A reflection on my experiences in modern dating — optimizing apps, defining relationships, and reconciling emotions.
Netflix Without the Chill
In the summer of 2017, I had a friend that I was completely enamored with. We messaged every day and had crossed the Berkeley-SF divide several times to platonically ‘hang out’. But I wanted to take things to the next level. Confident that she also liked me, I drew on my several months of dating app experience and approached it the only way I knew how. I proposed the tried-and-true method of watching a movie together under the influence, assured that something would happen through the unspoken expectations of Netflix and chill.
Magically seducing her did not go as planned. I realized too late how high the stakes were — she wasn’t just another Tinder hookup, I actually really liked her! I ended up sweating bullets in silence through 169 minutes of Interstellar (I don’t know why either) before blurting out during the credits, in my mentally-compromised state, fun bits like ‘do you like me’, ‘are we dating’, and ‘what are we’. This promptly induced a panic attack in her, an Uber ride home, and a swift end to any chances I may have had.
Thankfully, we can laugh about this today as friends. But it wasn’t just a lack of experience that kept me from properly expressing my feelings that night. In the years since, I’ve come to realize just how much modern dating dynamics have shaped my approach to relationships. Apps opened up limitless potential, but quickly became dehumanizing when I leaned into transactionality and efficiency. In doing so, I also became desensitized to what mattered — emotional honesty, communication, and a willingness to be vulnerable in spite of deep-rooted fears of rejection and loneliness. These are topics I’m still grappling with today, but I’ve learned some lessons from all the funnels and FWBs along the way.
Into the Fray
My journey into dating happened quite late. Throughout high school and college, I was a complete nonparticipant in any kind of romantic endeavors despite being surrounded by school romances. I was also laughably oblivious to even overt advances.
Post-graduation, I had a period of serious regret as I adjusted to the social shock of entering the ‘real world’ and realized the prime dating opportunities I had passed up in college. After a few awkward romantic stumbles more befitting of gangly teenagers than the Real Adult™ I was supposed to be, I fell unexpectedly into a deep, year-long relationship with a college acquaintance. When that petered out, I semi-jokingly declared to my friends it was finally time for my ‘hoetation,’ my chance to dive into the world of apps and casual dating and make up for lost time. Needless to say, I had no idea what I was getting myself into.
By now, the transactional, commitment-phobic nature of modern dating in younger generations has been discussed at great length. Plenty of new variables influence the increasingly online dating experience — rising expectations to have a ‘soulmate’ who is your perfect lifelong match and not just a partner, the way our dating pool has scaled exponentially to encompass people from all over the world, the impossible exercise of compressing a representative slice of your humanity into six images and 500 characters, and our persistent but faulty belief that filtering by surface-level criteria is a good predictor of who we will have chemistry with in person.
With this new system of online dating comes new ways to optimize it. I’ve found this especially true in the young, techie, efficiency-oriented realm of San Francisco, where yuppies try to stuff courtship into overbooked social and work calendars. As engineers and business people who already build mental models for complex systems and struggle to keep work from blending into personal life, it’s unsurprising to see how many of us optimize dating as we would any other work process.
For example, because the onus is typically on the guy to initiate conversations with matches, I know several friends who have A/B tested different openers and tracked results in spreadsheets until they’ve found one with the highest response rate to copy/paste. One time, a fellow Uber passenger boasted to me about the chatbot and learning model he had built to auto-generate phrases for new Tinder matches. (He owned an AI startup, of course.) Other friends systematize the most time-consuming step, first dates, to make them as efficient as possible, running their date prospect through a standard set of locations, topics, and stories, like a salesperson going through their playbook, until they can close the ‘deal’ and secure sex, or another date to get there.
