3 Things I’ve Learned About Dating In 2014 (After A Decade Of Being In A Relationship)

I started dating my ex-wife when I was 21 and married her at 23. Now 30 and divorced, I’ve recently begun my foray back into the dating world. A lot has changed since I last dated, and having spent my 20s in a committed relationship, I missed both the prime single years and the development of the dating culture. Jumping into the dating pool right now feels more like being physically thrown into a freezing pond.

Maybe it’s because of how long I’ve been out of the game, or maybe it’s because I’m simply not very hip, but one thing is certain: dating in 2014 is strange territory for me.

With that said, here are some anecdotal lessons I’ve learned in the short time I’ve been playing the dating game…


1. Showing Overt Interest is Unattractive

The art of successful dating in 2014 involves showing just enough interest in another person without showing too much. Apparently at some point in the last ten years, paying close attention to a woman has become uncool. I’ve asked several friends how to approach and talk to women. The advice I’ve gotten repeatedly from multiple sources? Act aloof.

Wait, wait, wait. Hold on. You’re telling me the most effective way to attract a woman I like is to…act like I don’t care?

My theory is that in 2014 America, everyone is sooooo busy and even if they’re not, there’s social pressure to appear to participate in as many interesting activities as caffeine, Adderall, and four hours of sleep will allow. Thus, when I make a genuine effort to pay close attention to a woman, I appear to have no life and nothing better to do than sit around waiting for her text response about her favorite 90s boy band (Backstreet Boys, obviously).

Going into this, I had an idealistic notion that adults would date the way adults do everything else. I mean, in my grown-up business job, I don’t ignore emails or phone calls for fear of appearing desperate. If I did, I’d be unemployed. But dating at 30 is remarkably similar to dating at 16. The point of the game is to be the one who cares the least.

Maybe I’m old fashioned, but why is it such a negative thing to be upfront with a woman about liking her? I’m not talking about constantly showering her with compliments or following her around all doe-eyed. I mean engaging in a normal conversation between two people who are not afraid to admit they’re attracted to each other. What is this, the 6th grade? I like her, BUT DON’T TELL ANYONE!

The ultimate death sentence seems to be asking a woman on an actual date. No, she doesn’t want to carve out a time specifically for me. No, she’s not interested in altering in any way the plans she has for watching Bravo with her roommate or doing nail art or Netflix binging on the couch with her dog. Committing to spend time with me at the expense of ALL THE OTHER IMPORTANT SHIT in her life would most certainly serve as a clear indication that she’s attracted to me. Un. Cool. If she can’t casually “bump into me” at a local bar, it’s not happening.

No, Random Girl From Tinder, I do not believe your life is so busy that you can’t find an hour for lunch some time in the next three weeks. No, I do not buy your story that you’ve felt like a bad doggie mom and need to go home to spend time with your precious Sophie instead of meeting me for a happy hour drink after work. She’s a dog. She’ll survive just fine for another hour and a half without you. Sophie doesn’t buy your bullshit story either, by the way.

2. Social Media Image is THE Image

Facebook became available to students at my college when I was a senior, and at the time it was pretty useless. There were no status updates, no picture galleries, and not much in the way of a messaging service. It wasn’t a time-suck like it is today, because there wasn’t much to it.

Now, not only are there dozens of ways to craft an image on Facebook, but there are also dozens of other social platforms and they’re all REQUIRED. It’s no longer enough to be attractive in person; Tinder, Snapchat, Facebook, Twitter, Instagram, et al. combine to project a virtual image. And since phone calls are not an option (see #3 below), the only way to attract someone is by mastering the art of the virtual image.

I’m generally not a very photogenic person. I think I project a higher level of attractiveness face-to-face than via social media. Also, I don’t really like taking a ton of photos, especially of myself. When I go to a good concert, I want to focus on enjoying the music and the friends I’m with. I give zero shits about passing my phone off to a stranger so my buddies and I can document seeing Phantogram for the 37th time.

