I Kissed. Should I Tell?

Dear Em and Lil,

I have been dating my boyfriend for less than a year, and things are going well. We like spending time together, share common interests and enjoy socializing. About four years ago, long before meeting my boyfriend, I made out with one of my friends. Do I need to tell my boyfriend about this history or is it ok to let bygones be bygones?

-Coming Clean

LIL: Let me start by saying I don’t think it’s a big deal that you made out with your friend four years ago. But I’m also aware that your boyfriend may feel differently about this. Some people believe that you can’t be friends with your exes, or anyone you’ve hooked up with or dated in the past. Some people think that men and women— or more generally, any two people who could be romantically tempted by each other— are incapable of staying just friends and will eventually rip each other’s clothes off. Is your boyfriend one of these people? Or, has he either shown or told you that he has a tendency to get jealous?

If your answer is yes to any of this— and you and this friend are still close and spending time together— then I think you should tell him. That might seem like a catch 22, so let me explain. If you and your boyfriend have a fundamental difference of opinion about who can be friends, at some point you will need to hash it out. And during that discussion, you don’t want to go out of your way to avoid mentioning this friend because it’s become a big secret. You want to be able to have an honest conversation. Plus, in itself, keeping a secret can make you feel guilty, and there’s no need to feel guilty about what happened with your friend. The longer it takes to tell your boyfriend, the bigger it will seem to him if he ever does find out. And it could even become a trump card for unrelated situations: “well, you didn’t tell me about kissing Gregula, so how do I know you don’t have other secrets?”

So, if you think it will be a big deal to your boyfriend, how should you bring it up? Make it a conversation about boundaries. Ask him to explain what makes him jealous, and to spend some time thinking about why that’s his instinctual reaction. Knowing what sets off those feelings could be helpful to you— there might be small things you’ve never considered that you’re perfectly happy to avoid. Then it’s your turn. You don’t want to hurt your boyfriend, but your boundary is that you’re not willing to end a friendship because he might get jealous. Use Gregula as an example. You know friendships with a spoonful of history can work, because you’ve had one for four years. You can discuss compromises that might make him feel more comfortable with your continued friendship, as long as it’s with the understanding that he will work on his trust. This will be beneficial to him as well as you. Feeling jealous or distrustful of your partner is hard on you and hard on a relationship, and learning to talk back to those feelings when they come up can be super freeing. If both of you are able to approach this as a brainstorm, and not shoot each other’s feelings down right away, neither of you will feel like you are giving anything up.

EM: I don’t think that you need to tell. Before getting together, you and your boyfriend lived separate lives. You did separate activities, dated separate people and shared occasional smooches separately. Your boyfriend likely knows the arc of your relationship history, and I think you can spare him the details. Divulging unnecessary information could do more to make him uncomfortable than help you grow your relationship.

I suspect your motives here are a bit misguided. I think that you think you want to come clean and be honest. But might you subconsciously be trying to get a rise out of your boyfriend? No judgement here. My younger, shittier self had the occasional (fine, more than occasional) desire to make my significant other jealous. By prompting a tantrum in someone else, I was able to get the attention and validation I was looking for. I was a giant four year old who settled for getting ‘bad attention’ when I failed to get ‘good attention.’ So, Coming Clean, ask yourself if you are truly trying to clear the air, or if you are trying to manufacture a fight with your boyfriend. 

Avoiding an overshare is not the same as lying. In this circumstance, skipping the weird confession is the chillest and classiest way to move forward.

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