I’m guilty of this too. While not quite as intense, I did at some point grow tired of trying to craft a custom, thoughtful message to every match only to be repeatedly ignored, and tried out a dozen or so opener ‘templates’ that I tweaked based on each profile and tracked the success rates. Better than just sending ‘hey’, right? My product manager side also got the better of me when I created a kanban board in Trello, a project management tool, to track my app matches. Swiping, chatting, and planning dates for dozens of people simultaneously was wholly unfamiliar to me, so I approached the challenge the same way I tracked work and personal to-do lists. This elicited responses from friends ranging from amusement to concern that I was exhibiting high-functioning sociopathic behavior…
But when I asked a friend who had been ‘in the game’ longer for advice, he referred me to Hacking Sex, which described dating as just another funnel. In business, a marketing funnel describes a customer’s journey to buying your product: the customer first becomes aware of the product, considers it to solve their unmet need against alternatives, and then converts into a customer when they purchase it. The process is depicted as a funnel because the number of people that make it to each subsequent stage drops off, and entire departments are built around driving as many people as possible through to funnel conversions.
This basic framework can be applied to the dating realm too, except with people as the products. You market yourself on apps with a pithy profile so people are aware of your eligibility, get your matches to consider you against thousands of other people with dog photos, relevant memes, and witty banter, and then finally convert them through dates to whatever end goal you’re looking for — companionship, sex, a relationship.
This goal-oriented model appealed to me after my initial dating struggles. I hadn’t made much headway with finding anyone I liked enough to date or even sleep with, and was tired of trudging back home deflated from painfully mediocre first dates, repeatedly going through the hassle of leaving work early and fighting SF happy hour crowds for the privilege of paying $70 for four cocktails with someone I was never going to see again. That’s what dates were supposed to be, right? At times I felt like I was just being used to dispense free, overpriced meals and drinks.
The idea was that if dating is a numbers game, why invest so heavily in someone when there are such low odds of someone making it through the whole funnel? When there are plenty of fish in the sea, why not text the bare minimum necessary, propose a quick, copy-paste first date of a coffee, drink, or ice cream to gauge chemistry, find out upfront if I was getting catfished, and be ready to move onto the next person? Lower your expectations and just go on more dates, my friends told me.
While this approach helped get me through a higher volume of matches, it gradually burned me out. What first started as a way of saving time grew into a sense of disillusionment and a more insidious form of dehumanization. As I depersonalized dating, matches merely became ‘leads’ or ‘prospects.’ Individuals became interchangeable, names of failed first dates or disappointing hookups were quickly forgotten, and even the act of dating increasingly felt like a second job processing an endless assembly line.
I had streamlined the operations. But the sad truth was that the more market logic I applied to dating, the more desensitized I became to my emotions as well as my dates’. When someone only manifests as an icon and a few chat bubbles, with no social repercussions of being in your friend circles, it’s standard practice to ghost and be ghosted. I didn’t dwell on feelings, this was the nature of the game. We all have more in the pipeline anyways. At least they got the free drinks, right?
Tiers of Commitment
This mindset in modern hookup culture inevitably leads to what the Hidden Brain describes as an implicit ‘race to the bottom’ of commitment. Whoever cares less, wins. The less invested you are in someone, the less likely you’ll be hurt. It’s a clear takeaway — maintain as much emotional distance as possible.
This is true when we already look at ‘sourcing’ dates through the lens of a sales pipeline, but the modern dating scene isn’t quite as black and white as either meaningless hookup or committed relationship. Even if you make it past the gauntlet of matches and first dates, convert your ‘lead’, and start ‘seeing’ someone, the complexity of modern dating doesn’t end there. There’s a full spectrum of gray in between a one-night-stand and an official relationship, fuck buddies and friends with benefits (FWBs), exclusive and non-exclusive dating, and even debates over what it actually means to ‘date’ or ‘hookup’.
These tiers of commitment are ambiguous and non-linear. You might dabble in just one stage before breaking things off, inadvertently stumble forward or backward in a long-winded path to becoming ‘official’, or skip the games and jump directly there. It’s increasingly common to avoid applying a label at all and say ‘oh we’re just hooking up’, ‘we’re just seeing each other’, or probably the most frustratingly ambiguous ‘we’re hanging out’, all of which connote less seriousness than actual dating. When not discussed, you’re each left with your own interpretation of an invisible social contract.