But in the dating world, if my Instagram and Facebook feeds aren’t overloaded with “X-Pro II”-laden pictures of beautiful people doing interesting things every single day, I appear like, totally boring. By the way, cute pictures of my cute kid doing cute stuff don’t qualify. I know, I’ve tried that.

I mean, do you people hire professional photographers to follow you around telling you where to stand, how to tilt your head just right, and in which hand to hold your noticeably expensive cocktail?

3. Phone Conversation is a Lost Art

I was in junior high and high school in the 90s, college in the early 00s. Text messages weren’t a thing, and chatting online was still only for hyper-nerdy geeks (I can neither confirm nor deny that I was one). Back then, when I liked a girl, I got her (parents’) number and called her in the evening. Conversations often lasted hours, and somehow we never found ourselves at a loss for things to say. Being a good phone conversationalist was a necessary art to master.

Today if I get a woman’s phone number, it’s the last time I will ever hear her voice.

I met a woman at a bar a few weeks ago. I caught her eye and we danced together for the last few songs of the night. When the lights came on at closing time, I asked for her number and she obliged. The next day I struck up a text conversation. I asked about music and movies she likes, places she had traveled, etc. Each interchange was punctuated by at least a ten minute pause on her part, then a one- or two-line response. The conversation lasted about 48 hours, then she quit responding altogether.

Damned if I know what I’m doing. There’s some kind of black magic alchemy involved in reading a text from a woman, waiting long enough (but not too long) to reply, crafting a witty response that makes her smile (but doesn’t sound like I’m trying too hard), then sending it through the best medium. Do I reply to the text? Do I send it via Snapchat art? Test her cryptography skills with a string of eight Emojicons?? HOW DO I MAKE YOU LIKE ME???

There’s no way in hell she would have agreed to a phone call. That would have required her to pay attention for a solid half hour. It would have brought her into direct contact with someone who was actually interested in talking to and learning about her. It would have eliminated her ability to act aloof and think about every response for 20 fucking minutes.

Also no way she would have agreed to meet and spend time together before she vetted me through her texting gauntlet. I’ve learned this much: good luck earning a coffee or lunch date if you can’t impress her via text. Is this not the most ludicrous thing anyone has ever heard? Your strategy for finding someone you’ll enjoy spending significant time with is to…spend zero time with him and never hear his voice before you stop responding in less than a week?

By the way, ladies, don’t do that. We’re all adults here. I’m a big boy and I can handle rejection, especially from some rando I matched with on Tinder two days ago. If my texting style isn’t your thing (because we’ve obviously never met face-to-face), then say, “Thanks, but no thanks.” Give me a good excuse. Or a bad excuse. Or tell me to fuck off. But, please, for the love of God, do not just randomly stop responding. That shit is fucking infuriating. I NEED TO KNOW WHAT YOUR HIGH SCHOOL MASCOT WAS.


I’m learning that successful participation in the dating scene today requires putting exorbitant effort into looking like I just don’t care. A person must appear witty, funny, and attractive 100% of the time. But, you know, without letting it seem like he’s actually trying. Christ, I feel tired just thinking about it. People are insane.

It also involves zero human interaction until every inch of your life has been laid bare through Internet stalking and three weeks of Vetting By Text Message. Successfully meeting a woman for a date is like being hired as a government contractor. Before she’ll consider you as a lunch candidate, she needs a security screening, two personal references, a credit check, and your last three addresses (Why DID you live in that apartment for only three months? Hmmmmmmmm?).

I’d like to think that if I simply act like a grown-up, others would be compelled to do the same, but the truth is, I’m just as addicted as everyone else. The dating game has its major flaws, but that sure as hell doesn’t keep us all from wasting hours swiping on Tinder or stressing about how to reply to a text. The game often sucks, but I can’t seem to quit playing.

So I continue asking women to tell me their favorite Disney movies, local bars, and celebrity crushes. And only after I’ve waited at least ten minutes. But you know, not too long.

Speaking of long waits, if Homegirl from the bar is reading this: I’m still waiting for a response about your favorite ice cream flavor. TC mark

featured image – New Girl

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  • http://datingamiss.wordpress.com datingamiss

    Hang in there. Some if us females find dating just as frustrating.

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