The Enduring Loneliness of Searching for Love in Your Twenties

Why I no longer believe in the benefit of a doubt

Alexandra Miller
Ascent Publication
8 min readDec 27, 2018

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Most of our unsuccessful experiences seem to follow patterns that ring true for strangers online. It has become so difficult to find sustainable relationships that we have since developed a meme culture of young men and women remarking on the predictability of Tinder dates, the exhaustion of short-lived romances, and the dependability that you will be treated a specific way by specific “types” of people (and the ensuing disappointment, but not surprise — you will face when this occurs.) To simplify the general consensus of dating woes in my experience, and boil it down to gender from one woman’s perspective, women seem to be burned by an abundance of “emotional unavailability” while performing emotional and sexual labour without the benefits of the relationship label. This allows things to comfortably fizzle without a formal breakup which can be mutually beneficial to folks who don’t really have a connection. But it also allows men with multiple partners a socially acceptable passage in which they aren’t required to disclose this information to the women he’s seeing. It also condones “ghosting” when there is a loss of interest or in my experience, one of the women is starting to veer toward requiring relationship-like maintenance.

I argue that this tenant of modern dating is exploitative.

The performance of ambivalence in dating has become so routine that to experience any kind of romance or respect from a guy is now its’ own red flag.
I have had difficulty translating my modern dating melancholia into a profound memoir in order to give me peace of mind. Writing about one’s disenchantment with the world can make it more digestible. But as I spend my free time pondering the new and awful turn modern dating has taken I still find myself falling hopelessly into optimism that things will get better. Perhaps after my last text was ignored by my most recent Lothario, I have finally been gifted the amount of male ambiguity I needed to finally be fucking skeptical. Or I will just continue dunking my cookies in Dumb Bitch Milk.

My story starts the moment I entered the dating world from the couch of my college dorm. After postponing University for a year I downloaded Tinder on a whim after hearing my roommates participate in all kinds of sex while I scrambled eggs. I was desperate to lose my virginity. Unfortunately for late bloomers, this desire grows out of embarrassment and curiosity rather than through libidinous desire. Not wanting it to be with someone I wasn’t comfortable with, I had convinced myself it was entirely possible to find a boyfriend on these apps by simply going with the flow and completely hiding the fact you want a boyfriend.

On and off throughout school, I went on sporadic Tinder dates. These usually played out unromantically — we pay for our own drinks, there’s minimal flirting, lack of physical affection. We would part ways, absent was a text follow-up from either party, and I would forget about the experience in a week. I certainly expected a little more wooing (had these guys expected anything from me) and quickly learned that dating etiquette from the Nora Ephron films I watched was either completely romanticized fiction or just not exercised by the types of guys using dating apps.

I relegated my first dating experiences to simple mutual unattraction. Lack of physical affection made these easier to write off and made for funny fodder with friends. Contrary to my theory that romance was for people who meet organically in coffee shops and book stores, my demeanour (retrospectively… virginal) was the culprit for my lack of success. Aha! The key was not to make it too “challenging” by Tinder standards — action with minimal effort. Act experienced without being easy, wait but don’t hold out too long, come off ambivalent about the potential for what this could be without seeming like you could care less. Walk this tightrope to success.

Going forward I became more comfortable with my sexuality and femininity and through boredom developed a desire for companionship. Following university, the intensity of my interactions with men increased, the duration of which did not. My first hook up was with someone I had been trying to date for over the period of a couple of months. From the beginning the signs his interest was primarily shallow were quite apparent, signs I mistook for coy dating rituals. Like most women trying to keep their ego intact, I dismissed the ambivalence shown toward me and I went through with a hookup. My hopes were dashed when I received my first crushing “you’re groovy but I’m trying to reunite with my ex-wife” message. I left my feminist law class crying. I told myself that I had sold myself short and jumped the gun on sex. I was now convinced that if I wanted both intimacy and a sexual relationship I would have to sacrifice my own physical desires in order to market myself as a girlfriend type after initiating a “chase.” Theoretically, this should work with men I met in person if the sub context of tinder was off the table.
Where this became more challenging for me was when I, like most people, began developing my sexuality. Not only was I experiencing my own sexual impulses but I began to feel as I was at the behest of male sexuality during and after dates. The phenomenon of getting my dates’ off while either not getting offered pleasure, declining it out of lack of comfortability or experiencing lackluster attempts at sex made me feel increasingly like the intimacy I so craved was becoming polluted by hookup culture. I consistently felt spent and sold short after dates and like my indulgences were working against me in the search for a partner.

