This post is also available in: Español
Dating Is a Drag! 14 Queens Share Their Personal Tips and Horror Stories
As gay men, we’ve all got ’em: dating horror stories. And sometimes, if we’re really lucky, it’s a horror story that happened on Valentine’s Day to boot!
But here to share some of their favorite V-Day and general dating horror stories — plus a few dating tips, for those who may need love life assistance — are some of our favorite drag queens.
From coast to coast, these drag performers have pretty much seen it all, so let them regale you with their wise words.
Just in time for Valentine’s Day, here are 14 drag queens with dating tips and personal horror stories:
1. A story from Peaches Christ
Back when I was a single gay first dabbling in the world of online hookups, I invited a guy over to my place one lonely Valentine’s Day to fool around. This was before social media really took off, and so most people locally didn’t know what I looked like out of drag. It was easy to be anonymous.
So he comes over and we had a lot of fun for a couple hours, and after he put his clothes back on, as he’s leaving, he sees a poster of Peaches Christ on my fridge. He says, “I love Peaches Christ! You’re a fan?” and in that moment I had to make a quick decision, so I just say, “Yeah.”
He then goes on to say, “She’s crazy. She blew my friend on the back of the Trannyshack Reno bus …” and I’m like, “Uhhh, no, that never happened.” As I usher him to the door, he starts arguing with me. I’m insistent that his story is untrue, and he says, “Are you calling my friend a liar? How do you know it didn’t happen?”
At this point he’s standing on the other side of my door, and I muster my best Joan Crawford/Peaches Christ voice and say, “Well, my dear, I know your friend was never blown by Peaches Christ, because you were just blown by Peaches Christ!” His mouth dropped open, and I slammed and locked the door.
He wrote me later and apologized and asked if we could meet up again. We did, but somehow it wasn’t as hot. There was never a love connection, but at least I got a fun story out of it.
Follow Peaches Christ on Facebook here.
2. A dating tip from Alaska Thunderfuck
Get used to hair. And I don’t mean back hair. I mean wig hair. If you’re dating a drag queen, wig hair will clog your drains and collect in the corners of your home from now until the end of time.
3. A story from Ambrosia Salad
So, though I have a few entertaining stories about sexual encounters while in drag, they’re mostly too long and explicit. However, one comes to mind that is short and sweet and left me feeling like a bag of dirty used-up eyelashes.
Around six years ago, when I still lived in San Francisco, I had just finished performing at The Supper Club and went to an after-party thrown by the Radical Faeries. It was a very sex-positive party. I’d had my fair share of drinks and a little recreational drug usage and was feeling rather frisky. I was wearing a little mini white dress and a honey-blonde wig.
I spotted a cute little bear cub couple who I had never seen before in the corner getting rather touchy with each other, and I decided to approach the little escapade. I don’t remember my exact words, but they were definitely along the lines of a proposition.
Cut to 20 minutes later, as I rose from this dark and steamy corner — hair frizzed and messy, makeup smeared, tights torn. I began to make my way back to the rest of the party when the couple, almost in unison, shouted out, “THANKS AMBROSIA!”
I stopped in my tracks and cringed as those words hit my back like an unexpected load. A few people at the party turned to look and gave a giggle. I proceeded straight to the front door and called a cab. I guessed my duties for the night were done.
To this day, my friends who know the story and wanna get a cringe out of me still love to say, “THANKS AMBROSIA!”
Find Ambrosia as her alter-ego, DJ Sindri, at parties No Nonsense L.A. and Featurette.
4. A dating tip for Valentine’s Day from Sarah Problem
Looking for the perfect gift for your sweetie this Valentine’s Day? Skip the typical box of chocolates and make her a Strawberry Shortcake. A Strawberry Shortcake is where you cum on her face and then punch her in the nose till it bleeds. Tada! Romance.
Follow Sarah Problem on Instagram
5. Some real dating advice from The Boulet Brothers
We’re excited to have the opportunity to talk to our fellow queers about relationships! Being that we are two men who have been together for a very long time, I think we’ve learned some things along the road that other guys might find helpful when looking for a partner, or how to stand the test of time with a partner they already have.
