Dating Advice for the Socially Awkward

Lemme put this right on front street: I'm terrible at dating. Think Steve Carrell in 40 Year Old Virgin. That's how bad I am at it. And yet I've been involved in a relationship of some sort pretty much my entire adult life. Despite my incompetence, I seem to be doing something right.

Yeah

I'm not an expert at dating. Not by a long shot. But the last time I was single I started doing a lot of reading about various components of interpersonal docking procedures, because I figured there had to be some trick to it, and I was determined to understand what that was. I haven't been single for some time, but the idea still fascinates me, so I haven't stopped that reading.

What I present here is the current synthesis of the knowledge I've picked up about it. I hope I'll never need to use this myself, but there's no reason others couldn't benefit from my research.

If you're good at dating, or you've got an approach that works for you, you don't need my advice. Just keep right on doing what you're doing. If you're having a hard time of it, consider trying some of the things I suggest.

Step 1: Know What You're Looking For

This is hard. A lot harder than you may expect. You probably have a shopping list of traits in your head that describe your ideal partner, right? Here's the problem: that list is almost certainly wrong.

Think about it like this: if you've ever used a service like Audible, Amazon Kindle or Netflix (or equivalents), odds are you have a lengthy wishlist of items you "plan" to buy, because they're the sorts of things you like, right? But if you like them so much, why are they still in your wishlist? Because when it's time to actually buy stuff, you buy other things.

As humans we suck at knowing exactly what it is we like. We have an imaginary list of things that we may be interested in, or wish we were interested in. But that's not the list that actually determines our purchasing behaviour. The actual list is hidden from us, down deep in the recesses of our reptile brains,

Amazon and Netflix know this, so they don't bother suggesting new purchases to you based on what you say you like. They look at what you actually buy, compare that to other users who bought the same things, and show you recommendations based on what they bought. And that seems to work pretty well.

Alas, we're no more or less skilled at picking potential mates. We have an idea in our minds of the sort of partner we ought to have, and search for that. Meanwhile we overlook plenty of opportunities with people we would actually like.

Online dating sites are aware of this, and are presumably working on incorporating it into their matching algorithms, But until they they get it right, the most we can do is to be brutally honest about what we actually want in a partner... not just what we think we ought to want.

And the easiest way to start that is to look at your dating history and do a comparison of your previous partners. Ask yourself questions, and answer as honestly as you can. Things like:

1. What first attracted you to the person?
2. What annoyed you most about them?
3. What traits (if any) do all or most of your partners share?
4. What did I find most rewarding about our time together?
5. What did I miss most after we broke up?
6. And so on...

I warn you, this can be difficult emotionally. When I went through this, I had to admit to myself that my answer to #1 for most of my previous partners was "She was nice to me.". Ouch. Take your time and work it through. It's worth it.

Don't be afraid to be superficial or prejudicial. Nobody's watching, and nobody's judging. If you don't like tall guys, that's cool. If blondes do it for you, that's cool too. You're not trying to impress anyone, you're trying to get to know yourself better. If you don't like what you find, make a note to work through it later. This is about knowing yourself, not fixing yourself.

When I was doing this a couple of years ago, I gave into my geeky urges and created a spreadsheet with 34 different listed criteria, each with a comparative weighting, and I rated all my previous partners against each other to derive an overall compatibility score out of 100. I have no idea if it was any good, but the results certainly reflected how I felt about them at the time, so I guess there was some merit to it.

In fact, since I already had the matrix in place, I created an online questionnaire and invited my friends to fill it in... mostly so I could calibrate it better. I wouldn't recommend that to you, necessarily, but I will say that one of my friends who filled out the questionnaire got an impossibly high score. And, well, we've been together for close to two years now. So there's that.

Step 2: Marketing

A lot of people are uncomfortable, particularly when it comes to online dating, with "selling themselves". Not only are we culturally discouraged from singing our own praises lest we sound arrogant, but many people suffer with self-confidence issues. And let's face it: if you're looking for dating advice from me, odds are you're one of those people. Amirite?

But that's okay. You don't need to be a master salesperson or Don Draper to be the director of your own marketing campaign, There are some basic steps you can follow that will get you off to a good start.

1. Have a good, recent profile photo. I cannot overstate how important this is. Not only should it go without saying that you must have a profile photo, but you want to ensure that you have the best photo possible.
   
   Humans are visually-driven. It's not worth denying it. We evaluate prospective dates first (but not only) based on their appearance. It's just true. If your profile has no photo, or has a photo of something other than you (your child, favourite cartoon character, a pretty flower or whatever) you won't get any good prospects. You'll get messages, especially if you're female, but they'll only be from random dudes trawling the sites... not from anyone worth talking to. Photo = essential.
   
   Even if you don't think you're very attractive. If anything that makes it even more important that you have a photo up there. While it's true that there are some global norms of attractiveness among humans, that's highly variable. Even if you look funny, odds are there's someone out there who thinks your look is cool, quirky or cute. You'll never find that person if they can't see your face.
   