For example, when I was just hooking up with someone, should I also have let her sleep over and risk stoking unwanted feelings? Was going on 1:1 dinners with an FWB too date-like and giving the impression of being something more? If I wasn’t ‘officially’ dating someone, was it weird to invite her as a plus one to my company party? If my friend had defined exclusivity but wasn’t formally dating someone, was he morally corrupt for wanting to platonically ‘hang out’ with someone he may have been interested in? What about swiping on the side, if he never actually met up with matches?
As you can imagine, this attempt to disconnect sex and companionship is far easier said than done and opens up a whole host of opportunities for feelings to be hurt. There’s a baseline level of maturity required to really be self-aware of your needs, and I often set boundaries in an attempt to control my feelings, rather than reflect what I wanted.
More often than not, we push off addressing these questions until the dreaded ‘DTR’ (define the relationship) conversation, which doesn’t get triggered until after boundaries have already been crossed, or someone finally ‘catches feelings’ and can’t keep them suppressed any longer. I didn’t even bother with such discussions initially because of how utterly terrible I was at them. My first attempt led to that less-than-stellar Interstellar experience, but in general, I found the idea of directly asking someone on a date wholly unnecessary. It was so much easier to just ‘hang out’ with someone I liked until I had an excuse to invite them to a Temple SF outing or 1015 Folsom concert, bludgeon my social inhibitions into submission with enough $16 AMFs to drunkenly hook up, and then figure things out from there. Why force a conversation when you can just drink and ‘let things happen naturally’ instead?
A Ceiling to the Floor
In my circles, I don’t hear as much traditional bravado about counting ‘notches on the belt’ and such, but I’ve definitely noticed subtler forms of toxic masculinity. It shows up insidiously in the language we use. Someone who wants to pursue a long-term relationship is jokingly described as ‘settling’ or ‘retiring’, an evolution of the classic ‘tied down’ that also connotes giving up in some way.
I’ll hear ‘catching feels’ in contexts like ‘stop hanging out with her so much dude, you’ll catch feels’ and ‘catch flights not feels’ accompanied with a plane emoji, which, while often in jest, also normalize noncommitment. Even the phrase ‘catching feels’ itself makes human emotions sound like they’re STDs. Something to avoid as much as possible and address only if there are no other options.
The language around dating has morphed in other ways too. When I lamented to a friend that the person I had been seeing for six months broke up with me, her first response was ‘wait, I thought you weren’t actually dating?’ My mistake — you don’t ‘break up’ with an FWB, exclusive or not, you ‘stop seeing’ them. It implies a passive return to the norm rather than an explicit decision to end something, like the way you might say ‘I stopped using ClassPass after the trial’. It wasn’t real, it was just the end of a trial, so why be sad?
While I’m sure there are people who genuinely have no interest in ever dating seriously, I know now that my detached, avoidant attitude towards dating was self-defense against being hurt. Even when I eventually learned to establish mutually beneficial FWB situations, it was hard for me to admit when I wanted more from the relationship. It may have been anxiety-inducing to not know whether my feelings were reciprocated, but bringing up DTR conversations could be even more stressful.
They’re by nature kind of awkward, as it can be strangely procedural to walk through a list of needs like you’re setting up a contract for sex and feelings. This, combined with low self-esteem and an inability to be honest with myself when I wanted something more meant I rarely brought them up. A desire for peace of mind had to outweigh my fear of coming off as needy or insecure, of being rejected. Worse yet was the risk of actually dating, failing the relationship, and losing a friend and the ‘good thing’ that we already had. Better to leave it as is.
If you have loss aversion and don’t trust yourself to make a relationship work, you downplay what it means to you with business terms or some ambiguous label to signal that ‘it’s not that serious’, and you don’t need to DTR, regardless if that’s true. If you don’t want being ghosted for the 30th time to hurt, you tell yourself you didn’t care about that one anyways. Instead of confronting the vulnerability that comes with relationships, it’s far easier to build up more fallback options, more leads, to shield yourself from rejection and inevitable loneliness.
