Thomas talks about: Friends With Past Benefits

By Thomas Whitfield

Although there are a lot of gay men in NYC, it can sometimes be hard to make friends. People here are busy, work hard, play hard and like to have sex. Sometimes past loves become friends, and sometimes friends become loves. Sometimes you keep bumping into an ex that you wish would disappear.

I’ve lived in NYC for five years, and over that time I’ve had sex with a lot of people. I don’t know my exact number. The current guy that I’m seeing isn’t as experienced as me and got upset when he found out that I’ve had sex with one of my best friends. I told him it wasn’t a big deal, we got in a fight, and he said he doesn’t want me to be friends with him anymore. I didn’t tell my boyfriend, but if I didn’t talk to anyone that I’ve had sex with, basically I’d have no friends. Should I tell him or keep it to myself? – Male, Gay, 23

Some boyfriends don’t care if you’re friends with a past hookup, boyfriend or even husband. Others might not even want you to send a “happy birthday” text to someone you once drunkenly kissed. Your boyfriend cares. I think you should tell him, because in the future he’ll probably find out and be more upset. He may respond poorly, but that’s up to him. I would not recommend ending friendships to ease his fears, and for him to suggest that is a control move and very immature. If you were cheating with above mentioned friend, that’s a different story.

My sister is friends with my ex, and it’s driving me crazy. We were together for a couple years, broke up a year ago, and recently my sister mentioned something about him getting a new job. When I asked her how she knew, she told me they talk on the phone about once a week and grab dinner once a month. She acted like it wasn’t a big deal at all, and I got totally mad. She said that I have no reason to be upset, but obviously she knew I would be because she was keeping it from me. She’s basically my best friend, and I’m just like, WTF!? Am I being unreasonable? – Male, Gay, 28

I understand why this bothers you. You’re probably thinking your sister is choosing his side over yours, whatever that might be. It also seems as though she was keeping this from you, knowing you’d be upset. It’s not your place to tell her who she can and can’t be friends with, though. Take some time and think about why it bothers you so much. Are your thoughts rational? Then decide what you do and don’t want to know about their friendship. Tell your sister you don’t want to hear about him, and hopefully she’ll respect that. If you try and demand they don’t be friends, you’re only going to hurt your relationship with her.

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