Should I tell him I kissed someone else?

I have been dating my fiance for 5 years. During the first 6 months I kissed 4 guys. Each time I was pretty drunk. Now that we are engaged I can’t help feeling awful and guilty now and then. I can’t decide if I should tell him I kissed someone else. I think telling him will hurt him so much and I will only be doing it to make myself feel better. What should I do? To tell or not to tell that is the question.


The real question is to whether or not to let fear hold you back from being authentic.

Many might advise to bury this information and never let it see the light of day. They would ask, “why should you upset him, and make him lose trust in you, just so you can feel less guilty?” Somehow, this model of communication may work to prevent his upset, but it will most likely also create a split in the relationship where you have to keep up a wall. Ultimately, how is that in your best interest — or his?

Your gut is already prompting you to tell. Because you feel guilt and awful, that is already a potential secret wall that will build up between you and the one person in the world with whom you want to be a true closest friend. Being an authentic partner and holding back secrets does not seem to go well together.

Fear holds you back. You do risk upset feelings as a consequence. You do risk a ripple in trust. And that will all be the result of telling the truth, so that nothing hidden stands in the way of the two of you being joined in complete union, as it were.

Withheld information, withheld feelings, withheld anything is like a wall that will only separate the two of you. You can build authentic trust only if you show up in all your authentic honesty. Authentic trust and union does not come from withholding or fear. Sure, you will have to deal with upset feelings. And that is also authentic. But at least it is real and you CAN deal with it — or learn the right tools to deal with it.

The alternative is that slowly building wall — and that for sure will end up being a problem that won’t go away. You cannot pretend your way into a great relationship. You can only face your fears, be authentic, respond to feelings that are real, and learn and grow.