.

At some point I think Jason has to tell. This is why.
I don’t think this is about this one particular instance, but I think it’s about overall behavior.

This would be an excellent point, if Jason’s behavior was wrong. Which it wasn’t. You might as well be worried about establishing patterns of behavior that involve being on time or returning phone calls .
Laura S. 26

It’s obviously a problem for Jason he is unable to resolve in his own heart. This makes Jason one of those rare, genuinely nice men.

If he cannot resolve the guilt on his own without disclosure, and the GF is telling him she trusts him, Jason will begin to pull away from her. The GF, not knowing what IT is, has only her imagination which will create a scenario far worse than the truth. Lack of intimacy kills the potential for a real relationship.

If Jason chooses to reveal his guilty feelings over his pre-relationship indiscretion, he makes himself vulnerable to the girlfriend by showing he is not perfect, he is human. She can embrace the value of Jason, knowing he truly is trustworthy and let him off the hook with his guilt, or she can let the monkeys fly out her butt and start shrieking at him what an asshole he is.

Choosing to disclose leads to deeper trust and intimacy in the relationship, or it ends the relationship because the other person is not who you thought they were. Either way, it’s better for both of them to not try to have a relationship with an elephant sitting between them, and that’s what it is to Jason.
Goldie 27

@ Laura S #26, reading your post made me realize that I really dislike pointless confessions about something that wasn’t wrong in the first place. If Jason tells his GF, that places the ball in her court. He gets to sit back and watch her reaction, (with an added option of judging her on it — “ooh, she’s got monkeys flying out her butt — not good!”), while she struggles to absorb something she’s not comfortable knowing in detail, and wonders why he felt he had to tell her that in the first place — maybe there’s more to the story? otherwise, why tell her about something that happened when she and Jason were still pretty much strangers to each other?

Choosing to disclose puts a LOT of pressure on Jason’s GF and makes Jason look like a well-meaning honest guy who just told the truth. I really don’t see the point in doing it. Like a number of people said on this thread, we already know we aren’t your first woman ever. No need to give us a full list of names, dates, bra sizes etc. That’s too much information.
Androgynous 28

Fleur has a point. If Jason’s relationship with the current girlfriend was still casual and non exclusive after the first date, then why all this guilt ? Most men wouldn’t break a sweat over it let alone eat themselves up emotionally.
Where I differ from Fleur is that there IS a difference between “lying” by omission and straight out lying. I don’t think lying by omission is morally wrong. However, total honesty might be the best policy if the secret was probably going to come anyway, causing your partner to question your integrity. Note the difference between honesty and integrity. While you have been technically honest (you never told a lie and never wronged your partner), you did not have integrity (you did not do what you probably should have done).
The important question here is : Would the girlfriend have wanted to know ? If she does and was going to react badly over something that was not morally wrong (assuming it was clear that his relationship with her after the first date was casual and non committal). The question here is not whether Jason should tell her, but whether Jason should be in a relationship with an emotional basket case at all !
Evan, I think what you jealous ex girlfriend should have said was this “Evan, if you ever feel like going with someone else, please let me know so we can go our separate ways as I don’t want you going with someone else whilst still professing exclusivity with me”. This sounds more rational than something like “I want you to tell me if you cheated so I can dump you”.
Ruby 29

Why are people suggesting that Jason create an issue where none exists? The one-night-stand was just that, one night. Regardless of her specific reaction, the new girlfriend isn’t going to feel great if she’s hears that right after their first magical meeting, Jason had casual sex with another woman. But the sex didn’t mean anything, and there wasn’t a relationship between Jason and his girlfriend yet. If Jason feels guilty, why not channel that guilt into being the best boyfriend he can be for his new girlfriend? Now that’s an action that would have a positive outcome.
kenley 30

Androgynous,

What I have always wondered when I’ve read that story is why Evan’s response was that he’d be forced to lie versus don’t worry I’m not going to cheat on you because if I find myself strongly attracted to some other woman, I will end our relationship. I feel that if you want to cheat doesn’t that mean you don’t really want to be with your boyfriend or girlfriend or at the very least, you have serious problem in the relationship, and doesn’t that mean that the relationship should in fact end?
Ray 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.
Dee 32

I agree. This is coming from a female perspective, you can not violate a commitment that was never made.
Androgynous 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.
Ria 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.
Laura S. 35

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.
Goldie 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.
Laura S. 37

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.
Hope 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.
sthrnphoenix 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.
juan 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.