Sex & Dating

Ask a (S)expert: “I Thought He Knew But... Turns Out He Didn’t Know I F-cked His Brother”

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

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Ask a (S)expert: “I Thought He Knew But... Turns Out He Didn’t Know I F-cked His Brother”

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 ♡


“I’ve had sex with two brothers. 

The younger one I met a year ago. He walked past me in a club and said ‘You’re gorgeous.’ I searched for his Instagram and then we went on a date, came back to mine, had sex… lasted less than a minute, and didn’t really speak after that.

Years later, we went on a more formal date, actually spoke more and I left him on the tube, and said ‘This is your stop right?’ But he thought he was coming back to mine. I went home, he then texted me like ‘I wanna come round.’ I gave in and he came, had sex again, didn’t really speak. The point is there are no feelings. 

Anyway, I went to a festival and saw his older brother. He walked past me and said ‘You’re beautiful.’ I said, ‘I know your brother.’ He said ‘How well?’ I said ‘Well enough.’ So I assumed he knew I slept with him. We ended up spending the WHOLE weekend together, getting along so well, having a crazy connection, planning holidays and meeting up in London. He spent his whole weekend with me rather than with any of his mates. He introduced me to all of his friends and we all got along so well. He couldn’t believe that all of his mates liked me — loved me — which was a bonus. I’ve basically never had a connection like this with someone.

In the last few hours, he asked me if I slept with his brother, and I said yes. His head was spun and I was crying, saying I can’t change the past. etc. Is he more worried about his ego? The outcome is I really like him and I’m not bothered about his brother. I don’t even remember him. But I really like his older brother and I don’t know where I stand with him. Is it going to be awkward? Will he see past this? He wants me to go to London and see him but I don’t know if he wants sex or agrees with our connection (I know he does but I’m unsure about the younger brother, he has a gf he doesn’t care).”

Hey bae! Okay first of all, this family and the “You’re beautiful line” is sending me. This is admittedly very layered. Although it may feel like no big deal that you f-cked his brother, people vary on the open-mindedness spectrum so it’s important to weigh a few factors.

If you’re a Love Island stan, this reminds me of an episode where Ty and Ella go to Casa Amor, a place to take space from your lover and at the end, decide if you’ll recouple with a new man, or remain with your true beau. Ella recoupled and came back with another boy, while Ty chose to remain single and wait for Ella. Ty eventually takes Ella back, but viewers worldwide couldn’t help but think “Girl, NO.” Why? An emotionally immature man will patiently wait to get his lick back, or in other terms, get revenge.

From the sounds of it, you’ve both begun investing in each other’s lives from friends to unintentionally… family.  So most importantly, I ask: how emotionally mature is he? If he’s emotionally mature, as in he can effectively communicate his feelings and practice conflict resolution, this is definitely worth working on. It’s also important to ask yourself if you are willing and able to be around his family knowing you’ve been involved with his brother.

You need to sit down and have an initial conversation about how you both feel, as well as, what you’d like the relationship to look like moving forward. Will you attend family gatherings? Do you need to find a couples therapist to help manage triggers along the way? Is he more concerned about his pride, or future with you? If you’re unsure about the size of his ego, attempting to resolve this conflict will reveal everything you need to know. From whether he can handle his emotions to effectively communicating them to being receptive to your reassurance. If he can’t, the relationship is doomed — and that’s whether you had f-cked the brother or not.

Trust me, it’ll be difficult as it’ll bring up heavy emotions. Investing in a therapist may be essential to guide those difficult conversations. Keep in mind though, that he can absolutely decline to move forward and that’s valid, too.

Wish you the best, bae!

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