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Advice – Should I tell my girlfriend I slept with other people while we were on a break?

For clarification; we’ve been dating on and off for about 8 years and she is my best friend.

A couple of years ago we had a year or so apart, she broke up with me. We still had some same friends so we saw each other around on and off through that time and around a year or so later we got back together and are together still. We are as strong as we’ve ever been and there is no immaturity about it all.

In our time apart I did what any newly single person would do and had fun, met up with people and had a few drunken ONS. But I never mentioned it to her, as we were not together ofc. And haven’t since then, I didn’t bring it up when we got back together.

However, in a jokey game recently with friends where we had to answer questions about each other to see how well we knew each other, the number of people each of us has slept with came up. I didn’t correct her number she gave me, mostly because I didn’t want the first time she hear about it to be in front of friends, when were having fun etc.

It has played on my mind a bit all this time. The line between being honest and being too honest.

Would bringing it up, long after the fact, be pointless?

Or would her finding out through other means, and me having not told her, be worse?

Anonymous, Reddit.
Photo by Vee O on Unsplash

Dear Anonymous,

I understand your initial decision not to tell your girlfriend about who you slept with in the year apart. It is possible that you didn’t feel the need to disclose how many partners you slept with for couple different reasons. The safe and obvious assumption from when you were apart from your girlfriend is that both you and your girlfriend found others to meet your sexual needs for that year. In addition, you might not have been emotionally prepared to hear how many people she slept with while on break, even if you operated under the assumption that you both slept with others.

Your recent decision to not correct your girlfriend also makes sense. Not only would it have been incredibly humiliating in that specific circumstance, I agree with you that it would not have been a safe place to openly talk about vulnerable topics. This in turn explains the retrospective ambivalence and guilt you feel about not being upfront about your sex life during the break. This current ambivalence and guilt stems from the initial decision to not share, because at least a small part of you believed that you should have shared.

As you pointed out, there is a very fine line to toe between being honest enough and being honest to a fault. And the thing is, that fine line varies wildly between person to person. There is no universal morality around when or if you should talk about your previous sexual history with your partner because it greatly depends on your overall comfort level as it pertains to discussing previous sexual experiences, the context of that discussion, and your personal intention leading to that conversation.

Photo by Nashad Abdu on Unsplash

Another wrinkle in this circumstance is your intentions.

If you sit back and reflect on why you want to share your sexual history during the break, you might find that the inherent ambivalence flows deeper into each of those possible intentions.

If your intention is that open and honest communication should be always be exercised, then you might find yourself contending with the decision you’ve already made not to share. The difference here is clear. Timing is all different. You might not have known back when you got back together that you would continue to stay together. And for those couple years, you were able to build upon the baseline of trust that you had before you two decided to went on a break. And so, because the context of your decision back then was different from the context of your decision now, this decision need not be the same.

Your intention could also be brewed with the desire to gain control over the narrative of your own sexual history. Built into the initial assumption of sexual activity during break are two separate foundational beliefs. The first belief is that you and your girlfriend were on the same page about your respective sexual activity during the break. The second belief is that you and your girlfriend would each inform the other any aspects of your sexual history without each other, if it was deemed relevant. As such, your desire to correct the wrong comes from a deeper place where you want your girlfriend to live in the same reality as you do. That is both fair and sound.

However, if your only intention is that revealing the full extent of your sexual history will alleviate your feelings of guilt, then that is neither a compassionate nor safe way to approach this revelation for your girlfriend. After all, your girlfriend could find her anxiety and insecurity triggered to hear that she wasn’t exactly on the same page as you for the past couple years.

What is the ongoing price of admission that you are willing to pay to keep this hidden from your partner?

Your decision will also have to reflect your girlfriend’s headspace.

How has she handled learning about your sexual history or general sexuality in the past? If the overarching modus operandi regarding sexual history in your relationship has been a more of a Don’t-Ask-Don’t-Tell approach, then the risk of unknown and the risk of negative reaction greatly outweighs the overall benefit of alleviating your guilt and true honesty about the past. However, if she has taken talks about your and her sexual history well in the past, then this conversation could absolutely be an opportunity for you and your girlfriend to connect deeper as a couple and as individuals.

I sometimes jot down my own thoughts down on paper (or screen) as a way to have a dialogue with myself over complex decisions. On paper, my idealistic self would outline all the good a potential decision might bring. Then I would sit back and talk back in person to my idealistic self all of my worries and fears about that decision. And this back and forth would go on until I decide that either:

  1. The overall goodness of the decision outweighs the possible badness, at which point I push ahead with my decision.
  2. The possible badness of the decisions outweighs the overall goodness, at which point I take time to grieve through the decisions unmade.

My two cents: take this opportunity to develop yourself or your relationship. If that means sharing this very vulnerable and neglected part of your past history, then use that momentum to share why this felt so vulnerable to share and connect deeper with your girlfriend to explore other vulnerable spaces. Even if this doesn’t go well, you can still use this as a learning lesson for yourself on the boundaries of your and her fine lines on honesty.

Good luck!

Tea Time with Tomato is an informative relationship and sex advice column for both monogamous and polyamorous folks. By submitting your post, you agree to let me use your story in part or in full. You also agree to let me edit or elaborate for clarity.

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