By Jessica Lanyadoo

Hey Jessica,
I have had a patchy, promiscuous past in my relationship history. I’ve been a cheater, I’ve had multiple fuck buddies at once, I’ve said I love you only to break up six months later, the works.
Currently, I’m living with an amazing guy who I’ve been with for just under a year. I feel totally different about this one — no feelings of restlessness that I’ve had in past relationships. He might not be “the one,” but it’s still feeling really, really good.
My question is: should he be privy to my rough past? I’d like to not damage my relationship by telling him I’ve cheated, but it sort of feels like I’m lying to him by not telling him, even though these things never directly come up. I want to be open with him, but should I just let the past live and let die?
Sincerely,
Dark Past
We’ve all done stuff in relationships that we’re not proud of, and there are definite pros and cons to dredging up the past when the present is going so well. Making peace with your past is the real goal (as opposed to killing it off), DP, ’cause it never really dies; it can’t because it lives on inside of us, shaping our reactions, our attitudes, our hopes, and our fears.
Excuse this digression, but I’ve gotta ask: did you lie to your fuck buddies and lead them to believe that they were more to you than just hook ups? ’Cause my understanding of a fuck buddy is that there are no obligations, and you can have as many as you like, no harm, no foul. And when you told people in your past that you loved them did you know that you really didn’t? Did you intentionally screw with them, or did you think you meant it when you said it? Because as much as cheating sucks, the other stuff you mentioned doesn’t sound that bad, unless you lied your buns off in those situations. It just sounds to me like you’ve had a lot more sex then love, and that doesn’t make you a bad person, DP. Separate from answering your question, I encourage you to parse out what you did that was so bad from what you have judgments about ’cause they’re very different things. Promiscuity is only a bad thing if you acted out of integrity when you did it, which is a personal assessment. So a little more contemplation of your actions might get you some peace with yourself.
If your relationship is going to fail or falter, don’t let it be because you held back the messy bits of your past, or because you’ve been acting weird from the guilt of keeping secrets. Real relationships are based on realness. You don’t have to tell him everything you’ve ever done, but it would be so much better for you if you stopped avoiding telling him the truth.
Now on to your Q: I say tell him. If you want this relationship to move forward, you have to get this off your chest. It’s not about right or wrong, (although a case could be made for either), but you obviously feel bad for omitting this information about your history. If your relationship is going to fail or falter, don’t let it be because you held back the messy bits of your past, or because you’ve been acting weird from the guilt of keeping secrets. He’s entitled to whatever reaction he has, and he may not really care. It might make him trust you a little less, or he may have a million reactions in between, but that’s OK. Real relationships are based on realness. You don’t have to tell him everything you’ve ever done, but it would be so much better for you if you stopped avoiding telling him the truth.
It’s only fair that you think about why you cheated before you open this can of worms, though, DP. Be prepared to let him know how you are different, not just your situation. The problem with cheating is that it’s generally either weak ass behavior from a person who doesn’t know how to deal directly, or there’s a sense of entitlement governing one’s actions. If you want to stay monogamous with your sweetie and share your heart with him, I encourage you to share the good, the bad, and the ugly of it, and give him a chance to love all of you.
XO,
Jessica
The Mission’s resident advisor gets booked months in advance by San Franciscans seeking help with all kinds of relationship issues. So we asked Jessica if she’d come on board to do a weekly advice column, Truth Talk, for The Bold Italic. If you have a burning question for Truth Talk with Jessica Lanyadoo, you can post your question anonymously here or email her at truthtalkwithjessica@gmail.com, and check back on Wednesdays to see if she has an answer for you.
