♥ ♡❦
Good morning friends and lovers. I hope you enjoyed our last letter, (Actually) Unique Date Ideas, which included some fun and challenging ways to break free from the repetitive early-stage dating cycle.
A total of ONE reader responded to let me know that they suggested a grocery / errand date for a Sunday afternoon [4th date]. The suggestion was well-received and the date was a success! The reader liked that it turned a chore into an outing to look forward to. Since they were already quite comfortable with the other person, the lack of formality went off without a hitch. They also learned that their dating partner loves meandering through aisles, and is therefore quite slow at grocery shopping and comes out of the store with all sorts of nonsense that wasn’t on their list. We love these little discoveries :)
Just that one response made writing the letter worth it. Keep em’ coming!
Today we’re addressing the elephant in the room: THE F*CKING APPS.
Love em’? Hate em’? Probably somewhere in between? This is a nuanced topic that rarely gets treated as such. The overwhelming sentiment, according to in-depth cultural research (memes) is that we’re all miserable. The big 3 apps (Tinder, Hinge, Bumble) are seen as superficial, unromantic, greedy, inconsistent, and time-consuming. This Forbes article, the “great deletion”, the ascendance of run and dinner clubs… the list goes on.
Pretty much all the complaints against the Big 3 are valid, but imo we don’t need to hear them anymore. I’m not in the habit of defending tech CEOs, and the way they’ve monetized these apps to make them near-useless for free users sucks, but to be fair, the creators of these apps had a tough job. Dating & relationships are a central component of human life. More important, for many people, than our diets, or where we choose to live. It should never have been expected that the first (second, or third) attempts to capture these complex processes through apps would be a glowing success. Not to mention that the majority of couples around us do owe their meet-cutes (minus the cute) to the apps. There are improvements to be made, but we can’t say they’re doing nothing right.
As serial complainers about the apps (I was once firmly in this category), perhaps it’s time to take a hard look at our personal approaches to dating rather than scrutinizing their sus algorithms, or overhauling our profiles for the 100th time. Ask yourself, fellow complainers: why are we continuing to rely on the apps as our primary tool for meeting new people? Our generation is supposed to be about setting boundaries, letting go of what doesn’t serve us, etc. etc. To have relied on the apps for years with little to nothing to show for it, makes us at least as guilty as the apps are for our disappointment. They shouldn’t be our main tool. Simple as that. They can be a tool — but not the primary one.
Most of our complaints about the apps have the tone of throwing our hands up and lamenting that our generation was given a raw deal. But let’s be honest — our dating pool in 2025 is the biggest it’s ever been in the history of… humanity. I used to complain about too many options, but have since accepted that starting with abundance and shrinking down beats starting with a limited selection (e.g., the 3 ‘nice Indian girls’ my mom DM’d me on LinkedIn) and having no opportunity beyond it. Abundance is a good thing, it’s just that the swiping apps were a bit too broad for me, personally; I was casting too wide of a net. So I set the apps to the side and started intentionally trying to grow my IRL dating pool with filters that brought in more quality + intimacy, while ensuring that I was still meeting enough new people to give myself a chance. For the rest of this letter, I’ll outline how I’ve started making these changes in my life, and how they might be brought into yours.
Cast a Smaller Net Online, or a Wider Net IRL
One way to do this is to pay a steep fee to the apps to improve your filtering options, and to use the filters well. But there are plenty of real-life filters that will work just as well, if not better, than swiping filters, while making your life more social, challenging, and fun. If the apps are your primary tool, there’s a good chance it’s because your social life cannot be described per the above, and that you’re not meeting enough like-minded people as a result. This can be changed by adjusting the filters on how you spend your time.
So let’s think about how most of us split up our time:
Working
Seeing friends + family
Doing our favourite activities + hobbies
Did I miss something? The above three items might make our lives sound shockingly simple, but our decisions around each are full of nuance and, more than anything else, are deeply representative of who we are. Much more so than the superficial filters we use on the swiping apps. All three should therefore be relied on to meet new people — and not just single people, the keyword is like-minded people — wherever possible.
I should mention that for the latter two, friends + hobbies, there is a generation of new dating apps (including Cheers) which help you meet singles through mutual friends and/or mutual interests. I’m not aware of one for the workplace… probably for the best lol. It’s great to see new apps improving on the current approaches that people are clearly tiring of, and making use less superficial qualifiers than the swiping apps. These apps are worth exploring, especially as they grow. But back to casting a wider net IRL.
On the side of working. Do you have a hybrid office but work at home out of convenience? Are you exclusively seeking remote-only jobs? Do you skip work social events so you can squeeze in a workout before dinner? I hear you, but… maybe stop that. Workplaces are v underrated resources for meeting people. Where else, outside of school, will you be surrounded by others with broadly similar interests and intellectual abilities, with endless excuses to get to know them? Perhaps you’re squeamish about the idea of finding love in the workplace (to which I say bring back the office flirt), but that doesn’t matter. The goal is to be constantly meeting new, like-minded people — single or otherwise. And if you think you’re too good / cool for the people you work with, this attitude is probably harming your broader ability to meet new people, both inside and outside of work.
On the side of your existing social network. Put your besties to work by having them constantly on the lookout for you (they probably already are) and actually listen to their suggestions. Also, for the single besties, get them reading this letter so that they are maximizing the social opportunities, which you can benefit from. But more importantly than focusing on your closest friends, normalize the friend date with people who are not besties.When you’re surrounded by your clique, it closes you off to meeting new people. You enjoy the company of those select few too much to take a risk on someone else. Think about that friend of a friend, or person you see around at parties but don’t really know, who always seems to be doing cool shit. Instead of (or perhaps in addition to) DMing hot strangers on Instagram, DM that person — again, it doesn’t matter if they’re of romantic interest or not. Set up a friend date. Keep reaching out across your friend pool through mutuals. Aim for a couple new-friend dates a month. The like-minded, single people will follow.
On the side of your favourite hobbies + activities. I see a lot of people flocking to run clubs. No hate on these, but I refuse to believe that this many twenty-somethings consider running to be one of their preferred hobbies / activities. I think a lot of people are hearing that they are where singles congregate, and it feels like the path of least resistance as they try to wean off the apps. But the path of least resistance is not necessarily the right path. What are your hobbies? Reading? Go to book openings at trendy book stores. Do you find the people there intimidating? Good. That’s what you want. Love to travel? Take in-person language or dance classes from the country you’re next visiting. Cooking? Start a dinner club where you only invite one other foodie you know, who is allowed to invite one person you don’t know, who is allowed to invite one person… and so on. If you live in NYC (as almost all our current readers do), there are outlets + companionship for every fascination. Exploit them!
You may notice here that I’m not really talking about dating. I truly believe that the best way to improve your dating life is to make your social life more challenging and abundant. That often gets misconstrued as partying and late nights, but it doesn’t have to mean that. What it really means is intentionally applying filters to the ways you spend the bulk of your time, to make each day more conducive to meeting new + like minded people. Going to the same sleepy bar or the same dinner parties with your 3 closest friends might not cut it. Nothing wrong with these things, but if they make up the vast majority of your social life, and the dating apps aren’t working for you… well then we might have a problem. If you feel seen by this article, let me admit that I feel seen by writing it. I struggle with the exact same problem, and have slowly been pushing my way through by casting a wider net IRL. This has resulted in 2025 having some of my best dates, ever.
Let’s change it up together.
- Anonymous contributor from the Cheers community
♥ ♡❦