Thomas talks about: Your Best Friend’s Brother

By Thomas Whitfield

I always laugh when I hear gay guys make comments about how they want to date a “straight guy.” Mostly, I laugh because I grew up in the Midwest surrounded by “straight guys,” and they’re not the same ones you see in movies. I do wonder how much of the attraction has to do with the idea of being the “first” or “only” to the “straight” person, thus leading to a feeling of being special. Either way, most of us know of a “straight hot brother,” and y’all got stories.

Last weekend I went a beach house in Jersey with my best friend to stay with his family. One night his hot “straight” brother and I stayed up chatting, and then eventually I went to sleep on the living room couch. A few hours later, he woke me up with his hard on in my face. Of course, we hooked up. I don’t want anything with his brother, but should I tell my friend?
– Male, Gay, 23

Congrats on living the plotline of a porno—we’re all very jealous and a little turned on. No, I don’t think you should tell your friend unless you have a real reason to—and it doesn’t sound like you do. Most people don’t want to hear about their family members hooking up, even if it’s their attractive brother. Your friend probably doesn’t view him as hot. Also, you don’t know his brother’s story, and there is no reason for you to “out” him, especially if you don’t want to pursue anything with him. I say keep it for your spank bank or the next time you visit his family. No reason to start drama.

My best friend and his brother share an apartment in HK, and there’s a running joke that his brother is gay. Honestly, I think he might be, or at least curious. Also, if he is, I’d love to break him in, ya know what I mean? Sometimes he jokes back with us about being gay, but I can’t tell if he’s flirting or just comfortable. Any tips on how I can tell if his brother is gay? – Male, Gay, 22

Read the above question, and wait for him to wake you up with his hard on.

Just kidding, obviously. It’s funny, because when you’re in your 20s, I think you spend a lot more time trying to figure out each other’s sexuality, whereas when you’re a bit older, it just becomes too much work and energy to care. I understand the curiosity, but you can also rest assured that if he wants you to know he’s gay—especially if he wants to have sex with you—he’s going to make it clear. When, if ever, has one gay guy said to another, “I wanted to have sex with you, but I just didn’t know how to tell you”? If anything, it’s more so, “OK, I get the point, you want to fuck?” His brother sounds like a nice guy, so the best way to find out is probably not to have an agenda and attempt to be his genuine friend.

Sex/Love/Relationship advice? Send your questions to: [email protected] Instagram: @ThomasWhitfield84