   Not only must there be a photo, but it must be a clear one. Get one taken professionally, if you can. By an actual professional, if possible. Your friend with an expensive camera who photographs her friends' pets on weekends might be able to do a good enough job, but try to get the best you can afford. You want the photo to depict you clearly and honestly, but should also be as flattering as possible. Good lighting, composition, make-up (if necessary) and wardrobe make all the difference. Most people don't look good in bathroom-mirror selfies. Go legit for this one.
   
   Not only must it be good, but it must be recent. Less than a year old, preferably. There's no point denying it: we all change the way we look as we get older. We put on or lose weight. We change hairstyles and hair colour. We make different fashion choices. Our skin changes hue and texture. Despite what you imagine you see in the mirror, I promise you don't look like you did three years ago. If you set up a date to meet someone who's there to meet the 2011 version of you, and they see the 2014 version of you instead (even if you think the 2014 version is more attractive), they'll be disappointed, because they won't be getting what they signed on for. Putting up an outdated (or heaven forbid, heavily photoshopped) photo is dishonest. Don't do it.
   
   Have a few other photos too, preferably in a variety of settings, doing things you enjoy.

   

   No duckface selfies

2. Give yourself a good blurb. Most dating sites require you to say something about yourself in your own words. Be honest and direct, but try to keep it positive and light. For example:
   
   Instead of saying "I've been single for 3 years now and I desperately need to get laid."
   Try "I've spent some time enjoying life on my own, getting to know myself. But now I feel ready to share my life with someone special."
   
   Good, eh?
   
   Don't hide important things about yourself. Put them right out there. Especially if it's something unusual. If you collect snakes, can't go a week without watching an old episode of Magnum PI or only ever eat fruit that died of natural causes, you need to put that stuff out upfront. Those could be nasty surprises for someone who wasn't expecting them, or they could be the exact things a potential partner is looking for.
3. Don't limit yourself. If you're unaccustomed to the online dating thing, it may be daunting to sign up for even one site. But in for a penny, in for a pound. If you're going for one, may as well go for as many as you can: DatingBuzz, OKCupid, eHarmony, Match.com... don't stop until you've got a hook in as many ponds as you can handle.
   
   There's no reason to limit yourself just to dating sites either. Social media sites like Google+, Facebook, Twitter, Pinterest, Instagram and Meetup are also good platforms to get yourself out there. For all you know, your next romantic partner has been your Facebook friend since 2009, but they just didn't know you were available. There's no need to go overboard and spam your friends list with flirty messages, but you can incorporate some elements from your dating profiles into your ordinary social media profiles without it being weird.

Step 3: Get out of the house

Online dating is cool and all, but as popular as it is these days, you still have a much higher chance of meeting a good match when you're offline.

Now, I've been there: when you're single, there's a strong temptation to go to places where single people go: night clubs, pubs, birthday parties of loose acquaintances... but that's a tactical error. If you're the sort of person who ordinarily goes to a pub often, then go to a pub. Because the people you'll meet there are people like you: people who go to pubs. 

But if you're not normally a pub-goer, going to a pub to meet people doesn't make a lot of sense. Do you really want to meet someone who wants to do something regularly that you don't like doing?

Instead, go to the places you normally go. If you don't normally go to places, use Google to find out where people like you go. Are you new to Joburg? Join the Joburg Expats Meetup. Are you an atheist? Find out when the next atheist picnic is. Are you a geek? Come to DeeTwenty!

It seems obvious when you think about it, but it doesn't necessarily occur to people: if you want to be in a relationship with someone who shares your interests, hobbies, world-view or values, seek out people that you share those things with, and see who you meet there. You're more likely to meet the right person there than you are in places where other people go.

Step 4: Be patient

This isn't an aggressive sales technique. Nobody's screaming in your ear to make 20 calls by end of business. Relax and take your time. Be comfortable with the idea that finding a good match can be a slow process.

Desperation is counterproductive in these situations. People can pick up on it, and it makes you seem less desirable. 

Instead, focus on enjoying the last days/weeks/months you have of being single. Maybe do some of the things you're unlikely to do when you're not single anymore, like spend a night on the roof with your telescope, take your parents on a weekend away, or go with your buddies to a strip joint. Try to enjoy the single life, and you won't mind as much that it takes a while to happen.

Odds are you'll meet a few people along the way who aren't a good fit. I wish I could give you comprehensive advice on how to deal with that, but the best I can do is: be kind, be honest and be clear. And bear in mind that even if the guy or girl you're with now seems unfathomably awesome, if he or she doesn't feel the same way about you, there are almost certainly are others out there as unfathomably awesome as they are, if not better.

So yeah, like I said, I'm no expert. This is based on stuff I've read (I've linked to my sources when I could find/remember them), and it all makes sense to me. But dating is messy business, and your mileage may vary. I hope you get something useful out of all this.

Oh, and I'm serious about the profile photo. Muey importante.