8 min read

Something’s been eating me. Ever since I started writing again, there’s been one topic that I’ve always wanted to write about, but felt that it was untouchable: dating.

It is an uncomfortable and risky topic for me to dig into, but I’m going to do it. There will be no anecdotes, there will be no “subtweets” and there will be no names named. It doesn’t matter. But let’s sit in these uncomfortable waters together.

I stand before you as an exceptionally single, heterosexual, young adult male. I have no problem with being single, but I go on a fair number of dates (I like to refer to them as “tries” as Louis C.K. does). In general, dates seem to break down about like this:


It’s like a sales pipeline

The good news is, I can count on one hand the number of dates where I didn’t have fun. It’s always fun and a good use of my time, but it’s just generally pretty apparent if we clicked, could maybe click, or just aren’t feeling it.

This won’t come as much of a surprise if you know me at all, but I love Facebook. Facebook is a wonderful tool for:

  • Staying closely connected to a ton of friends (I would argue Facebook allows me to beat Dunbar’s Number)
  • Getting news and information that is relevant and hyper targeted to me by bubbling it up from my curated group of friends and pages
  • Sharing my own ideas and opinions
  • Crowdsourcing ideas, opinions, and information on almost any topic in a very short period of time

I crowdsource so frequently on Facebook that it’s become almost as useful as Google to me for getting opinions and information. Recently, I asked for movie suggestions and received over 100 suggestions in a matter of hours.

But Facebook isn’t great at meeting new people, despite how incredibly creepy and accurate its “People You May Know” feature is. Somehow, it’s still pretty taboo and aggressive to “friend” someone you’ve never even met, let alone have become friends with. Just last week I accidentally stubby-thumbed my way into adding someone I’ve never met, and was so embarrassed I sent this stranger an apology message.

But you know what I’d love to do? I would love to crowdsource blind dates from my network.

Think about it: who knows me better than my friends? They know me better than I know myself sometimes. My friends may know truths about my personality that I haven’t admitted (or don’t want to admit) to myself, but are, nonetheless, still true.

But I can’t crowdsource dates or even coffee meetings with people via Facebook. Why not? Well, good question. I think it’s a perceived barrier, but it feels taboo and uncomfortable. Here are just a few thoughts my inner censor has had when thinking about crowdsourcing dates:

  • Wow, that’s going to come off as desperate.
  • What if no one has any suggestions? That’s going to look REAL sad.
  • Those girls you’ve gone on dates with are going to have a FIELD DAY with this one.
  • This is going to get ugly. What if your friends start tagging people as a joke?
  • This is going to get ugly. What if you get genuine suggestions of people you’re not attracted to? Are you going to just say no?
  • What if those genuine suggestions you pre-screen and say no to were tagged? Dick.
  • What if the recommendations you’re interested in aren’t interested? Can you handle that?
  • Would people even take this seriously? 
  • Even if my friends took this seriously, what if they made TOO many suggestions? I don’t have time for that.
  • You shouldn’t admit publicly how many dates you go on.
  • This is going to deter future women from going on dates with you.

It’s incredible to me how taboo this is. Dating is a HUGE part of young adult life with entire publications dedicated to it or having a dating section. Lust, loneliness, biological clocks, boredom, whatever your reason for being at the party.

It’s a large part of the conversations I have with friends day-to-day or week-to-week. Judging from my own morning pages, I would say that my waking thoughts are loosely divided like this:


But in a public forum, these thoughts and conversations just don’t exist. Not unless your name is tied to it as a byline in a publication.

So instead, we flock to fairly anonymous forms of meeting people. Forms where we get the essence of people distilled into a maximum of 6 photos and 500 characters and we judge them on it.


Putting my best foot forward?

We A/B test our best photos, our best bios, our best pickup lines, and then bemoan the results. I make faster decisions on peoples’ faces than I make on what to wear to the gym. And we spend so much time doing it.

“Is this Tinder, or which digital pimp?” – friend, on how I set up a date

And the best signal that someone on one of these platforms may deserve deeper consideration? The “mutual friends” feature. I place more stock in that than anything else, which leads me back to my original point: Why can’t I crowdsource dates?

But this is just the tip of the iceberg.

No matter the method of meeting someone, dating as a young professional in this landscape is rough potatoes.

It was so easy to swipe to the point of meeting someone in person that I find myself having the same impatience after that initial meeting. Sometimes dates turn into interviews (maybe even interrogations). How quickly can I learn enough about this person to determine if there is any type of future here?

It’s like both parties have this standardized internal flowchart. Question/test; if yes > next question. If no > next question. If the path flows to a certain point, terminate interest.

And if the path leads to a favorable endpoint from a meeting? This is where it gets really tricky. Now I have to portray genuine interest without appearing overenthusiastic, clingy, or weird. But don’t show too much interest – that will shift the balance of power. Women don’t like when you make it too easy, you have to maintain some mystery.

Do you kiss on the first date? What are the implications of that? What if you don’t kiss, how do you show genuine interest?

OK that went pretty well, how and when do I follow up? Do I call, do I text? What’s the proper amount of time to elapse? What do I say? Better make sure that I still maintain this balance of interested but not overenthusiastic, clingy, or weird. Can’t shift that balance of power. Women don’t like when you make it too easy, you have to maintain some mystery.

And all the while, women are (probably) having the same internal struggle. Who knows, maybe it’s even more complex. Now we are just playing chess and shadowing each others’ moves. No progress being made here.

She must not be interested. “He must not be interested.” 

On to the next wave of swipes.

Oh this is great, we’ve both agreed that we hate the games involved with dating. Great, now I can be myself, be honest, and admit that I’m feeling a real connection here. Oops, we thought we didn’t want games but now I just tipped the balance of power because I’m appearing overenthusiastic.

“Mystery gone, interest lost.”

On to the next wave of swipes.

Oh this is really great actually. No real games here, I feel a real connection. This is going well, we’ve spent time together each of the last several weeks and this is really starting to click. But man, work is busy this week. I have meetings or events every evening next week, and I’ll be out of town this weekend.

Weeks pass by…communication become infrequent…

The immediacy of intimacy we’ve come to expect from college and early professional schedules has ingrained a subconscious expectation of how quickly things can and should move when things are going well.

She must not be interested. “He must not be interested.”

On to the next wave of swipes.

This is not about complaining, and this is not me pointing a finger at anyone else. I’ve allowed myself to become conditioned to weird “red flags” and to have certain expectations that I probably should not have.

Hell, sometimes there are no red flags at all. Sometimes I invent red flags because vulnerability and intimacy threatens my happiness and productivity. I self-sabotage or withdraw.

Maybe you have too.

I share all of this because I get bored with the convention of what thoughts should be shared publicly. I get bored censoring thoughts and experiences. I get bored reading sterile and unoriginal content on social media when I know there are experiences worth sharing, conversations worth having, and better dating realities. I don’t even buy into the concept of one perfect soulmate – I think there are probably hundreds if not thousands of “the one” out there.

I just wonder how many I’ve swiped left.