For starters, when you’re first dating we think it’s important to be honest about everything. Lay it out on the table. What kind of sex do you like? What are your relationship goals? What are your career goals? A lot of guys tend to put up a certain front to make themselves more desirable in the beginning, but if you’re not being honest about what will make you happy, the chances of those needs being met (if a relationship develops) are slim to none.
Once you’re in a relationship, things get trickier for gay men, and a big challenge is other men. Comparing yourself or your partner to other men, questioning if you want to (or should) sleep with other men and navigating how you both feel about all that can be tricky. Whether you choose to be monogamous or have a completely open sexual relationship, there are so many arrangements out there for gay couples that can work, and it can be a bit confusing when you’re starting out. We’ve seen it all work, so there is no one way to do it, but in our opinion there is one rule you have to follow regardless of what your arrangement is: your primary partner needs to be the sun in your universe. He needs to be the one you truly love; he needs to be the priority, and anyone else should be nowhere near as valuable as your man is, whether it’s sexually, emotionally or physically. Your partner should never have to question if the next guy has something you may want more than what he has.
Also, while all of these different arrangements can work, we seriously suggest being monogamous for a long time before you even consider opening up your relationship. You have to build a solid steel bond of trust and love between each other. Your partner needs to know and feel that he can trust you 100% and that you are nothing but honest, loving and trustworthy before either of you consider other options. On that same note, some gay men are uncomfortable with even mentioning open relationships, but classic monogamous hetero normal relationships are not universally fulfilling for all gay men, whether you like it or not. In our travels, we’ve seen guys in queer puppy packs in San Francisco that are completely fulfilled and just as happy as some of our monogamous friends who are couples. It all comes down to being a stand-up, honest, secure and direct person to whomever you’re choosing to be in a relationship with, and communicating honestly about your needs openly.
Another important key to a successful relationship is not giving up. We live in a society of attention deficit disorder, instant satisfaction and divorce. When the going gets tough, people tend to get going. This is no way to treat another human being. When you are committed to someone and you truly love them, you need to stand by them no matter what. Money, communication, family, lifestyle choices—there are many challenges for new relationships, but you have to show your partner that you are there for them through it all. If they are ever standing there poor, beat up, out of shape and completely abandoned, when they turn around you need to be standing there ready to pick them up and love them. When you know that you are truly there for one another, your relationship will go to levels that you didn’t know were possible.
That ties into the last bit of advice we’re going to give. We have faced real life struggles together, and you will, too. Sometimes you’re poor, sometimes you’re rich, sometimes you may struggle with depression, addiction, aging, family trouble, careers—the fabulous possibilities of what’s coming your way are endless! Regardless of the challenges that life throws at you, if you can get through them together and walk down the path holding hands and supporting one another, your relationship will blossom. You never stop learning, and you never stop cultivating a deeper relationship with one another as life goes on. Take it from two people who literally couldn’t be any closer: There is nothing better than to always have a best friend, teammate and someone who will love you, is there to support you and someone you can have fun with in life.
6. A dating horror story from Heklina
Ah, Christ, is it that time again? Fucking Valentine’s Day rears its hideous head every year, its only purpose being to remind me that I suck at relationships. I’m actually staring at my cat as I write this. I’ll spend Valentines Day with him and a pint of ice cream. Good times! I guess the reality is I’m “married” to my work. It’s all I have time for.
But I’ve had my fair share of relationships. They just happened to be of the fucked-up kind. My worst Valentine’s Day ever? My first San Francisco boyfriend and I had a romantic date night that ended in a drunken fist-fight outside a karaoke bar. He followed me home to the Lower Haight, climbed my fire escape, broke my window, climbed into my apartment and we fought all night until we finally gave up, fucked and fell asleep. Hey, I didn’t say it was a funny story. It just sucked! Is it any wonder I’m settling for my cat and ice cream?
Catch Heklina every Saturday night at Mother, her party at San Francisco’s Oasis, and follow her on Instagram here.
7. A V-Day horror story from Kelly Mantle
A few Valentine’s Days ago, I performed at a show called “Love Is a Drag.” Afterwards my boyfriend took me out dancing. Feeling his oats, he started spinning on the dance floor. He lost his footing and fell head-first into the corner of a glass table. Naturally, it cut his forehead open. He was bleeding everywhere. Well, I just happened to have a maxi pad in my purse (because ya never know when things are gonna get real). So I slapped that maxi pad on his forehead to control the bleeding and drove him to Cedars Sinai. There we were, sitting in the ER, on Valentine’s Day, me in full dragoola, he with a maxi pad taped on his forehead … and in love with My Bloody Valentine!
