Ultimate Wingman

My friend Troy has been single a long time. Like…a really, REALLY LONNNNNNNGGG time.

So, me being me – I had to step in and help the guy.

I appointed myself “ultimate wingman” and set up a dating profile for Troy on “Plenty of Fish“. It’s a bit scary how easy it is to be ‘someone else’. The internet gives us access to people’s photos, their birth dates, their interests…scary.

Lucky for me, I’m an actual friend…so being Troy wasn’t too hard. I know he loves kitesurfing and music and is an amazing guitarist. I had access to his pics thanks to Instagram and it took me all of 10 minutes to set his profile up.

I was annoyed because I had to PAY for a month’s subscription. Grr. It’s okay, Troy. I got you, man. I put my card deets in. It will be worth it at your wedding, bro.

I chose ‘looking for women’ and made the dating age between 31-40 because Troy’s around 43…I think? I know he seeks out 20-somethings and wonders why it doesn’t lead anywhere. SIGH. It’s because you’re too old, boy. I felt like I was approaching the online dating game with a lot more common sense. My age range opened up the field a lot for old Troy boy. All good.

Plenty of Fish brought up basically a ‘hot or not’ page where a girl’s picture pops up on screen and you swipe left “hell no” or right “yes” on it.

It’s been 10 years since I have seen internet dating and this is legit scary. It’s so…judgy!

Here’s how I picked girls for my friend:

  • anyone that looked really old – OUT
  • anyone showing their boobs – OUT
  • anyone with filters on (I’m a girl, I’m not fooled by that nonsense!) – OUT
  • anyone with alcohol featured in their pic – OUT
  • anyone in a group photo (I mean come on girls, wtf?) without something pointing out which girl they were (Imma assume it’s whoever looked OLD AF and horrible in the group) – OUT. IMMEDIATELY.

The girls I did pic:

  • smiled in their photos. I like that for Troy
  • dressed modestly/stylishly ^^ as above
  • showed a few photos where you could see their full bodies. I like the honesty in that. Yass girl, OWN it.
  • showed themselves doing something – playing sports, hiking, on the beach, out with friends…I like to see that Troy gets to date someone who does stuff. Very good.

Then, I had to message them.

This is weird for me as a girl because I wait for the guy to message me. I like to be chased. I think we all do, right? But I had to be the guy in this situation so I had to message first. The pressure!!! It makes me appreciate guys more – it’s a lot.

I mostly messaged “Hey, how are you?” which I think is a great start.

I got a pop-up message back instantly from a lot of girls, saying “Chloe/Emma etc does not respond to any messages shorter than 10 words – please write a longer message”


The cheek of it.

So then I had to ask an interesting question. I had to be witty and charming instead of just being able to say “hello”!!! WHY IS ONLINE DATING SO BLOODY HARD???

So I tried ‘ice breakers’ with lots of girls, eg;

“if you could go anywhere in the world, where would you go and why?”

“What would your perfect date be?”

“What makes you happiest – why?”

and wait for a response.

And wait more.

And wait. WAIT. WAIT.

Girls are RIDICULOUS, honestly. Why didn’t anyone message back?

While I waited, I headed back to “Troy’s” home page to look through…and I’m not even joking here…hundreds of potential girls for him. It was hard work. I got the unique opportunity to see online dating from a guy’s point of view and it’s not fun. It’s hard work, no one messages back and you have to go ALL OUT from the beginning just to get a foot in the door.

So I messaged every potential girl for Troy. I made him witty, kind, funny and sweet. Unfortunately for me, I couldn’t take myself 100% out of the messages so “Troy” got very excited at times and there were a lot of “OMG!!!” comments. Girls didn’t seem to pick up on it.

Then the messages started coming in.

Troy lives in Melbourne, so I set his dating perameters around Melbourne. I don’t know anything about that city, I live in Perth. I also live 3 hours behind Troy in Perth so when I was busiest at work, it was dinner time in Melbourne and all the girls wanted to talk to Troy. GREAT.

“Can you go onto video chat?” girls messaged.

I can’t. Firstly because I’m not Troy so you’ll get the shock of your life…and secondly because I’m at work and can’t just ‘chat’ to you right now.

So I tried as nicely as I could to put these girls off. I used very good excuses “Just popping into a meeting” “just about to give a music tutorial – can we catch up in a bit?”

NONE of the girls accepted my reasons. A lot of them told me off!

GIRLS ARE HARD WORK. They are pushy, demanding and not easily impressed.


Being a boy is hard.

I lost a lot of girls by not being able to video chat with them immediately. Grr.

The girls I did talk to wanted Troy (me) to be interesting, smart, witty and entertaining. By the time I was able to message them back, I was tired from a full day of work and didn’t have the patience for their bollocks. I can’t be impressive at the drop of a hat. Who can? Girls wanted to be chased and entertained. I just wanted to get to know a girl, you know? Nope, they don’t want that. They want to be impressed.

A few girls asked “Melbourne” based questions which I didn’t know how to answer – about clubs, cafes and suburbs. I just tried to deflect by asking them about themselves. I know girls because hey, I am one – and we love to TALK so I kept them talking. Easy.

I wasn’t able to keep this up because work’s been mental and online dating is more like a full time job than my temp assignments were. I had only paid for a month (sorry Troy!) so I had to give up my ultimate wingman adventure.

This is what I learnt for my sisters out there, though:

  • Message a guy back!!! Guys wait so long to hear back. Just send something to him, you’ll make his day
  • Don’t expect too much at the beginning – just let him get to know you. OMG!
  • Not all guys can be interesting and witty. Just talk to the guy! Give him space and time to talk back to you and LISTEN to him when he does. Don’t rush him.
  • If you’re going to post a group photo…and honestly, it boggles my mind why you would do such a thing – then use the edit ap on your pic to point yourself out! And add photos to your profile with JUST YOU in them. Don’t try to trick a dude into talking to you by posting a pic of 6 girls – just be YOU. Who you are is going to be enough.
  • NO MORE FILTERS. Like…omg. We do NOT look that perfect in real life. Post REAL LIFE pictures. For the love of God.
  • Post at least ONE pic of your whole body. If you post just face pics, that’s all good and well..but when you meet in real life and he sees your stomach and ass…it’s all over. You’ll deserve it when he ghosts you the next day…so don’t go there. Just own it, girl. I bet you are gorgeous.

To all the lads, I feel you. I experienced for myself how f**king HARD it is to online date and I salute you. Keep trying. Keep messaging. Don’t give up.

3 responses to “Ultimate Wingman”

  1. This is so interesting, to see online dating from the man’s perspective! I do recognize myself a bit in how women respond. I guess we quickly assume men just want sex, even if they ask something interesting or simply say “hi how are you”. Women should put in some effort too if they’re looking for a partner!

    Liked by 2 people

    1. Omg you’ve made my day commenting on a blog I wrote!!! I squealed in excitement hearing from you!!! Yeah it definitely gave me a new appreciation of guys when I tried to BE one. Online dating is a JUNGLE and my heart goes out to anyone trying to find someone genuine on there. The guy you end up messaging will be so happy just to hear from you. Let me know how you go xx

      Liked by 2 people

  2. Haha us smaller bloggers have to support each other! Glad it made your day 🙂 I did realize that guys are happy when women respond. I wouldn’t have met my boyfriend otherwise! Hope Troy finds someone great too 🙂

    Liked by 2 people

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: