Dating has always been an odd experience. There are rules, but nobody knows them. There are special codes, but nobody has a cipher. Yet, somehow, unless you're in your 20s, things are weirder than they've ever been.


I've always felt dating was a weird experience in general, but somehow, coming back to it in the last few years feels different. I was married for several years in my late 20s, so I missed out on the earlier days of online dating sites. It was also a much more carefree time, when if you liked someone, that was enough. But now that I'm in my 30s, the rules and expectations are completely different—making it a lot harder to get back in the game.

It's Hard to Deal with the Amount of Options Online Dating Has Brought


Right now, you have billions of other human beings at your fingertips through a variety of channels. As always, you can hit up bars, clubs, and shows. You can venture off to parties and barbecues. You can also go online and have access to loads of single people in your area. It's a far cry from even high school, when your dating pool was largely pretty much your friends and their friends.

Online dating gives you more options than ever. Not just in people, but in sources. Dating sites like OkCupid, Tinder, Match, eHarmony, and Plenty of Fish all give you access to other single people in a matter of seconds (I'm too old for Tinder though). From there, you can sort through humans with enough filters to make Amazon jealous, then randomly spit out a message to them that ends up coming across the exact same as the "do you like me?" notes you passed in middle school.

These unlimited options are great at first, but just like any decision, the sheer amount of choice ends up weighing on you. You nit pick. You wonder if their affection for Vampire Weekend would end up getting annoying. You question their odd use of Billy Madison quotes. You're paralyzed by both an abundance of choice and a fear that something better is out there because "good enough" isn't good enough. In the past, I met people through a larger community and that was enough. Now that the community is even bigger, it's hard to make choices about who to even talk to, let alone see in person.

Plus, with online dating, everyone's so preoccupied with how good you are "on paper", which means very little. An algorithm can predict whether you'll get along well enough to hold a conversation, but it can't predict whether you'll like each other, so people get frustrated. Those match percentages and pre-date emails create an expectation that's often impossible to live up to. That algorithm ensures you won't want to slit each other's throats (usually), but you can't guarantee that shared political beliefs or a preference about your favorite cereal will create a spark.


I found online dating hard to keep up with in general. I was disappointed when a well-placed pun fell on deaf ears and generally annoyed by the flakiness of people online. I had a handful of great dates and met some nice people, but I wasted too much of my day to get there. It's basically a full-time job, so make sure you're invested in the whole idea, and don't overdo it. Delete the apps from your phone, deactivate your account now and again, and give the whole thing a break if it's not clicking for you. I met plenty of great people and found some cool bars, but it was an empty experience.

The Deal Breakers Have Changed, and They're Much Bigger Deals


When you're in your 20s, deal breakers tend to be pretty superficial. It might boil down to what music they like, a dumb haircut, or a subtly annoying nervous tick. If you’re smart, you learn to ignore these things and be more open-minded.

Once you hit your 30s, these things change. Some deal breakers are just as superficial, but people have added much heavier ones, too. In my experience, first or second date conversations already started hitting into the hard questions of children, career, home ownership, and marriage. The older you get, the less time you have, and the less time you feel like wasting on someone who doesn't have the same goals as you. Still, I was pretty surprised at how quickly these conversations came about. It's not good or bad, but if you haven't come to conclusions about these types of things, do it before you venture out into the dating scene.


Of course, the superficial deal breakers are still there, hiding the deeper ones beneath the surface. I polled random people over the last few weeks, and found pretty low expectations in general. Several people of both genders mentioned deal breakers like, "they can't be a slob," "they need a fulfilling career or at least a hobby they enjoy," or "they can't live in a house with more than one other roommate."

But the most surprising deal breaker? The one that nearly every person I talked with mentioned? "Must have a bed frame." It turns out we're still not asking that much of our potential partners...until the second date, when the conversation almost always turned to kids and marriage.


The "Game" Is Different, and Bluntness Is King


Want to stop seeing someone? Want to ask someone out? Just say it (without being a creep, of course). When you're in your 20s, it's all about the game, but the game changes the second you hit 30. Nobody wants to waste time beating around the bush, so if you want to ask someone out, just do it. If you want to stop seeing someone, tell them right away.

Likewise, the old "three day" or "five day" or whatever-day rule of asking someone out again is out the window at this age. If you enjoy someone's company, ask them out again whenever you want. Chances are, the two of you will split hairs over scheduling conflicts for a while before you settle on a date anyway.


For that same reason, things seem to move a lot faster after your 20s. Gone are the days of months and months before that dreaded exclusivity conversation pops up. In my experience, it happens a lot sooner if you're seeing someone frequently, so if you're not prepared for it, back away early.

So What Do You Do?


Dating is weird no matter how (or when) you approach it. But if you're coming back to it in after some time off, I have a few suggestions based on my experiences:


None of this stuff is good or bad, but it is awfully different from what I remember the last time I went through the whole dating thing. Whether you're returning to the dating game after being sidelined for a while or you're just rolling along solo into middle age, prepare yourself for some confusing times. There's certainly an adjustment period, so don't be surprised if you fall flat on your face a few times before you get the hang of things.

Photos by Julia Tim , bixentro , Brett Lider , Cory Doctorow .