50 first dates, for real

"I am fine being on my own," I whisper to myself as I download the app. But I prefer not to be anymore.

50 first dates, for real

“What’s something you definitely want to do this year?” I copy and paste the message and send it to the ten matches in my inbox, which I have accumulated since morning. Bumble has a lady’s ladies-first policy, and this one is on a mission. I feel like a genuine sociopath with my little list, the memes and TikTok’s I send back and forth between a friend, “I want an airport dad!”, mixed with the arbitrariness of whoever I match first with. Romance will have to take a backseat today. This is about sifting through the mud of men who are looking for “nothing serious but want kids” and “do not want to be penpals”.

It’s the last Friday of January, I’ve been crying and condemning my single life all morning, and so I made a plan: 50 (first) dates. I am fine being on my own, I whisper to myself as I download the app, but I prefer not to be anymore. Something needs to change.

I need to detach, I need to find a way to make dating fun again, so I turn it into a game of sorts. If I were a Gen-Zer, I would call it a challenge, and maybe I secretly do. The goal is to have 50 dates this year: worst case, they will be 50 dates with 50 people; best case, somewhere along the lines, I’ll meet someone and fill the quota that way. If dating is a game, I am detached from its outcome, and one needs a special kind of amnesia to enter the modern dating scene anyway.

Because when it comes to hetero-normative dating, the bar is in hell. The recent outrage over Bumble’s celibacy ads, that TikTok 6f5 anthem, the harrowing question: is everyone you’ve ever dated a narcissist? There’s not a lack of information on red/green/beige flags, and yet it seems that modern dating is stuck in a perpetual Groundhog Day or the noughties version of that: 50 First Dates.

In 50 First Dates, Drew Barrymore plays a woman who has a specific kind of amnesia that eradicates her short-term memory. So Adam Sandler, who plays her love interest, has to make her fall in love with him every single day anew. Some days it works, some days not so much.

But it’s the idea that fascinates me. The premise of both movies Groundhog Day and 50 First Dates is that you have to try again and again to win someone over or from the female perspective that you: have to forget all the shit that has ever happened to you. There are lessons to be learned in each encounter. Love is not something that simply occurs but something that must be built. And also that you need to decline every poorly executed attempt. No excuses. Consistency is key.

After texting with various matches, I scheduled the first date for Sunday. I’ve got no time to waste and, admittedly, do not want to be pen pals either. Marc is from New Zealand, and I have a slight issue fully understanding what he says over the bar noises and him chewing his words. We’re meeting for an hour, as I have told him that I will go to an open mic afterwards. The internet has advised me to schedule dates with time limits, so that you do not need to come up with an excuse, and also not to overwhelm yourself with a stranger’s life story. The conversation flows, we both love Saoirse Ronan, who, he tells me, has a flat somewhere nearby. I make him laugh, and the next day I text him and ask if he wants to go for another drink, and he rejects me. I read his message over and over, dissected it for two days with my friends and then came to terms with the fact that if someone rejects you after an hour of talking to them, that person is not meant for you. They simply knew earlier than you did which sucks because they didn’t allow you to find out for yourself but practically they just saved you time. So I let it go and remind myself that the whole point of this dating marathon was to get through it and not to put my self-worth on the line. Dutifully I write his name down behind the number one on my 50 (first) dates list and in brackets (wanker!), choose unmatch and focus on the other people in my inbox.

Currently, there are three that I zero in on, and so I set up dates over the next two weeks. “Is it wise to date multiple people at the same time?” A friend asks me for a beer. “How can you actually get to know someone?”. I tell him about my anxious attachment and how I need to chill. the. fuck. out. – Clearly. And the other truth is, I don’t know how to choose anyone anymore. Photos are deceiving, intros can be flat-out lies, and nobody tells you whether they are over their ex in their bio. Mark Groves, dating coach and person who is regularly flooding my algorithm, says: “If you don’t know your No, your Yes means nothing.” So this is what I’m trying to figure out.

My second date with Luca starts a lot more promising, and six and a half drinks later, I wake up in his bed. As I lie there fully clothed, his hand respectfully wrapped around my waist, I realise how thirsty I have been for touch, to lie there with someone in a bed that is not my own. He almost tripped when he got up from the couch we had been sitting on till 4am. It was like neither of us knew exactly how to move on from talking and making another drink, so we repeated the cycle until we both basically collapsed. He texts me the next day: “I should have kissed you and a lot.”

