Thomas talks about: Guessing Games

By Thomas Whitfield

I have a straight best friend that I met in college, and up until two months ago he’s never given me any inclination that he’s gay. One night we were hanging at my apartment, having a few drinks, and he made a joke about kissing me. Then, he leaned over and did it. We both laughed, no big deal. But then he started to kiss me again, and we ended up making out for a long time. We hung out the following week, and neither of us mentioned it. Then like a week after that and we made out again; he initiated it. It’s been back and forth like this, and now we’ve made out four times. I don’t know if I want it to go further… he’s my best friend, but I don’t think I’d want to “date” him, and IDK if he’s even gay. -Male, Gay, 28

The issue here isn’t about if he is or isn’t “gay,” it’s that you keep making out but not talking about it. You don’t know where either of you stand on what’s going on. Acknowledge the situation (while you’re not drinking). He might tell you that he has feelings for you, he’s just having fun, he thinks he’s gay or maybe he’s curious and feels safe with you. Then be honest with him about how you feel. Do you want it to continue? Under what circumstances (i.e., just fun, dating, friends with benefits)?

I’ve been hooking up with a guy from an app for the last month, and after we hung out last he mentioned he’s married to a woman and has a couple kids. I realize this isn’t completely unheard of, but I wasn’t expecting it, and he could see it on my face. He told me that he loves his wife and would never leave her, but that he also “loves dick so much.” As far as I know, this the first time I’ve had sex with a married guy, and I feel EXTREMELY guilty about it. Am I responsible for his cheating? I keep thinking about what might happen if his kids found out. I like the sex, but maybe I shouldn’t do it anymore with him? -Male, Gay, 37

At the end of the day, you’re not responsible for anyone else’s actions. With that said, a lot of guys could be in your situation and not care, but you do, and that’s OK. Because you’re concerned, and this is NYC, I’d recommend just finding someone else to have sex with. There are probably dozens of guys within blocks of you that would be willing to have sex, so if you’re just looking for sex, go with your other options. It seems like the situation with the current guy could potentially become a lot of drama, and if deep emotions aren’t involved, is it worth it? Probably not.

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