a gen z guide to enjoying dating

7 tips for flirting, having fun, and not wanting to die while dating

Feb 02, 2025

y’all loved the first edition, a gen z guide to touching grass, so i’ve dug into my arsenal for more life hacks you can actually use! last time we attempted to cure gen z’s social anxiety, and now, we’ll be facing a far more daunting terrain: whatever the hell is going on with straight dating.

i’ve long felt impassioned about this subject, because if there’s one thing i’ve learned from a decade of content consumption, fifteen seasons of love island, and hundreds of tear-laden conversations with my friends, it’s that twenty something year old girls are not enjoying dating.

as if love wasn’t already complicated enough, gen z is now forced to contend with a host of unforeseen adversaries, including but not limited to: dating apps, situationship culture, phone-based relationships, and a media landscape that’s poised men and women as mortal enemies.

you can find a million and one pieces of content that lament the state of modern dating and wallow in the seemingly impenetrable nature of these obstacles, but that is not what we’ll be doing here. what we’ll do instead is figure out how to have a good time in spite of these less-than-ideal circumstances, because we are not quitters!

despite what the headlines may report, i’m confident that it’s still very much possible to enjoy dating in “this day and age.” in fact, i had lots of fun going on dates when i was single. (unless you’re my boyfriend reading this, then it was fine or whatever…)

given my rare, positive experience, i feel it’s now my civic duty to put the girls of substack on-game. you may not find the most tactical insights here if you’re trying to secure a husband in the next 3-5 business days, but if you’re a single girl in your twenties who wants to:

ease some anxiety
stop stressing and start having fun

then you’ll likely find something useful below.

sooo, without further ado:

tip #1: don’t go grocery shopping while you’re hungry

🚨 warning: obligatory self-help tirade incoming. we’ll get into the good stuff after.

a wise woman once said never to go grocery shopping while you’re hungry, or you’ll end up with a cart full of junk food. or maybe i made that up? who’s to say. regardless, the principle still stands: don’t date while you’re desperate for someone else to fulfill you, or you’ll end up with nothing but high cortisol.

maybe i was born at the right time, evading the generational brainwashing that millennial women endured, or perhaps i’m just a natural-born hater, but growing up, i never quite understood why some girls would fantasize about finding their future husband — as if this mythical man would appear and make their lives finally make sense.

i quietly wondered, “do they realize they can get married and it can suck?” “what if this husband guy goes away, or he never comes at all? will they just lose it?” “aren’t there more fun things to daydream about, like eating snow cones with your friends?”

if you think i’m exaggerating, please read this poem i wrote when i was 8 years old.

turns out little steph was onto something, because this mindset has been the ultimate hack for enjoying dating as an adult. now that i’m slightly more eloquent, i can express it like this: searching for your “other half” or your “missing puzzle piece” is so poetic in theory. but in practice? it’s kinda tragic.

fixating on outcomes and made-up markers of security will only rob you of your capacity to enjoy the thrilling uncertainty of a fresh connection — and more critically, to feel complete as you already are. dating gets more fun (and, ironically, you get more favorable outcomes) when you start to relinquish some of this craving for control.

for all the lovergirls out there who got angsty reading that message: no, you shouldn’t abandon the quest to find your soulmate. that said, it’s still an incredible long-term investment to build a life that is full to the brim — regardless of your relationship status.

because, reality is, even if you lock down that fairytale relationship you always dreamed of, you still need to be cool and confident within it. otherwise, you’re gonna have a reaaal bumpy ride. you’ll only be able to unclench your jaw and truly enjoy your relationships when they’re born from a place of wanting — not needing — so try going all-in on your own life first. then, the real fun will start. 💅

tip #2: keep your tummy full

so, if the goal is to avoid grocery shopping while you’re hungry, then naturally, you need to stay well fed. this can be achieved by filling up your life with things that nourish you — like intimate friendships, fun hobbies, and a great sense of self.

let’s work backwards though, and assume you’re already submerged in the trenches, sick to your stomach because derrick from hinge hasn’t texted you back in 6 hours.