They say you have to kiss many frogs, however, in the original version of the Brothers Grimm fairytale, The Princess and the Frog, instead of kissing the frog to turn him into a prince, the princess throws the frog at the wall in disgust. Rightly so, I think. Why force herself to believe a frog’s promises of being a prince? Why force herself to share a bed with a slimy pond creature, just because he helped her retrieve a golden ball she dropped? That’s just common decency. So I’m throwing frogs left and right on the wall. See who actually sticks.

The next frog is called Dan, whom I immediately dub the wholesome guy. He’s got his shit together, a great relationship with his parents, he listens and asks questions, which – if you believe the internet is almost unheard of – so this is what we’re here for as I lean back comfortably, listening to his story about how he made pizza the other day. In the first half hour, I keep thinking about how I don’t think there’s any chemistry here, but after a while, I settle in. It’s nice when someone is actually emotionally available, and if the dating coach who sends me weekly emails into my inbox is correct, “the spark is overrated”. After two hours, we hug goodbye, he says he very much enjoyed the date, and I agree to see him again. In the following days, we exchange voice notes where he describes to me in detail what he is having for dinner and how much he exercised that day. I try to make some jokes, I ask some deeper questions, and then I realise that I may be okay without an initial spark, but I cannot for the life of me live without a funny man.

Though I’m annoyed that I seem to find myself in the classic scenario of good on paper, boring in real life, I do understand the difference between giving someone a chance and not being incompatible. And that is the incessant dread I feel when I am the only entertainment in the conversation. But I take note of how he treats me on our second date, the way he makes me feel safe, how he’s good at communicating his intentions and even how he takes my inevitable rejection a few days later: with absolute grace. He might not be the guy for me, but he opens my mind to a new baseline of how someone who is interested shows up.

“50 First Dates? Like that movie?”, a friend asks me as I tell her the latest dating mare of the guy who turned out to believe in pro-Russian conspiracy theories on the fourth date. It’s the beginning of March, and I’m already at date number ten and have just rejected a guy who not only believed in conspiracy theories but also had a habit of writing scathing reviews of every single place he visited, including his local Lidl. “Sounds like something you will write about.”, she comments, and she’s not the only one of my friends who keeps urging me to document my experience. There is such a lust for content on dating, new terms are created every quarter to try to digest the intrinsic power-dynamics of one of the most fundamental needs of humankind: to love and be loved. People creating spreadsheets and yearly reports showcasing their dating statistics on TikTok is just one of the latest trends of an ongoing analysis of: what the fuck did just happen to me? – Though frankly, when it comes to dating in your 30s, there’s no TikTok or Reel that could ever contain the multitudes of horrors one is bearing witness to.

Exhibit A: The guy who texts all the time but never wants to meet.

Exhibit B: The guy who does not ask a single question on the first date.

Exhibit C: The guy who secretly has: a wife/a child/a drug addiction/huge mental health issues and/or lied about basically everything else. Take your pick.

Exhibit D: All of the above.

There is such a lust for content on dating, new terms are created every quarter to try to digest the intrinsic power-dynamics of one of the most fundamental needs of humankind: to love and be loved.

A couple hours later I sit on my bed full face of makeup on and hopes high. Until I receive a text from a new prospect and one of my favourite quotes from Kristin Dombek’s The Selfishness of Others floats through my head, “Why is having a boyfriend or a boss so much like having a personal villain anyway?”. The guy that I was supposed to see in an hour just bailed on me, due to “work reasons”, which I understand but his lack of suggesting another date realistically means: he’s a flaky motherfucker and is never going to text again. Unsure of what to do with myself, I scroll through my WhatsApp chats. Luca, who wanted to kiss me a lot, still sends me messages every day about what he is doing, but never asks how I am. He says it’s because he’s from Sicily and people there wouldn’t ask a lot of questions for fear of prying. Which I do not believe for a second, but because I‘m fully dressed and put make-up on, I make an exception and ask if he wants to go for a drink. He promises to go down on me some other day, as he is already out with his “buddies”, unless I want to see how his evening develops. I decline. All night I think about his proposal for another day and how his offer to go down on me is my Achilles heel, but I have to remember – and this is true – he wasn’t exactly exceptional at it anyway, was he?

