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A Lady Flirting at Trivia Evening
New-York News

A Lady Flirting at Trivia Evening

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Last updated: May 17, 2025 5:14 am
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Picture-Illustration: Marylu Herrera

On this week’s story, a lady who’s touring for work finds the correct place to fulfill queer ladies: 34, single, New York.  

DAY ONE

8:10 a.m. I drag my ass off the bed. It is not sensible that I’m this exhausted given I went to mattress so early final night time. Psychological word to get my blood work checked — am I dying? Why am I at all times so torpid? I’m solely 34!

10:45 a.m. My first job of the day begins now. I’m a private assistant. My boss is a TV character. He’s homosexual and really good. Day by day is a brand new journey. Proper now, I’m tasked with choosing up a catering supply and bringing it to his condo to assist arrange a lunch assembly he has there.

1 p.m. My boss invited me to hitch the lunch assembly. It’s with a producer who he typically collaborates with, however they wished to have the assembly within the privateness of my boss’s condo since they’re discussing one other actuality star who’s been within the information not too long ago and so they need to be discreet. He at all times consists of me in these conversations. I’ve been with him for nearly ten years — typically we really feel extra like enterprise companions than the rest. We’re each single and queer, so we discuss our love lives on a regular basis too.

4 p.m. I’ve to return three enormous duffel baggage of garments to the RealReal. I don’t know if my boss wore any of them, or why he had all these outfits. I simply should get it finished. Standing in line there, I remind myself to ask for a increase. My fucking again is breaking!

6:30 p.m. Drinks with my buddies. Most of us know one another from the theater world. We’re all striving actors, together with myself, though it’s been at the very least a 12 months since I auditioned for something.

9 p.m. I seize two slices of pizza and head house. I’m on a break from the courting apps, so my nights are quieter than ever. I used to scroll for hours upon hours. I’m making an attempt to regulate to the nothingness of life with out the apps, however the break is nice — I actually assume I used to be hooked on them.

10 p.m. I’m too lazy to go get my vibrator, so I masturbate the straightforward method, with two fingers and my creativeness. I take into consideration the salesgirl on the RealReal immediately. She was fairly, type of goth, type of bitchy. I ought to have requested her out, however truthfully, I simply wished to get the fuck out of there.

DAY TWO

7 a.m. My boss meets along with his coach on Tuesday, so I often stick round and assist undergo his emails and scheduling and different unfastened ends whereas he works out. So immediately, I’m sitting within the nook of the health club (in my boss’s condo constructing), going by means of all the pieces, interrupting his session with this and that. It’s a great way for everybody to multitask.

10:45 a.m. We’re at my boss’s kitchen desk going by means of his manufacturing schedule for the upcoming 12 months. He seems at his cellphone and tells me he simply acquired a textual content from a man he’s been seeing. I do know that this new man is a grimy canine. A number of years in the past, he began courting certainly one of my school buddies, and he was not very good to him; he would disappear for weeks at a time, that type of factor. I’ve warned my boss however attempt to not get too concerned. We have already got some points with boundaries (in that we don’t actually have any), and I don’t need to overstep.

2 p.m. We have now a working lunch collectively in Soho. The waitress is scorching, and my boss awkwardly asks her if she’d go on a date with me. She says she’s straight and has a boyfriend. Awkward!

5 p.m. I textual content Gia, a woman I’ve been casually seeing. We met by means of work, at an occasion my boss introduced me to. I’ve a enjoyable work occasion tomorrow and wish a date. She’s however has to maneuver a number of issues round. She’s a stylist and is at all times touring and dealing, however that’s not the actual challenge for us. The actual challenge is that Gia isn’t out to her very large, very Italian household. At first, there was one thing attractive about that. But it surely turned type of icky after I innocently posted the 2 of us at a charity occasion and he or she requested me to take the publish down. That simply felt bizarre. She’s from a spiritual household, so I respect it, but it surely simply feels incorrect to be with somebody who nonetheless has a conflicted relationship with homosexual individuals. Regardless, she’s beautiful, and the 3 times we’ve had intercourse had been insane, so I’d like to see her tomorrow.

8 p.m. My boss and I are at a documentary-film screening. It’s onerous not to go to sleep. Once more, I’m at all times torpid!

