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Getting Their Backstory! The fun way of getting to know someone you just met online.


It’s been a week since starting my profile on Plenty of Fish. I decided that – since my karaoke night didn’t quite go as planned – I’d probably be best off practicing on this new fandangled gizmo called the internet. I’ve had very minor success in getting the attention of the fairer sex, but there have been a few bites from those I’ve sent messages to.

Mine was a cliché – no bells and whistles – type of profile. Containing several non-thought-out photos I managed to scrape up on Facebook, and descriptions of random things I like. The standard where I work, food I like, blah blah blah boring stuff. So, it goes without saying, that it was a little tough getting girls to notice me.

But one night – while playing Dragon Age surrounded by bags of Doritos and empty pop bottles – I got a ping!

“Hi there. I see you have tattoos. How many do you have?” it said.

Excitedly, I wipe cheesy fingers off on my shirt and proceed to respond with “I only have one, but plan to get more in the future. What about you?”.

“Oh nice. I have three” She replied. “How’s your night going?”

“Wow three? I’m jealous” I felt I was being cheeky, but, it was just lame. “Night’s been good. Chilling. Not much happening”.

“Oh. Well that’s fun. Ok have a good night”

“Thanks! You too..”

That was that. Nothing came of anything afterwards. I just went back to playing videogames wondering what I needed to do to get a real conversation going.

I’m sorry. That was a lot less climactic as my usual story telling interlude. However, I felt it necessary to reflect on just how lame I was in that very moment, and that it was the most relatable to your experiences with online dating. I’ve been there, done that, and designed the t-shirt.

This leads us into what the heck do you do when you finally get that attention you’ve craved?

The answer – my friends – is what we all love as geeks. Something born and bred into our DNA it encompasses the very core of what we’re all about. It comes in various forms; Board, card, drinking, table top, and the ever so popular video.

If you answered games you’d be right!

Yaaaayyy games! Well.. Game. There are – in fact – a ton of games playable via text that you can plug into your repertoire as you get used to this method. I’ll make a separate post listing all of them a little later, but for now I’m going to explain the rules of one specific game that worked well for me while I was getting used to this dating thing. I call it…

20 Questions!


I know I know, you all know the popular car game – with the same name – everyone everywhere ever has played since the beginning of time. Yet no, this is not a texting version of the “trying to guess whether I’m thinking of a person place or thing” while driving through the Grand Canyon with mom and dad.

The rules of this game are simple. Player 1 (you) and player 2 (him/her), take turns asking each other questions. The queries start off simple. For example, “What is your favorite colour?”. As each player has a turn, they ramp up the personal info a little. Getting more and more intimate as the game progresses.

An example of it can look like:

You: What’s your favorite colour?

Her: Blue… You?

You: Blue as well! Look at that, something in common already! Your turn.

Her: Oh.. Umm… What music do you listen to?

You: I like pretty much anything that has good lyrics and tone. My playlist contains anything from Adele to Metallica, Eminem to Queen.

Her: OMG.. I love Eminem! Ok.. Your turn?

You: Well now, yet another thing in common! This is starting to get creepy. You’re not Facebook stalking me are you? 😉 Have you ever had a silly nick name?

Her: Maaaaaybe.. But you’ll never know lol. Ugh, yes.. I used to be called monkey feet in highschool because I was able to pick up anything with my toes 😐 Don’t judge.

You: Ha ha.. Monkey feet! That’s adorable. I’ll have to keep that in the ol’ memory banks for future use. I do believe it’s your turn.

Her: Future use eh? 😉 What is your favorite thing to do during your down time?

You: Lol. I don’t assume anything. I just says it how I sees it, and I definitely sees a date in the near future. I love to go out for karaoke on my nights off. Sing my face off, make an ass out of my self. All my friends point and laugh. Its fun!

Her: Oh you DO do you? Are psychic or something? OMG you sing?! That’s kinda hot.

You: I don’t know, you tell me. You’re the one on my Facebook Page 😛 I do sing. Doesn’t mean I CAN sing lol. Perhaps I’ll let you be the judge of that someday. I do believe it’s my turn. What’s the most romantic thing done for you?

Her: Maybe you can show me during that first date you mentioned 😉 Ohhh.. I don’t know. Someone bought me flowers once….

And so on….

The game is called “20 Questions”, but there is no limit to how long you play. You can go for 30 or just 10. It’s up to you really. The number is moot at this point.

Now let’s discuss 3 things that you are doing while playing this game.


It Makes You Fun.


People love games! Everybody who’s anybody loves to play. It’s just a thing that’s embedded into our systems from childhood. I know this seems like it’s just a normal conversation as there’s no real winner or loser. But! Giving it that “game label” makes it seem like it’s something completely out of the standard job interview like “getting to know you” scheme. Play it up as though each new series of questions are new levels and get harder.

It Builds Trust.

Starting off with the smaller questions and building your way up to get her (or him) describing more intimate details shows that they are already starting to trust you. It builds rapport. People are more willing to hang out with someone they trust.

Remember. With her trust in your pocket, it is easy to get her feeling romantically towards you.


You Learn Everything You Need to Know to Build a Perfect First Date


When playing this game, you can itemize a list based on your findings. Say you find out her favorite colour is blue, her favorite flowers are lilies, she loves rollercoaster rides, her favorite food is Korean BBQ, and that she loves to peruse the mall.

Now you can design a day where you pick her up holding blue lilies, take her to your favorite amusement park or the fair, hit up that new Korean joint near the mall for dinner, and then walk it off while shopping.



There you have it folks. A simple but fun way to get to know someone you met online.

Something to note. Try to read the room – so to speak. If the conversation isn’t going towards a sexual theme, don’t go spewing forth questions about their favorite position. I know it’s extremely tempting to go that route. In the same regard, if it does – cause sometimes it will – start going that way, by all means explore it!


Kurtis Kehoe – he’s got 20 questions and he’s not afraid to ask them


Ladies, sometimes you should grab the bull by the horns and make the first move

Even after playing 20 questions, sometimes you’ll get rejected. Here’s how to move on

Get direct access to Kurtis and the rest of our coaches in the Facebook group