take a quick break from stress-biting your nails and try asking yourself this: if derrick didn’t exist, what would i like to be doing right now? better yet, what would i like to be doing if men didn’t exist at all?

if the answer is that you’d still prefer to be tweaking under your duvet, then there’s some added work to do here. but if the answer is that you’d like to try a new dance class, or facetime a friend you haven’t seen in weeks, or sip wine out of a fancy chalice while you paint sunsets in the park, then get up and do it right now!

it seems that in many instances, you don’t even like derrick that much. but for one reason or another, you’ve decided that his attention and validation are now the fuel you require to feel energized throughout the day. the reason is likely that your tummy isn’t full.

so, try filling your life to the tippity-top with people and plans and ideas that excite you. you’ll likely find that once you’re keeping yourself satiated on your own accord, derrick’s attention will no longer be a necessity — it’ll just be a sweet little treat.

tip #3: firstdatemaxxx

as i argued in tip #3 of my guide to touching grass, i’m a proponent of the idea that your plans should usually be nonrefundable. in this context, it means that if one morning you wake up and decide that it’s finally time to put yourself out there and set up a date, you should do it. and if date night rolls around and you really really really don’t want to go, you should still do it.

if you’re meeting people online, first dates can feel like homework. you don’t even know this person and suddenly you’re forced to feign excitement about eating tapas with them? it’s a bizarre ordeal.

still, picture this scenario: you get dolled up, trek all the way to this date, aaaaand… it absolutely sucks. you dip out hurriedly to get on the train home, where you sit with your fists clenched, bemoaning the fact that you wasted eyeliner on this night. suddenly, the cute guy across from you looks up from his book and asks why you look so pissed off. you two end up giggling the whole commute home, he takes you on the best date of your life, and then you two live happily ever after. the end.

whoops, i always skip to dramatics — i suppose an alternate scenario is that you end up hitting it off with the first dude. point is, no one meets interesting people or builds good lore when they don’t leave their house. no one makes movies or writes songs about people who don’t leave their house. no one really learns anything about themselves or the world when they don’t leave their house.

from this point forward, no more complaining about “the state of modern dating” if your screen time exceeds 7 hours a day. just go on bad dates, go on good dates — go outside and experience the world as it was intended. ok? ok.

and if you hate this tip because you hate first dates, please see tip #4.

tip #4: men love [silly] bitches

if you think first dates feel like glorified interviews, i am here to assure you that there’s no first date rulebook — you can make the conversation as deep or nonsensical as your heart desires. if you don’t care how many siblings he has or what he thinks of working from home, then literally don’t ask.

the cool part about a first date is that they typically don’t know much about you, so this can be an opportunity to reinvent yourself. you can play a character… subvert expectations… get silly with it... if you’ve always wished that you could be completely bold and socially confident, just try it on for the night. the best part is, if you like how it feels, you can keep it!

if you don’t know where to start, try writing a list of 10 fun questions in your notes app — these will be your armor to protect against small talk and awkward silences from now on. if you want to really amp up the theatrics, steal this script:

say, “can i ask you something kind of serious?” take a dramatic beat — perhaps clear your throat obnoxiously — then whip out one of your prepared questions. for instance, “who do you think was the hottest war general to ever do it?” then sit back and offer an inquisitive stare until you receive your answer. (bonus points if you ask that one and he’s not vaguely homophobic in response).

you’ll find your own brand of silly along the way, but here’s my case for committing to the bit at all costs:

it will lower the stakes of meeting new people
it will make you more socially confident
it will lead people to find you bizarre and hot in equal parts, which is arguably the finest concoction to be

tip #5: get your mind out of the gutter!

social media is uniquely adept at pitting people against each other, and in recent years, straight men have been public enemy #1. this is in part for good reason, but to all the women out there who still want to date men and enjoy it, you gotta stop ragging on them.

when you repeat ad nauseam that “all men are trash,” the trash will almost surely continue to find you. this is not only because your perception cements your reality, but also, because science says so. i recently wrote about this thing called reciprocity mindset, which argues that people tend to live up — or down — to the expectations you set for them. this phenomenon is especially relevant in romantic relationships, where your standards define your experiences.