10 p.m. My boss is hamming it up on the after-party and I’m in an Uber house to mattress.

DAY THREE

9 a.m. Get up exhausted. WTF. This time I actually do schedule some blood work. They are saying I can are available tomorrow morning, however I’ve to quick the night time earlier than, and I plan on having enjoyable tonight — so no thanks. I make an appointment for subsequent week.

11:30 a.m. I spent a number of hours enhancing my boss’s subsequent e-book. I’m proofreading, giving notes, giving suggestions. He’s a good author, so it’s not a tough raise.

2 p.m. Gia says she will be able to make the occasion tonight. It’s a fundraiser for a charity that my boss is concerned with. Her textual content jogs my memory that I’ve to select up my gown from the dry cleaner. I used to be speculated to get it weeks in the past; I hope they didn’t eliminate it. Excited about the gown jogs my memory of the primary night time I wore it. I went to a good friend’s birthday celebration and ended up leaving with this drunk couple from Connecticut who had been randomly on the restaurant. They had been, like, very fancy individuals who had been secretly swingers. They came visiting to me and requested if I wished to come back house with them. I didn’t need to Uber to fucking Connecticut, however I used to be positively drunk and feeling adventurous, so the husband acquired us a room at a resort. I ended up taking place on his spouse whereas he watched. I’ve had threesomes earlier than, however this one was proper out of a nasty porno. It truthfully gave me the ick the second I sobered up, but it surely made for an excellent solely–in–New York story.

6:30 p.m. Gia meets me within the entrance of the venue. She seems unbelievable; at all times the best-dressed lady within the room. I kiss her on the cheek howdy. Gia likes me, however the final time we frolicked, I advised her I wasn’t comfy with conserving our fling a secret. She understood what I used to be saying. I’d like to not discuss any of it tonight and simply have an excellent time. We begin with drinks on the open bar.

9 p.m. The occasion had numerous speeches, and it was a serious turn-on having Gia contact my thigh whereas the individuals spoke. My boss was at one other desk, so I may actually loosen up and simply benefit from the night time together with her.

10 p.m. We’re again at my condo, hooking up. I’m so interested in her. I like her physique and the way in which she smells. It’s like cotton sweet, however not in the way in which that provides you a headache. She sleeps over and we maintain one another for many of the night time.

DAY FOUR

8 a.m. I go away Gia sleeping in my mattress to run to a photograph shoot for my boss. I want to select up espresso and bagels alongside the way in which. He additionally texts me to get some “headache drugs,” which suggests he most likely scored as large as I did final night time.

10 a.m. The shoot is at a studio in Brooklyn. It’s cool. The stylist on set is aware of Gia, so we take a selfie and I ship it to the sleeping magnificence. I inform the stylist that Gia is at the moment in my mattress, and we’ve got somewhat naughty chortle. The minute I say it, I ponder if I’ve violated some privateness factor. It’s so bizarre and unsettling being with somebody who hides their private life the way in which she does.

12 p.m. Fortunately, Gia hearts the selfie and it doesn’t flip right into a factor.

2 p.m. It’s an extended day. Shock, shock, I’m drained. I order iced lattes for everybody on the shoot. I like spending my boss’s cash. He’s extraordinarily beneficiant, so it’s effective. As soon as once more, nevertheless, I remind myself it’s time to ask for a increase.

6 p.m. Everybody from the shoot goes out for a bottle of Champagne. Somebody asks if I plan to be a private assistant eternally. It’s onerous for me to reply that. I actually love my job, however I notice it’s not essentially the most formidable profession. I at all times wished to behave, but it surely’s unattainable to get good roles. And I’m getting older. The reality is, I’m nonetheless undecided what to do with my life. I reply the query by saying I like what I do, and I’m compensated properly (reality, kinda), and that’s all I do know for now.

10 p.m. I’m texting with Gia concerning the enjoyable we had final night time. She’s house in her personal mattress now. We’re flirting and sending selfies and laughing. I’m afraid to ask her if she’s had extra talks together with her household about her sexuality. I’m too drained to actually broach the topic proper now anyway. Or perhaps I don’t need to know the reply as a result of it can destroy my afterglow from final night time.