In this way, it’s almost like we’re trying to create plausible deniability when relationships end, an attempt to minimize the loss, the pain, the need to investigate our emotions any deeper. Just keep your head up and move onto the next one, right? But does it really hurt any less just because you called the relationship one word instead of another? I’ve done this a few times now. I can assure you that breaking up with someone you’re emotionally invested in hurts, regardless of the label you use.
If delaying commitment is an attempt to mitigate the ‘downside risk’ of pain, are we also limiting the upside of what we could have gained in a richer relationship? Does implementing a floor to your sadness also create a ceiling on your happiness? I used to think about the opportunity cost of being ‘locked in’ from dating a single person, but what about the opportunity cost of not committing more? How much richer of a relationship could I have had with someone if I had given it my all instead of holding back, unwilling to be fully vulnerable, and put my happiness in their hands? Are these optimization exercises we engage in to minimize hurt and maximize odds yielding what we truly want?
Conceal, Don’t Feel
When I discuss this with friends, responses range from ‘well this sounds awful, what a terrible time to be single’ to ‘at least you GET matches, or don’t have to deal with fearing for your personal safety on dates’ and ‘why are you so sad Patrick, chill out lol’. It’s not all bad — I’ve left out all the healthy, noncommitted dates I’ve enjoyed, the breadth of life stories I’ve heard, the cross-Europe whirlwind Tinder romance I shared, and the times where I did have candid, mature discussions that grew my capacity to feel.
And as embarrassing as my dating blunders are to look back on, I regret very few, as I’ve found them invaluable for building self-confidence and self-understanding. It’s those mistakes that taught me the value of communication. It was my attachment to systematizing dating apps that made me realize I used them as a shortcut for external validation instead of addressing my insecurities through healthier means. Whenever I was lonely, I was conditioned to open my list of matches or my stupid kanban board the same way we mindlessly swipe through our Instagram and Facebook feeds, more interested in the quick dopamine hit of affirming that ‘yes, people are attracted to me!’ than building an independent sense of worth or genuinely connecting with people I wanted to be with.
I’m by no means a hopeless romantic or love guru now, but if you’re getting into apps or any dating situation, my advice is just to be really honest with yourself first about your needs, and then communicate them (mind-blowing I know). If you like someone, learn to tactfully express it. Emotional connections should be celebrated, not suppressed as liabilities. Instead of trying to prevent painful romantic experiences from ever happening, accept that they’re fundamentally part of the human experience, and overcoming them means learning to live life more fully. And if you’re burnt out or down from dating, don’t just masochistically forge headlong into your backlog. Recognize your pain and take care of yourself.
This reminds me of ‘meeting your emotions where they are’ in mindfulness practice, where you notice and sit with feelings that arise, without denying or becoming mired in them. And if you’re not keen on meditating, just think of Inside Out when the girl finally allows sadness to do her thing, cry, and reach out for support. It’s a wholesome, kid-friendly Disney movie but plenty of adults, myself included, fail to apply this simple lesson when we paper over feelings of loneliness or inadequacy with rebound swipes and self-delusional lies about who we like. ‘Conceal don’t feel’ didn’t work out for Elsa either, remember?
And if you genuinely don’t know what you’re looking for, that’s fine — I certainly didn’t in the past, but make that clear! It took me years to develop a semblance of emotional competency, but ‘I don’t know what I’m looking for’ is no excuse to mislead people. If a systematic approach to apps helps you, go for it. Just make sure you aren’t shoring up your own insecurities at the cost of dehumanizing others. Being honest about feelings, while incredibly hard, spares you pain down the road. And while the rituals and vocabulary of modern dating may have changed over time, the core human needs for respect and acceptance have not. Oh, and try to not give anyone a panic attack.