so, if you want to attract good people and have a fun little time, try being purely and utterly optimistic about your dating life for just one week.

swap:

“i don’t trust men” with “i trust everyone until they give me a reason not to.”
“there are no good prospects out there” with “the world is literally brimming with cool people and i want to meet them all.”
“dating apps ruined dating” with “dating apps are a convenient tool, but there’s still a whole physical world out there for me to enjoy.”
“i don’t have another failed talking stage left in me” with “fuck itttt, we ball.”

say this stuff to your friends, say it to the people you date, say it to yourself in the shower — just say it all out loud, even if you think every bit is dangerously naive. you might just notice an unsuspecting pep in your step, and people might even start meeting your newfound expectations.

tip #6: don’t prove the podcast bros right

in the same vein, it’s probably smart to refrain from advertising your taste for losers, narcissists, and guys who don’t care if you live or die. you would think this much was obvious, but obviously, it’s not. spend five minutes on tiktok and you’ll find some variation of the below sentiment with thousands of replies to the effect of, “yas queen slay queen so real.”

call me a party pooper or a pick-me, but to all the girls reading, please know that these jokes(?) are way more damaging than you’d think. not only will this mindset award you a lifetime of subpar or even harmful relationships, it also incentivizes men to be annoying and poorly-behaved.

if you’d like to date decent humans, try doing the literal opposite of this. inform everyone around you that you only date people who treat you exceptionally well. it will motivate them to follow suit.

and if all this isn’t good enough reason to go cold turkey on the “i <3 red flags” rhetoric, just remember that andrew tate has made millions from preaching that women are turned off by respect. each self-deprecating comment you make is an extra dollar in that little freak’s pocket.

tip #7: don’t be a passenger princess

love ‘em or hate ‘em, one thing men have gotten right about dating is putting themselves and their needs first. they’ll watch the game when they feel like it, stay at the bar with friends ‘til closing, and generally just move how they want — regardless of their feelings for anyone else. women, on the other hand, tend to prioritize the wants and needs of whoever currently has their affection. us sweet little souls...

we consider this approach the more moral one, and deem anything else plain selfish. but the unfortunate reality is that there’s no prize for being “correct” here — all you get is a victim complex and battered confidence.

committed relationships require a different degree of consideration, obviously, but if you find yourself bailing on friends when your situationship commands you to “come thru,” then it’s time for a reframe. expeditiously.

it all circles back to principle #1: don’t go grocery shopping while you’re hungry. when you cling onto romantic connections from a place of lacking, desperately chasing those fleeting feelings of security and control, you tend to be shitty to yourself and the people who already love you.

most girls reading this can probably relate to the experience of being in a toxic or codependent relationship, feeling like you’re doing donuts down the freeway while someone else has control of the wheel. suddenly your mood for the day or your plans for that night are entirely at the whim of someone else’s decisions. you’re constantly ungrounded, waiting for their approval to bring you back down to earth.

if that’s how you’ve felt or currently feel in your relationships, i have good news: it doesn’t have to be this way! it’s up to you if you want to hop in the driver’s seat and start taking accountability for yourself. all it takes is a little reframe.

instead of this: ugh billybob won’t let me know if he wants to hang out tuesday or thursday… how am i supposed to plan my week now?? i just have to sit around waiting on his response?? fml fml fml ;((

try this: billybob has his own life and priorities, but so do i. i’ll plan my week how i want, and if he decides to put effort into seeing me, i’ll assess then.

instead of this: why hasn’t billybob asked me to be his girlfriend yet?? is it because i’m an unlovable swine?? or because he’s a gaslighting manipulator?? could it be both?? *cry, doomscroll, panic, hit vape.*

try this: billybob hasn’t asked to be his girlfriend yet. let me think about how i feel, or maybe i’ll have a chat with him. then i will decide how i want to move forward.

it can actually be that easy to take all the agency you’ve given to billybob and reclaim it for yourself. of course, our pesky little emotions tend to get in the way of sheer rationality, but with a little bit of confidence and a lotta bit of intention, it’s fully possible to start taking the wheel.