Ask Chad

Hey Lovelorn Subordinate!

Good for you, girl. Hookin’ up with the boss is always hot, especially when it happens at work. You are clearly writing the wrong person because I’ve been fucking without feelings since the first Gossip Girl was on TV.  But how to explain to someone else how to turn feelings off?  Start with texting other guys, go on the apps. Even if you don’t bang, at least you won’t been totally hung up on your married boss. You’ll feel desirable to other guys and it will help look at this guy as just one instead of the one. Like he’s married, so clearly this is limited. Enjoy it, get some good work perks, and then bounce onto the next D.

Hi Gay Loner,

I am all about embracing change. Change your hair, change your address, change your OnlyFans lighting and angles. Finding friends can be hard. You didn’t mention being sober and sober people always do, so you could go to bars during the day or early happy hour when everyone’s chatty. Go to an underwear night (like VPL in LA), there’s no faster way to make friends than showing off your bulge and cakes. You could join a gay sports league if that’s your jam. They have everything from football to bowling. Start being friendly to gay people you interact with on the regular, soon you’ll follow on social, then make plans to hang and bam, friends. Basically put yourself out there. And don’t go on Grindr. No one is actually looking for friends on Grindr.

Hooking up with your friend’s man, a tale as old as time. That what Mrs. Poppers would sing about as a bear and twink slow danced. Now, this is very dangerous because even if your friend is oblivious to the sexual tension, your other friends might not be. You don’t need a single glance or touch clocked by the crew. So what to do? I would back out. Come up with an excuse of why you can’t go. Don’t put yourself in a situation where you’ll have anxiety the whole time. Now if you guys are done banging by then, go and have fun. But as long as there’s a secret simmering below the surface, you danger girl.

Well girl, the breaking into the phone is like pooping. We all do it, no one should talk about it, especially not in depth, it will ruin your relationship. Now that said, porn is fantasy. While you were going through his phone, did you find anyone he was planning to act these kinks out with? If the answer is no, slow your roll. Now, you can’t admit to going through his phone, but maybe put the blame on yourself. Say, “I’m feeling in a sexual rut, let’s try and explore some new stuff.” Then each of you take turns sharing new kinks that might turn you on. That way you open the door without having to confess to the crime.

Oh man, what an opportunity. You’ve got to hit it!! How could you not?! The chance to fuck your first but with the wisdom of knowing what kinks you each like and how to properly suck dick and eat ass? How could you pass that up? Do it for all of us who wish we could. Just message him something casual like, “Welcome back, let’s get together and rehash old times” or if you’re feeling bold something like, “Is that dick as big as I remember or was it just youth?”

This goes back to that age old cliché about open relationships… The reality is it’s so hard to not fall for someone when you connect with them on another level. We’re such poly creatures (especially us gays), it seems natural that you’d love the one you’re invested in this relationship with but also this new person with whom you feel deeply. #LoveIsLove. Now the question becomes will the current BF let you explore this? Could you throuple up? Is there any scenario where you could you have both—an and instead of an or? Relationships are evolving. If you guys connect in such a real way, there’s a reason why. Isn’t that worth exploring too? Only you can carve out the life you want for yourself.

Listen, dear, if you don’t list a problem, how can I help? Kidding. But for real, who cares? You like group sex, who doesn’t?!? It sounds like you’re single, so you do you! Have fun with as many men as you want. Now, if you have a man, then some convos have to be had. But also, find a man who likes group sex as much as you, and you boys can always host.

Guuurl. You’re not ready. Like a bottom who says, “I know my body.” You want your ex, and that’s obvious. Nothing wrong with wanting an ex. We all do it. EVERYONE USES SOCIAL MEDIA TO STALK THEIR EXES. Let’s be all the way real right now. It’s not fair to the new guy, so cut him loose, and work it out with the ex. Unless he dumped you and moved on, in which case, you’re screwed. But if he’s texting you nonstop, he clearly wants it too.

I’m sorry I’m still coming down from Friday. Did I read this right? You’re complaining you’re getting too many sexts from some guy you work with that you also bang? Girl bye. When I worked retail, the photos I’d send co-workers from the dressing room were some of my best all-time nudes. Why cross the line to fuck buddies if you wanted to keep your girlfriend? Or you’re a greedy bitch and you wanted to have his cake and eat it too. If you’re really tired of it, stop responding. Just like it with emojis, no text needed. He’ll get the hint. No one sends hole for a thumbs up.

As someone who has bailed on many a trip with guys I’m no longer interested in or Daddies who booked me in coach, let me tell you, there’s two ways of doing this. One, a classic, blame your tummy. No gay that still wants to fuck you is going to ask too many questions. “Tummy trouble. Can’t risk it, not feeling it. Sorry.” Xo Gossip Boy. The other option is be a little honest but frame it like you’re doing him the favor. “Babe, I don’t want to take you away from your friends during this big weekend. Go just enjoy them and not worry about if I’m having fun. You just live it up, and I’ll be home and douched when you get back.” This way, you come off looking so generous…and you still don’t have to go.