The upstairs neighbour is singing Total Eclipse Of The Heart at the top of her lungs, she seems to be dancing as well, because of the stomping noises that accompany her coarse voice. Before that, she was singing Anastacia’s Left Outside Alone, there might be a breakup in session. I sympathise.

On another night, another guy that I’m dating is showing me an old picture of him as a goth. And I wonder why some people outgrow their youthful personas whilst others don’t. His tattoos still give it away. A past that was debauched and full of excess, presumably. Or very lonely.

I explain to him that I used to have blue hair and a nose ring, that I just took out recently. That I used to look adventurous and unconventional. He observes my hands and my long fingernails that I’ve started to grow. I catch his look and the assumptions he is making. I feel an urge to explain myself more, but I stop. I guess this is where meeting people from the apps feels so fatal. We start with no point of reference for the other person, no friendship group or workspace to connect to them, no other habitat that would tell us a little bit more about them. Everything has to be verbalised, asked for and believed.

You could be sitting in front of anybody.

Then I’m ill for three weeks, and everything comes to a halt. I binge One Day and find the female character Emma incredibly judgmental and obnoxious, and sadly, I have to admit she reminds me of myself. Asking someone who they want to be when they’re 40 during a one-night stand is something I might do, too. My love language is talking someone tired.

I sent a test balloon to the former goth guy. Our third date ended on a weird note, between admiring the architectural structure of the door of my house and the words “keep in touch?” or was it “keep in touch.” I’m uncertain now whether there was a slight rise at the end of his voice, indicating a question mark or a full stop. A continuation or a halt. Sending a test balloon is a German expression which means something along the lines of: this message is casual enough to mean nothing but meaningful enough to represent something.

It should be a continuation of the conversation as if to say: oh this thing I forgot to reply to. No hard feelings if it gets shut down, goes unanswered or finds itself stuck in a tree.

The art of choosing the right test balloon is fickle. Just below the too intense, I saw this and thought of you, it lives in the territory of internet links and memes. Luckily, I have the perfect test balloon. A link on how to read War & Peace, as he mentioned he was about to embark on this noble quest to read what, depending on the translation, could be a book of 1300 to 1500 pages. Smugly, I send it and pretend not to wait the whole day for an answer. When he finally does, I realise that the problem with even the best test balloon is that if the answer to it is just: “Thanks :)”, there’s no rule for that. You will have to wait it out. And let time give you the answer. Or in my case: the tarot. I draw the Moon: two dogs barking at it, the face of the moon is in agony, trying to distinguish, trying to think. It’s a very accurate depiction of how I feel. I always do this, I have this urge to close the gap where the other person should act, compensating their lack of action with doubling down. As if they were somehow prevented from showing up, as if I had not already made a move. Always barking at the moon, waiting and hoping. Barking louder and louder. When the truth is: if someone’s interested in you, they will make it painfully obvious.

The former goth guy is fizzling out his texting, but I prefer a sudden death. No more test balloons that get caught in the trees of confusion, so I text him if he wants to meet up again, and he finally admits that: he has already met someone else. And I notice that it takes about four days after a rejection for me to actually think rationally about the situation. It’s not an exact science, but it’s something I hold onto for dear life when I’m at desperation station, where my head tries to convince me that this particular person is the last chance I’ll ever get at love. He is not. He was simply date number ten to thirteen. And I have 37 more to go.

“What is meant for you will not pass by you.” I hear the sentiment echoing all around me, partly because I keep repeating it to everyone all the time. I need to believe it, as dating in your 30s and beyond is just so much harder. Unlike people who fell in love in their early 20s, who were lucky to not go through the experience of serial dating or long single stretches, we are still out there, with all this baggage now and the disappointments, the heartbreaks; and we still show up and say despite all that: let’s try this again! Like little romantic soldiers, we march on, because for us, love truly is a battlefield.

Date number 14 texts me that he took care of the reservation, which I immediately screenshot and send to multiple friends: Finally Airport Dad! He chose the location, the time and picked me up from the tram station as every well-organised and capable airport dad would do. As he sips his beer, he tells me about the time he left the army to study international politics, how he has no real connection to his family anymore and how I wouldn’t find him on the internet, but that doesn’t mean that he killed anyone. A joke, of course. When the bill arrives, he crumbles it up in front of me. The lady is not allowed to see the bill. He asks if I want to go for another drink some other place and I accept because I want him to be airport dad but the way he is stretching his neck every ten minutes, his tense muscles, something feels strange and I am unsure whether I am still here because I find him interesting or because I am slightly terrified.