Following the ex-wife fiasco I started to pick up on emergence of the emotionally-unavailable from a slew of other guys I dated in 2018. Aside from coincidentally-but-most-often-out-of-lack-of-ingenuity — wearing the same outfits, telling the same jokes, and more often going to the same spots, the softbois I dated had an almost mathematical interest in me. Heightened interest when I’m a concept; an Instagram mutual, a face on Tinder, a co-worker. Piqued interested when I’m someone who takes them to a dive bar and shows a dry, dark sense of humour, or my interest in “niche” music. Mediocre hook up. Gradual withdrawal. Complete and total loss of interest. Sometimes God sprinkles the sadism of social media stalking on there to prolong the withdrawal or “ghosting period” (and depending on my level of interest prolonging my mourning period.) This cycle translates to when I’ve slept with someone off the bat, waited a couple of weeks, and waited a month. Each time I date someone I wait longer to see if maybe the waiting is the problem.

Friends try and discourage my overwhelming belief that I may be the culprit. “It’s the softboi cry-babies!” they decry “try dating normal functioning human beings.” I defend my softboi cry-baby because he drew my dog on my arm and it was cute and I liked it and for a moment I felt the intimacy that I’m hesitant to let go of. But they’re right. Most of the guys I was lucky enough to have shortlived “romances” with rejected me in familiar patterns. Most of them had recent-ish exes, some of whom shared leases together, wanted something casual (whether this was discussed initially or not), and were… yes, artistic types. I assumed getting involved with sensitive men they would be sensitive to my feelings, but it turns out this genre is more sensitive to their own feelings than those of the collateral damage they accrue cruising for sex.
At first, I doubted my sexual abilities and resented my body. The painful time from me putting myself out there and initiating a conversation or another date — to the time it would take to read — to the time it would take to respond, were all excruciatingly painful after knowing someone has seen your vulnerability — in the crude naked sense. I chalked it up to not having worked out in a few days, indulging in too much food while we were together, the way I looked when I ate, what I ate, maybe even what I look like in the morning? The loneliness mixing with the soft rejection forced me to examine the parts of myself with a microscope I had been conditioning myself to accept as young women do when they overcome the trauma of being a teenager. Overlooking someone’s red flags and lowering your standards and THEY have the nerve to reject YOU? Self-hatred amplified.

Where my friends are wrong however is the suggestion that the cavalier disposal of women is native to the sensitive artist type. “Dating culture” is chock-full of all types of men who, under the guise of being damaged from their past, rack up your emotional mileage and then skip town when things veer too close to being serious. Men benefit from emotional and sexual labor while reiterating the boundaries of whatever this is — without of course really identifying it as anything other than a friendship. And adults know very well this is not friendship. Thus when they ghost you or feel compelled to date around, they’re not really a bad guy and you’re really just asking for too much from them and that’s not fair of you.

The last guy I dated made little effort to see me outside the confines of our set-up. When he was with me, he acted like he liked me and treated me like a girlfriend, and then when we weren’t together I never heard from him and it was almost as though it hadn’t occurred. Phantom boyfriend syndrome. After we had sex his growing distance around me was palpable and I felt myself trying to give him space without losing him. This made me push myself on him further. When I offered to make him dinner while he was sick, the way he declined made more than clear that I had crossed a boundary of our “friendship.” I cornered him as to why he was starting to withdraw from what we had, and he came back with a familiar “we’re friends and this is why I didn’t want to have sex with you because you want a relationship and I don’t.” Once again I was being told what I wanted by someone who, while being upfront about not wanting to date me, had violated his intentions every time we were together.

Why bother then with this charade? In my experience, modern dating is a façade for self-interest and blatant disregard for others. Women maintain optimism in the potential for love that comes rebounding after experiencing the ambivalence and thoughtlessness of dating. I keep trying to reinvent myself and my techniques as I’m reminded that this is just the reality of dating in your twenties and something worthy of my time will come soon. But I’ve come to the realization that I am doing something wrong. The facts display that these men simply aren’t looking for something from me that I’m looking to give and I have consistently denied red flags in favour of fleeting intimacy. Women need to take up an issue with the blatant disregard for others and leave. Recognize when you’re misconstruing a meaningless hook up from someone else’s perspective for meaningful intimacy that temporarily fulfills a void in your heart. Stop giving emotionally barren men the opportunity to exploit you by donating them the benefit of the doubt. There is a window of grievance with relationships and if you think their window should have expired by now they should not be dating. This person’s absence from your daily life and you from theirs is exploitation of what you have to offer.

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Alexandra Miller
Ascent Publication

Neurotic. Published in the Writer’s Guild and The Ascent.