First Date Trouble Shooting for Men | CLiKD, Creative Dating

First Date Trouble Shooting For Men

  • First Date Trouble shooting for Men

    So you signed up for online dating, and now you’ve bagged a first date. Well done my son! Now you have the small matter of organising it, and then not f*****g it up. Easy right? Well, it can be… but we thought it might be helpful to disaster-proof you, just in case! Let’s break down first date trouble shooting for men…


    So you’re twiddling your thumbs outside the station, waiting for your date to arrive (or perhaps pacing up and down panicking). You clock her as she is coming down the escalator, through the ticket barriers … and then you have a moment of stress when you realise you don’t know how you are going to greet her! 1 cheek or 2? Handshake, Hug, High 5 or something different?


    Trouble Shooting There are no right or wrong answers to this (but definitely forget the handshake.) The only thing to make sure of is that you actually make a call on how you are going to greet her and take the lead on it. If you are a ‘two cheek kiss’ chap, go for it, don’t pause awkwardly in between.

    Location Location Location

    You may have procrastinated over this one for days already, but before you confirm the reservation at Pizza Express, let’s pre-empt that and eliminate some red flags.

    location location location

    Trouble Shooting Location 1  Think twice about a restaurant. We’re not saying don’t eat, just eliminate its necessity. Why? Sitting down for dinner straight away can add to the awkwardness of an already awkward situation. Starter or just main course? Who pays at the end? Jug of tap water or a bottle of mineral water…? Don’t cause yourself unnecessary problems. Why not go for a cool bar with great (optional) food.

    Trouble Shooting Location 2 Prepare backup! We’d recommend always having a backup location, just in case. Perhaps it starts tipping it down as you arrive at a rooftop bar, or you walk into the gastropub and its rammed full of football fans. Yes, maybe you should be double checking this first, but don’t leave these things to chance.


    We’ve all had that awkward moment when sitting across from someone and thinking “oh s**t, I’ve no idea what to talk about”. Guess what? That situation usually happens on first dates. You may have conversed for hours online and on WhatsApp, with the most insightful, deep and witty conversations, but don’t overestimate your connection until the first rendezvous and have a trick up your sleeve.

    Trouble Shooting It might sound a bit weird to plan out your conversations, but it’s actually really important to make sure you have something to talk about if things start to get a little dry. But don’t stream of a ton of interview questions, steer more towards hopes, dreams and fun stories.

    How to Escape

    So you discover that her profile picture was errr… not quite accurate, or you discover 10 minutes in that she’s an absolute nutter. Either way, you need an exit strategy (and quick).

    Trouble Shooting You can always use the clichéd fake emergency call but surely you can do a bit better than that? Here are our 4 best strategies on how to make a swift exit;

    1 – Tell the truth. Ok, you may not go for this one, and it will definitely be super awkward but, TACTFULLY, saying how great they are but this isn’t going to work is a quick ‘rip the plaster off’ solution to the problem.

    2 – Set a time limit. So you realise early on that this is not a goer. Why not inform her early on in the date that “you need to be back earlier than expected so it will have to be a quick one”?

    3 – Man up. You’ve made a decision to do online dating, smart move, this is the best way to find that special someone, BUT you are unlikely to meet “The One” first time around and it’s just a reality that you are going to go on some bad dates. Deal with it. Sit there, smile and leave at a polite time.

    4 – If all else fails… Spill a large drink on yourself, ideally with a very unforgiving colour.

    The Send Off 

    The date has gone great and you want to make the first move. Hopefully, the confident greeting went well. Regardless, this is your second opportunity to display your confidence.

    Trouble Shooting So the trick with how to do this is to not overthink think it. Make eye contact, lean in and go 90% (We think Hitch got this one right) and leave the rest for her. She will either make the other 10% or divert to the cheek (or run away).

    So, we thought this handy little troubleshooting guide would help you in your quest with how to find your perfect match. Please do keep up to date with our further helpful posts… after all, this is why we are here.  

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