Dear Dad: Should I Have Sex With My Friends?

Dear Dad

What’s the best way to friendzone someone you’ve been hooking up with?

—In the zone

In the Zone,

Befriending a hook-up is a noble and worthy cause, like using metal straws or putting the “coexsist” bumper sticker on your car. One clear way to let a gay male know that you’re not attracted to him is to call him “girl” or “sis.” You know what I mean, gal? The minute a tall drink of water calls me “girl” my eyes start darting around the room seeking my next victim. You could also show him pics of guys you want to fuck. Not exactly the gentlest way, but he’ll definitely get the picture. Once he realizes you’re on to greener pastures, hopefully he can get on board and you can be gal pals to the end of your days.

My dad’s best friend and I have been flirting for two months, is it cool to have sex with him?

—Daddy’s boy

Daddy’s Boy,

Hey, isn’t this the setup to the last CockyBoys video? Ya know, this week’s theme was meant to be about having sex with your friends, but this is too good to pass up. As a man of a certain age, the thought of my kid sleeping with one of my friends makes me want to die. However, I am aware that boys will be boys. If you feel safe and you don’t think your father will find out, why not? Better yet, if you’ve got an open and honest relationship with your father, why not just ask for his blessing? My only caveat is that if your father is a gay male and he’s slept with this man before, absolutely no. That would just be weird.

My friend and I recently hooked up and I’m have feelings for him, but I’m scared about ruining our friendship. What should I do?

—Friend or more

Friend or More,

I get this question a lot. People are always worried about exploring relationships with friends, mostly because they’re worried it could potentially ruin the friendship, but also because, in my opinion, they know it could lead somewhere fantastic. I think fearing a friendship will be “ruined” is a tad misguided. Relationships evolve; if your relationship with a friend is evolving into something more, something deeper, that’s a beautiful thing. After the romance fades, when you’ve explored your sex life to the furthest reaches of the universe and the honeymoon period has faded into the distant horizon, what you’re left with is friendship. Starting from a place of friendship is like having the strongest foundation possible for a relationship. Don’t pass up the chance to explore out of fear. If you really believe you have feelings for them, reach out and touch...something. You never know what’s waiting on the other side of friendship.

My best friend just slept with my bf (we’re open) but didn’t tell me. How can I approach him about it?

—Prickly Sitch

Prickly Sitch,

I’m so bummed to hear about this situation. Obviously if he was a true friend he would have asked you before engaging in sexual relations with your bf. And then there’s your bf—I can’t imagine that him having sex with your best friend was ever on the table? This is a prickly situation and I’m sure you’re feeling upset and reactive, but keep your wits about you so you don’t make the situation worse for yourself. Talk to both parties and see what happened. Was it a drunken mistake? A stupid crush? It’s best to find out specifically what’s going on. If it was a mistake that they both regret, then you need to decide if you have it in you to forgive and move on. If it is something else, or part of a bigger pattern, then this might be a good time to re-download Grindr.