DAY FIVE 

9 a.m. In an Uber to La Guardia. My boss has an occasion in L.A., and I’m going with him. I like going there. It’s at all times very fabulous, and the queer ladies in L.A. are plentiful and attractive as fuck.

1 p.m. On the airplane, I attempt to learn the brand new Tinx novel, however I can’t maintain my eyes open. Movement at all times places me proper to sleep.

3 p.m. We’re checking into the resort. I see a random TV star who my mom at all times crushed on after I was youthful. I textual content my mother that I’m standing subsequent to him at reception. She FaceTimes me instantly. If my boss weren’t there, I’d ask the actor to say howdy to my mother, however that’s too inappropriate proper now, even for me.

6 p.m. I’m alone tonight. With out the courting apps — which I’m nonetheless abstaining from — it’s onerous to determine find out how to meet somebody. I resolve to go to a bar I like in Silver Lake and simply see what occurs.

7 p.m. Sitting on the bar and it’s all straight individuals, plus nobody is speaking to me.

9 p.m. Again at my resort room with room service.

DAY SIX

8 a.m. Large breakfast assembly in my boss’s resort suite. His complete L.A. workforce is right here. It’s a pleasant crew. They’re all actually good to me. Then once more, I’m the one who takes everybody’s breakfast orders, manages the scheduling, and makes certain all the pieces is about up.

1:45 p.m. We transfer to a different resort, the place there’s one other assembly with some studio executives. There’s a brand new government, Kate, who seems queer and is speaking to me greater than she must. I ask her the place I ought to go tonight, and he or she invitations me to a trivia night time she’s attending. So L.A.! It seems like I’ve hit the lottery with this invite, nevertheless, so I get all the data and really feel excited.

4 p.m. Fast nap in my resort room.

5 p.m. My boss texts that he kinda needs to come back to the trivia night time, however I politely inform him that it’s women solely. I’m undecided of this truth, however I actually don’t need him to come back, and I believe he understands what I’m saying.

6 p.m. One other lengthy and costly Uber to Silver Lake (on my boss’s dime, however nonetheless). After I stroll into the bar, I do know it’s an excellent crowd for me. Queer L.A. hipsters. I adore it. Kate comes over to me and introduces me to her buddies. There’s a strikingly lovely lady named Ivy who catches my eye instantly. She’s an actress and crushing it. She’s humorous, good, and grounded. She’s so scorching.

9 p.m. Ivy’s girlfriend will get to the bar simply as we’re all getting tipsy and beginning to discuss our love lives. Damnit. I’m a lot cuter than her too! I go searching to see who else I’d be into. I don’t need to go there with Kate, as a result of it feels somewhat too shut for consolation.

10:30 p.m. I am going again to the resort and not using a hookup and really feel somewhat lonely. However I met some good individuals to reconnect with the subsequent time I’m on the town, and I’m right here on a regular basis, in order that’s going to repay.

DAY SEVEN

10 a.m. I’m not a giant Instagram particular person, however I see that Ivy despatched me a DM. She wished to let me know that she’s in an ENM relationship, and that she thought I used to be actually fairly. Instantly, I’m like, in love together with her.

11 a.m. Within the automotive to the airport, I take a look at her photographs and I like what I see. Shit, when can I see her once more? We go away tonight! I inform my boss concerning the scenario. He generously gives to pay for a change in flight, however we’re already on the way in which to LAX, in order that feels excessive. I admire the gesture, although.

1 p.m. Simply earlier than takeoff, I DM her again that I used to be so into her final night time, and I want I knew I used to be allowed to flirt together with her. We transition to texting. However the airplane is taking off quickly.

6 p.m. Again house in my condo, the texting with Ivy continues. She’s witty and provocative. She’s coming to New York subsequent week for an in-person audition. I jokingly inform her that she will be able to keep at my condo. She’s like, “Perhaps?” Wow. That is on. 

9 p.m. Gia texts about hanging out this week. I virtually forgot about her. We make plans for later within the week, however after a lot dialog with a proudly queer lady like Ivy, I’m not that into Gia.

11 p.m. I go to sleep after jerking off to ideas of fucking Ivy. I’m going to inform her that within the morning, too.

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