Sex & Dating

Ask a (S)expert: “Should I Tell My Partner I’ve Cheated in the Past?”

Welcome to our new series led by Gigi Fong, Hypebae’s in-house sex and dating editor.

3,553 Hypes

Ask a (S)expert: “Should I Tell My Partner I’ve Cheated in the Past?”

Welcome to our new series led by Gigi Fong, Hypebae’s in-house sex and dating editor.

Welcome to your new safe space and Hypebae’s first-ever sex and dating column, Ask a (S)expertThis new weekly series is led by Haitian-Chinese and LA-based sexpert Gigi Fong, our in-house sex and dating editor.

Gigi is a former sex worker, boudoir artist and podcaster now hosting safe spaces for the Hypebae community. She specializes in all things sex-positive from unconventional dating to pleasure for lovers of all identities. To have your questions answered, visit our dropbox below and anonymously send your intimate inquiries ♡


“Does your partner need to know your sexual past/the actions you have done in the past? I’ve been dating my boyfriend for 4 years but he doesn’t know that I fucked my ex’s little brother (he was a year younger than me) when he became a freshmen at my college. I know, super fucked up. It wasn’t supposed to happen but drinking will do that. But now I think about what happened and debate whether telling my boyfriend is the right thing.”

Hey bae! Okay, first, welcome to our safe space! Societal norms can place a lot of pressure on us so I understand the pressure you feel.

In a broad sense, yes, you should discuss your history with your partner for sexual wellness and pleasure purposes. On the pleasure front, discussing favorite sex positions or memories like when you had your first orgasm is great. This allows you to build intimacy, create that safe space for communication and f-ck each other better. Of course, on the sexual wellness front, it’s important to be open and honest about anything that could affect your dynamic like an illness or any risky behavior.

In your case, it seems like you’re feeling feelings of shame and questioning whether your partner will judge you. Considering most people look at history to determine how they’ll be treated, it makes sense. But from what you’ve shared, you regret that past experience and don’t see yourself aligning with that behavior in the future.

Most relationship experts would advise for total honesty, especially if it’s already weighing on your mind. The reason being, if it’s weighing on your mind and you’re not addressing it with your partner, it’s probably already flared somewhere else in your relationship subconsciously.

Discussing your sexual history with your partner opens a world of pleasure for both of you. But, it can also spark feelings of jealousy and anger. It seems that to you, this story in particular isn’t essential to the foundation of your relationship, as you no longer identify with that behavior. But if you want a dynamic built on pure and total honesty, maybe you should consider telling your partner before that fear and anxiety flare elsewhere within your dynamic.

Good luck!

For more sex and dating advice, visit Ask a (S)expert.

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