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Spilling MORE Tea, Part 3: Dating a Drag Queen was a Disaster

  • The Oolong Drunk
  • 54 minutes ago
  • 10 min read

Hello hello, dear reader! How has your week been? Did you drink a yummy tea this week?


By the way, I’ve been meaning to ask you, have you ever been to a drag show before? 


First things first: Drag is an art form, and many local drag artists perform for little-to-nothing. Now, not that I’m trying to get all preachy on you, but go support local drag! 

However, today, I’m going to tell you about how I tried to date two different drag queens, and how it was a disaster. 


(It killed me to not say ‘dating them was a drag’ by the way.)



Note: This story is NSFW, and intended for mature readers.



First, we need to travel back in time to last fall. 


Last fall, I was in-between jobs. When I left my place of work (which was the one mentioned in last week’s post), I was slated to start a new job. Due to the hurricane that hit Florida and the floods that hit the Smoky Mountain Range, my start date for the new place of work was delayed. In these 6 weeks of not working, I decided to go out in the city more often. Cause, why not? I’m single, can stay up late, and won't be able to do this forever. So I started going to different drag events downtown. 


This is where I met Lipstick Teeth. Lipstick Teeth is a drag queen in the city whom I met, and after some time, we built a very close friendship. One night, she invited me to a show she was hosting, and I came out to support her. Out of all of her friends, I was the only one to show up. In fact, the venue was relatively empty. Lipstick Teeth was cute, and despite that they were corny (and although their make-up was smeared) they sold the bit very well. I wouldn’t rank them high on the list of drag performers, but they tried. 


Eventually, Lipstick Teeth and I started chatting more and more. As our friendship developed, I noticed something: They posted a snapchat story that said, “There’s a boy I like, wish he’d finally ask me out.”

I stared hard at it, and in a sense, it almost felt like it was directed at me. Lipstick Teeth and I had been talking on a regular basis, and there were light flirtations in some of their texts. After taking a bit of time, I eventually asked Lipstick Teeth out. 


However, after texting back and forth for several weeks and trying to get our schedules lined-up, I eventually offered to drive into the city to meet them.

They replied, “I would love for you to drive down, but, you don’t live in the city. Sometimes I want to hang out and it’s hard with you being the next town over. I would hang out with you in an instant, but, you don’t live in downtown.”


I stared at my phone and felt disappointed. I had driven to the city many times to befriend and support Lipstick Teeth, and yet, I felt crushed because all of our connection was intently redacted to being conditional and convenient. I’m not gonna lie, dear reader, that this hit me particularly hard. I had been rejected by many city gays before for not living right in downtown. However, this person in particular grew to know me as a person, and yet, still reduced our connection to something as materialistic as me living 30 minutes outside of downtown.

I quickly removed Lipstick Teeth from my social media and parted ways.


Later that night, I was feeling distraught. So, I went to do the one thing that I enjoyed doing: Go watch drag.


You see, dear reader, I love going to drag for many reasons. However, the top reasons are, I get to be surrounded by other people on the queer-spectrum, which makes me feel like I belong. Another reason is the escape from it all. Every time I’ve watched a drag show, I’ve always felt more refreshed, confident, and loved than I did before. I could go further into why, but for the sake of moving today’s story along, I’ll continue…


That night, I ran into another drag-queen friend whom I already known named Samantha. Samantha was a house-queen at this particular gay bar I frequented, and she was more than phenomenal. Samantha was born to be a performer, and every time they performed, there was a stillness in the air. They were, and still are, incredibly special. 

Later that night, Samantha came out on the patio, and she and I chatted for a bit. We even went to the dance floor and danced with each other for a bit. Eventually, we exchanged numbers and parted ways for the night.


Later the next day, I was on a dating app (one of the serious ones, not the hook-up ones) and saw a guy named ‘Samuel’ on my screen. 

Although I had never seen this person before, I immediately knew it was Samantha, just not in drag. 

I had never seen Samantha’s boy self before, but I instantly knew it was them. 

My face lit up as I swiped right -- hoping that we’d match.


We didn’t. 


However, a week later, I went back up to the bar and went to a drag-show led by Samantha. Just like always, Samantha was incredible. She didn’t only steal the show, she was the show. Samantha was cute, bubbly, and worked the audience with such ease. Seeing Samantha was the highlight of the night.

After the show ended, Samantha and I hung out again. We danced, hung out on the patio, and shared a drink. Then, after I left, I opened my phone to a text from Samantha.


“Look, I don’t know if you’d feel the same, and I hope it’s not awkward to say so, but I really like you and I’ve liked you all year. I really think we could be good together, and we could make an incredible couple. I know I perform a lot, but I know you can handle it, but I really like you and hope you feel the same.” 


My heart melted. 


With the largest smile on my face, I replied and said, “Yes! I’ve liked you for a long time as well. Before we make anything official, let’s go out and spend time together. I want to meet Samuel. I know Samantha, but I want to see Samuel too.”


They replied, “Yes! Let’s go out. I’ll be busy this next weekend, with work stuff but lets grab dinner sometime after.”


We agreed on a date, and everything was set in motion.


That next weekend, I went out again. Samantha was performing, and we wanted to see each other. I walked into the performance room, and Samantha ran up and hugged me. She called me cutie, and I called her cutie was well. Despite that she was busy, she looked like she wanted to spend more time with me, but, had to leave and start the show. 

Halfway through the show, in between sets, Samantha asked the audience if she could have 4 volunteers from the audience to play a game while waiting for the 2nd set. I immediately stood up and volunteered. While standing on stage alongside 3 other volunteers, Samantha brought out a large box and handed all of us a wig, and announced to the crowd that we’d be taking turns performing drag, and whichever person got the most cheers from the audience, would win a prize.


