I am dating a guy, we are totally in love, and this past weekend we took the major step of visiting his parents. We get to the house after he has prepped me about how the parental unit can be a little conservative, and we go inside to meet them – and I am faced with a man that I have definitely had sex with quite a few time when he was ‘in town on business.’ Yeah, totally hooked up with my boyfriend’s dad (before we got together, of course). So, I’m sitting on this huge bombshell, and I don’t know if I should keep quiet or tell my boyfriend because not saying anything feels like I’m betraying him. Help me, what do I do now?

A

Talk about having the past come to haunt you! The unfortunate and quite sad thing is that this bombshell could have potentially devastating consequences for you – and all you did was hook up with someone unknowing that he was under the radar. Here’s the thing: You say you are very much in love, and you are taking next and important steps to deepen your connection. On one hand, you could stick your head in the sand and pretend this was all in the past. A little white lie like this could your relationship and potentially your boyfriend’s family a lot of conflict. On the other hand, it will be difficult for you to enter this next phase in your relationship, especially since you are taking those big committal steps. Maybe you can feel out the vibe of the family a little bit more – who knows, maybe the whole family is super sexually open-minded and in on the secret! But for now, keep this under wraps under the guise of ‘we all have a past,’ and even his father deserves the discretion he used with you. Now, if he starts approaching you again for sex, that would be your cue to come clean to your boyfriend. 

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