The Guy that I Like Has Been with Someone I Know

Dear T,

I was introduced to your site by a friend of mine, and really like the advice you’ve been giving. Hope you can give me some that good advice.  My older brother who I honestly thought liked only women, just told me he was bisexual.  As close as we are, I would have never guessed he likes men too. I’m gay btw. So after he came out or whatever, we started talking about his past with men. Long story short, I find out through our conversation that he once smashed the guy I’ve been dating for the past few weeks.  My brother didn’t know I’ve been dating this guy, and this guy doesn’t know who my brother is, so I can’t fault them for anything, but this is weird now.  How do I continue dating someone who my brother smashed?  I didn’t even mention, this guy I’m seeing told me he was a strict top, and my brother told me he smashed him. Could really use your help T in sorting all this out.


Way Too Connected

Dear Way Too Connected,

Thanks for writing to me.  I’m glad your friend turned you onto my site, because I love getting new visitors.  You make sure to tell him thank you on my behalf.  Now as far as your dilemma goes, it’s interesting to say the least.  However, it’s not completely unfamiliar to me.

I’ve often joked with friends how small the gay dating world seems to be.  The saying about “six degrees of separation” has some truth to it. I can recall at least three guys that I’ve dated in the past that I found out later on had some interaction with a new friend or old one.  Having friends say they’ve smashed a potential bae is weird enough, so I can just imagine what that feels like when a brother tells you that.

I’d like to tell you to simply overlook the past or use it as a valid reason to part ways with this guy, but I can’t.  That’s a decision that boils down to your comfort level and how much you like this man you’re dating.  What I will say, is that every person you date will have a history.  Again, given how small the gay community is, there is a likelihood that you will come across people that you really like that have been with someone you know.  That’s a fact.  But if having a sexual history with family members is a deal breaker for you, then by all means, gracefully let the man you’re dating know you two just can’t work. Trust me, most people will understand you not wanting to be with your brother’s former fling.

And let me say this about this guy telling you he is a strict top.  While he may have took on the bottom role for your brother, he may not have enjoyed the experience.  Which honestly is a lot of people’s story. They’ve tried bottoming, realized that’s just not a role they wish to play in the future, and declare they only top.  So in fact, the guy may not have lied to you, but may be a strict top at this point in his life.  In other words, don’t focus too much on his sexual role.

Suggestions going forward.

  1. If you really like this guy you’re dating and want to try to get past this hiccup in your situationship, talk with your brother and this guy about the circumstances of them hooking up. Don’t ask for all the details, because you don’t want that image in your head I’m sure.  However, you should get confirmation from them both that they just hooked up, and neither of them have any feelings for one another. Being caught up in a love triangle, especially with a sibling, is not the business.


  1. Don’t get caught up in the bottom, top, and versatile labels. Too many people spend too much energy into labeling themselves and others.  I truly believe countless folks miss out on opportunities for great relationships, squarely because they focus on these labels. As it was once said in the Dear White People Netflix series, “Labels keep people in Florida from drinking Windex.” LOL!

As always nothing but love,

Tavion Scott

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