8. A sexy dating tip from Monistat
Here’s a dating tip: After a nice shower, put some toothpaste around your anus for a tingly sensation that is sure to leave your lover with a minty fresh taste in his mouth during in flagrante delicto.
9. A breakup story (kinda) from Meatball
One year, to avoid going out on Valentine’s Day, a friend and I picked up a bunch of fried chicken and rode on the subway all the way home, just stinkin’ like KFC. We decided to swing by a liquor store on the walk home, where they made us leave our bags on the counter while we shopped. We bought our booze, but our chicken was gone. Someone had fully robbed us of the chicken and nothing else. So I guess that was my worst breakup — wait, what was I supposed to be talking about?
10. Sherry Vine’s top dating tip
My number one dating tip is always “get the money first!”
Follow Sherry Vine and her great video parodies on her YouTube channel.
11. A dating tip for drag queens from Amanda Poupon
One of the best parts of being a queen is spending time with the gay community of NYC on a regular basis. You get to laugh, play, drink, blackout, dance, “go to the bathroom,” blackout again and wake up just about anywhere with some of the most fun people in the city. You also get to be this wild and crazy cartoon version of yourself, and people are inevitably charmed by your very presence.
But what happens when the person enamored by your wit and sass is also a regulation hottie that makes your tuck unfurl?
My tip is to always bring a boy bag! If you’re hosting a drag brunch, and you get the side-eye from a potential boyfriend — or even bedfriend — it’s best to capitalize on the momentum, hunny! Kill your numbers, collect your coin and then get the fuck out of drag! Gag him with your handsome boyness while your gaff is still warm in your dragbag. And get practiced on a sensible boy beat.
Taking off the makeup can leave you looking a little raw … and not in the good way. Spook yourself, watch him go from impressed to intrigued, and don’t put out until you’ve washed your junk! (Unless you’re into that.)
Follow Amanda Poupon on Facebook.
12. A sad tale from Yolanda
It was Valentine’s Day, about four or five years ago, and I had no boyfriend. So I ended up selling Valentine’s Day balloons to people in love. That’s how fugly my life is.
13. A couple dating tips from Orchid
It’s Valentine’s Day, and a friend of mine — who has made it abundantly clear on multiple occasions that he wants more than a friendship — has asked if he can come over. I didn’t have anything better to do, so I obliged. After seeing his car pull up, I stepped out to the landing of my second-floor apartment to witness something truly horrifying: There he was, standing at the bottom of the stairs holding the least romantic thing you could possibly give someone.
“Are those red roses?!” I screamed. The question was rhetorical, of course. I could clearly see the tacky bouquet of cheap crimson flowers, rife with baby’s breath. “Those better not be for me! I swear to God if you bring those awful things up here they are going straight into the trash!”
He did. And they did.
Now, this story may sound harsh. It may depict me as a heartless, tactless, narcissistic cunt. And while all those things are true, it was a necessary lead-in for my first tip: Red roses are cliché. The most cliché. In my mind that means thoughtless, and thoughtless is never romantic. So if you’re trying to impress someone, never show up with red roses.
My other tip is a little more succinct: Olive oil is not lube.
Follow Orchid on Instagram.
14. A drag queen horror story from Daphne Sumtimez
I met some college boy off of Grindr, and it came up that I was a drag queen. Instantly, that was all he seemed to care about. So much so, in fact, that while I was servicing him orally, he said, “I hate to talk during, but how did you get your drag name?” I didn’t really know how to react, so I just kind of looked at him for a moment, then got back to work. A few seconds later, he asked, “So how many wigs do you have?” In disbelief, I finished the job and left. We never spoke again, but he still likes my posts on Instagram.
Follow Daphne Sumtimez on Instagram and Facebook.
What do you think of these dating tips and horror stories? Do you have any of your own?
This story was originally published on Feb 8th, 2017.
Read more stories by just signing up
or Download the App to read the latest stories