I blushed, and had no idea that I had volunteered to do drag, and on the spot. However, its as okay, because Samantha was there. I felt safe around her. I knew that I’d be okay.


Samantha pulled me back stage, and as the DJ was getting my track ready, Samatha guided me to the middle of the stage curtain. She fixed my wig, and then spoke into her microphone and announced, “Next we have Cody, whose going to perform Green Light by Lorde!”


The crowd cheered, and as they did, Samantha stopped. 


She slowly leaned up, guided my chin up, and softly kissed me on the lips. 


In that moment, all time had stopped. The music, the stage lights, and the audience’s cheering came to a deafening halt. It was her lips on mine. 

That was the exact moment I knew definitively that I wanted to be with her, too.

She stepped away and pulled the curtain back. As she did, I continued on to perform Lorde….


Side-note: I know my peformance was something lol. But hey I got $4 in tips at least. 


The next week, I got a text from Samuel an hour before our date. 


“Hey, I’m SO so sorry, but can we reschedule dinner? Work called me to come in last minute. Can we do Friday?”


I replied and said, “Sure, let’s do Friday then!”


On Friday, around the time I was leaving to drive down to see Samuel, he texted, “Hey, I have to go into work again and I can’t tell them no. Can we aim for Sunday?”


Then on Sunday, they texted, “Hey they double-booked me last minute as a fill-in, can we do next weekend?”


And that next weekend, they texted and said, “I have to cancel, but I know for sure I’ll be free on Tuesday.”


Then, I got upset. At this point, I had been canceled on the time-of, 4 times in a row and had been talking to Samuel romantically for over three weeks and still couldn’t go on a single date. I was getting tired and that spark was practically gone.


I replied, “Hey, this isn’t working for me. If you’re too busy, I understand. But, I don’t think it’s fair to tell me you want me and need me, and cancel on me the time-of our date.”


Samuel replied, “I know, and I’m sorry, I’m just busy and I can’t help it. Being a performer is a lot.”


To which I replied, “Yeah, but so many of the drag performers at your work get booked as much as you do. However, they’re all in relationships, and they’re always doing things with their partner. If you really wanted it to work, you’d make time. However, I want you too, but it’s not fair to endlessly dangle a carrot in front of my face and nothing ever happens. I have feelings, too.”


Then, Samuel texted and replied, “…I’m sorry.”


And that was the last time we texted.


Later that night, I went back to the club to dance. Samuel was working at a different event that night, so I didn’t have to worry about seeing him. However, this time, I avoided watching drag and dance on the dance floor all night. I wanted a distraction from my distraction. I was still heart-broken from Samuel, and you know what they say; the best way to get over someone is to be under someone else (or in this case, on top of someone else).

However, as the night progressed (and after a shot), I was curiously growing Grindr when I got a message from a tall wwink. They had a shirtless-torso photo, and after chatting for a bit, we agreed to meet up. 


I got in my car and as I began to leave, I asked them for a face photo. Then, right after, they sent me a selfie. 


It was Lipstick Teeth. 


"Fuck the community is small", I thought to myself.


I held my breath as I sent them a face photo of myself, hesitant about how they’d reply.


“Oh hey, nice to see you again,” they said. 


I replied, “Yeah. Given our history, I don’t know meeting is a good idea or not. I just broke it off with Samantha. I also wanted to date you as well, but look how well that went. I don’t want this to further affect our connection.”


Lipstick Teeth replied, “Well, I don’t mind. You can still come over, and we can still fool around. It won't mess anything up.”


I hesitantly replied, “Yeah, but I wanted to be with you in a romantic way. I don’t want a hookup from you. I really wanted to date you.”


Liptstick teeth replied, “I don’t know, I thought I wanted you too, but I don’t know what I want right now. I mean, I still want you.”


I then questioned further, “So if you want me, then be real with me. Do you actually want me or not? Because you keep telling me you want me, but you can’t meet me halfway to make it work. So which is it?”


There was a pause between replies, and after a moment, Lipstick Teeth replied, “I do want you but I don’t think we should date. You live too far… But you can still swing by and we can still fuck bare if you want. It would be hot if you left your load in me.”


I looked at my phone, and without hesitation, I blocked their profile….


It’s safe to say I didn’t go back to the club for at least several months.


So what did I learn from that this? Is dating Drag Queens really a drag? 


(I know I said I wouldn’t say it, but I lied.)


First things first, I learned to never date an employee of any establishment that I frequent ever again, especially if it’s a gay space. For myself, there are not many safe spaces and gay spaces for gay people to exist freely. Given that the spaces we have are limited, I don’t want to have to further dilute the few options for safe spaces I already have.


For as large as the gay community is, it’s still too damn small.


Second, I don’t think I’ll ever date a performer again. Now, this isn’t to say that my experience with Samantha or Lipstick Teeth would ever be repeated again. However, I don’t want to put myself in a situation where my connection to someone is conditional on their inability to have a healthy work-life balance. Or, put myself in a situation where my connection to someone is conditional on something like living 15 minutes outside of a city-gay's driving radius. 


In the end, we can only be so flexible and forgiving before we need to start being forgiving to ourselves. 


You need to be fleible for yourself. The way that I'm flexible, is know that I'll drive any distance for myself.


How about you, dear reader? Are you remembering to forgive yourself? Will you go the distance for you?


After all, you’ve always been here for me, and never made my distance conditional <3


Try and take care of yourself this week, dear reader. 


Until next week,


~Cody Wade

Aka The Oolong Drunk

“Blissfully Tea Drunk”

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