“That is so 2024,” my friend gasps over FaceTime.
“I know, right?!” I squeal as I squeeze my phone even tighter, my face illuminated by my iPhone screen. It’s 9 p.m. on a Tuesday night and I’m telling her about this city boy I’m going to meet up with over the weekend.
*PAUSE* Let’s rewind. I am in a Discord group chat for a bunch of chronically online individuals, mainly hot married men and a sprinkle of hot women (like moi…this is self-love, btw), who all listen to the same internet personalities. I’m trying to keep this vague to not dox myself or anyone, so please forgive me if I don’t mention who these internet personalities are. You’re not missing out, tbh.
In this group chat we shoot the shit, i.e. we talk about our favorite internet people’s hot takes, what everyone is cooking or wearing. Chill stuff. One dude in the chat, let’s name him Oleg, is a city boy. Literally. He’s from San Francisco. He seemed fairly normal in the chat. I gauged he was in his mid-20s from his view of work. Like a classic member of Gen-Z he once complained about a workplace memo regarding his manager’s expectations in arriving and leaving work at a certain time. “Yep, sounds like he’s part of my generation,” I thought to myself.
As a Sactown gal, I’m perpetually in my Lady Bird era. Always dreaming, looking ahead, wanting something more. It’s my year of putting myself out there. Whether it’s to make new friends, sharpen my social skills, or “do it for the plot,” I had this “YOLO” mentality in the back of my mind as I messaged Oleg. I was heading to the city for a comedy show, so perhaps we could link up for a little beverage. I’ve also been thinking of moving to San Francisco, so why not get the tea from a well-seasoned city boy?
*WE’RE BACK* I’m telling my friend about all of this and I would be lying if I said I wasn’t a bit nervous. As an anxious person who overthinks, I was spiraling. “What are we going to talk about? Will it be fun? Why am I doing this?” I would also be lying if I wasn’t a tad bit intrigued by this guy. I mean, a cool urbanite who lives a couple of hours away from me who has similar interests? SIGN ME UP. WE DON’T GET A LOT OF THOSE IN MY NECK OF THE WOODS.
*FAST FORWARD* Oleg and I meet up at this delightful North Beach bar.

selfie at City Lights before meeting up with Oleg. outfit details: Uniqlo x +J puffer (no longer available), J.Crew earrings (similar)
Spoiler alert: it wasn’t awkward at all. We chatted over Negronis and the energy was vibrant. Maybe it was the inviting space, people’s nearby conversations booming loudly, or just the idea that this bar was once filled with artistic deep thinkers, that I was on cloud nine. I could tell this guy knew how to work it. He tapped my knee when telling anecdotes about his homies, or his depressed roommate who apparently used to be a thriving social butterfly in college who could get any girl he wanted.
“Now he’s a sad sales dude in tech,” Oleg exasperatedly said while taking a sip of his drink.
“No, I don’t think he’s sad. He just peaked in college,” I shot back, to which he leaned backwards laughing, not noticing how he almost knocked over a drink behind him.
He was charming, witty, and funny. At one point some bloke walked in and high-fived Oleg. “Oh, wow. You’re popular here!” I told him.
“I just paid him $20 to do that so you’d think I was cool,” he responded. He was quick on his feet and I left our hangout as a smitten kitten. I showed up half an hour late to a dinner with my sister and brother-in-law because I got held back at the bar with Oleg’s cheekiness. My smile was wide for miles and couldn’t be wiped away, even if anyone tried!
It felt nice to meet someone who was interesting to talk to and seemingly had good chemistry with me. However, as a hopeless romantic, I knew this was just a fantasy. Yeah, I was attracted to him, but let’s be real. I didn’t know anything about him, so I pushed those delusions away.
However, it didn’t help that we continued to banter over text. Oleg just had this charm and I couldn’t help but swoon when he used my name in conversation. Who knew that would feel so good?! But, oh how the tables turned. We were texting about the upcoming Super Bowl and shortly after our exchange, Oleg sent a life update to our Discord chat: “…first time going out for real tonite since my break up. Not looking for anything besides falling back in love with myself…”
I see this message and my jaw drops. Clearly this message is for me. It’s an indirect way of letting me know that our cute little banter is literally just that, which quite frankly makes me upset at the moment. But then it’s also a blessing because this guy decides to be upfront, even if it’s just via a mutual group chat (so Gen-Z). Honestly, I should’ve just stopped texting him then and there. Funny enough, I wasn’t being overly flirty…He on the other hand was dropping things like “Ms. Tori,” or “game day fit check?” Like, how am I not supposed to be in dreamland after cute texts like that?
I entertained the conversation for a couple of days after that. Yeah, I sent him a cheeky fit check. But, I also didn’t drop everything when he flirtatiously said, “maybe you should come with me” when I suggested he should find the best Espresso Martini in the city. Like, no. You need to fall back in love with yourself and I am not running after you, city boy! It was then and there I realized this guy doesn’t want anything deeper with me — only a little fun.

the game day fit pic I sent to Oleg 🙃 btw, I wouldn’t recommend doing this. outfit details: Adidas Originals x Wales Bonner t-shirt, Stüssy pants, Anne Klein purse
Long story short, I just left him on delivered. When someone tells you exactly where they stand and how they’re feeling, believe them. This city boy did nothing wrong and I’m not mad at him. In fact, he did an anxiously attached girlie a huge favor. He said where he stood and flirted his way through to get whatever he needed to get. Be it validation for his post-breakup self, an ego boost for his unemployed self (he got laid off), or just some good old-fashioned attention.
As for me, he showed me to take things for face-value…to believe people when they say who they are, to observe people’s words and actions, and of course, the most tried and true lesson: if they wanted to, they would. In the end, I truly didn’t like him either. What really happened was that I got swept up in the idea that he liked me just enough to keep me constantly guessing where that “just enough” line was. Could this be more? How much more? What could I do to make that line disappear?
Hate to break it to myself (and you, dear readers), it’s not worth doing anything for someone who doesn’t feel the exact same way about you. Why go through the big emotions, all the highs and lows of flirty banter that leads to nowhere, and the constant guessing if this could be something more? All I know is that there is someone out there for me who won’t keep me guessing, someone who won’t tell me their feelings indirectly, but instead, will make it clear as day that they like me and they want me as I am. They’re out there and in the meantime, I’m going to do what Oleg’s doing now…I’m going to love myself, too, city boy!
Image by Scigola via Pixabay