Like little romantic soldiers, we march on, because for us, love truly is a battlefield.

Later on he will tell me that blondes are his type, and that will support the slow suspicion in my gut that something isn’t quite right. First of all, having a type is something that 15-year-olds do when they rank their classmates’ hotness during gym class. Certainly, everyone has things that they usually find physically attractive, but don’t tell your date about it, it makes you look shallow because that’s what it is. And you can’t really win either because if you say someone is your type, that person will think, that’s all they are to you, and if you are not their usual type, then they’ll always look at the people around them who are in comparison. But I guess some people do enjoy making their dates feel insecure.

As I sit on the tram back home, I try to figure out how I feel about the guy. Dissecting my fantasy of airport dad and the reality that presented itself. I come up with excuses, I convince myself that it is all in my head and that I am just nervous, and then I notice how scared I’d be to reject him, to craft that text and call it off. And this is how I know: I didn’t feel safe with him at all.

“I think you just know. Everyone I’ve ever liked, I knew pretty much in the first ten minutes of a conversation.” There’s nothing like dating advice from married people, I think, as I listen to my friend over coffee, but I’m starting to agree with it. I tell her about my concept that the first date with someone from an app is basically date zero, a pre-date to figure out if you would even want to go on a real one. As you don’t have that time to look at them from a distance or be in their vicinity casually for months, like at work or other places where people could meet each other regularly. It’s an attempt to reverse engineer the mystery and space it actually needs to figure out how you feel about someone. Sometimes, of course, that mystery and space is not needed when you have to sit through three hours of a lecture on how nuclear power plants work, as date number 15 proves. I thought the internet had done its work already and spread the gospel of the man who doth asketh nary a question on a first date, but I’m here to confirm that that man is still very much single and has no idea why. The next day, he texts me how much he enjoyed the date and if I wanted to go on another, so I do him a favour and send him some reading material to catch up on. Wtf? he texts five minutes later. A question, at last.

There are more elegant ways to reject someone, but between blocking, ghosting or slowly fadin,g I do prefer an honest word. “That must be because you’re German.”, the next guy will attest me. We go for an hour-long coffee walk, with the vibe of being stuck in a corner with someone at a networking event. Which I assume to be the mutual experience as we silently stare into the void over our coffee cups, so I am baffled and kind of unprepared when he looks at me at the end and says he would like to do this again. I’m reminded of Marc from New Zealand, the first guy I dated and think what a funny turn of events to be in his shoes now. “Honestly, I don’t. I respect you and I think you’re a great guy, but I don’t see this going any further.”, I hear myself utter. His face crumbles slightly, but I know he’s going to be fine. I just saved him a lot of time.

Initially, I was hesitant to write about all of this because even though dating stories are hilariously entertaining, I wanted to be in it. I didn’t want to already think about how I would craft all of this into an essay as I was going through the motions. I didn’t want to do it for the story. Precisely because dating is full of storytelling and fairytales that get in the way. What I wanted was to sit down in front of someone and find my equal. “I think when you are truly stuck, when you have stood still in the same spot for too long, you throw a grenade in exactly the spot you were standing in, and jump, and pray. It is the momentum of last resort.”, writes Renata Adler in Speedboat. The list was my grenade, it set something in motion that otherwise would have stayed stuck. It forced me to move on, both feet jumping: I’m in it, I’m in it, I’m in it.

It’s the end of April, and I make a wish, tying a ribbon around a branch on Calton Hill. Every year, people assemble on the hill right in Edinburgh’s city centre to celebrate Beltane, which is commonly known as the fire festival, to welcome the change of the season to summer. A potent night for love and fertility if you believe in pagan traditions. The next day, I go on date number 17, and a few days later on number 18 and 19 all the way to 34, writing the same name over and over again, till I forget to count the dates, till the list becomes obsolete – because we’re in it.

---

Who wrote this?

Sophia Hembeck is a writer and cultural critic based in Edinburgh. Parts of this essay are excerpted from her recently published essay collection Things That Are Different Now. She writes a weekly substack called The Muse Letter where she wonders about the meanderings of life.