To Ask Or Not To Ask... Your Guide to First Dates

To Ask Or Not To Ask... Your Guide to First Dates

iPlaySafe's Guide to First Dates

What to wear? Where to go? Have I shaved? What the hell do I talk about?! Anyone else freak out on a first date? As much as you can tell yourself “It’s just a date”, it’s not just a date, IT’S A DATE!

So how do you keep the chat flowing enough to unearth the person you’re sat in front of? How do you delve deep enough to get to know the true authentic self? Let’s face it, you might want to tear their clothes off but you need to be able to chat too, even if it's just small talk on the pillow the next day.

What are the red flags to look out for? Should I dive in and get some action the first time round? Is that bad? Well stop right there for a second. Who cares! If there’s mutual chemistry and you’re both up for jumping right in then go for it! Too often we ‘think’ rather than act. Sporadic impulsive moments can be magical. 

Let’s try and unpick some of the common worries around first dates. Just remember though, as much as I can try and steer and guide, you are the one sitting in front of another person. Be open, be honest, be authentic. 

What Questions Should You Ask on a First Date?

Plan your outfit, decide on the venue and then shimmy on over to these questions to help you on your communicative way. I’ve even taken a punt at deciphering the answers for you with a few tips along the way from the book Body Language: Learn How to Read Others and Communicate with Confidence (buy it and devour it!).

  • What’s your dream job? Their answer will tell you what their motivating factors are and whether they sit alongside yours. Their answers will also tell you whether they’re settled and on an ambitious career path or dreaming of pastures new. Whether you want stability or a dreamer is up to you.
  • Why do you like where you live? If you’re following up on date number 2 (or sacking them off and going for a new date) answers to this question will give you some ideas for future dates.
  • What do you like to read? Sounds geeky but answers to this can be fascinating and throw the door open to so many other discussions. Crime novels, biographies, mental health books, history, there is a whole pool of chat to dive into right there. 
  • Where’s your favourite place on earth? You’ll get the answer and it’ll lead to the question of why there, and from there possible insights into their lifestyle or travel desires. Who knows where you might find common ground.
  • Talk me through your friends? Date someone and you also date their friends. So get to know them well! You’ll also be deflecting the chat away from yourself if you need a break from the spotlight. 
  • Where would you like to travel to if you could jump on a plane tomorrow? In this Covid era who doesn't want to travel and this will open up a whole dialogue on destinations, desires, travel stories. And if the answer is “nowhere, I’m quite happy where I am” then run. Run fast. 
  • Name one person who has made an impact on your life? The answer to this will reveal so much about the person. Depending on who it is you’ll learn why they mattered, the nature of the relationship, the lessons they learnt from that person. Deep hey?
  • What’s the worst pickup line you’ve ever used? The answer to this is almost irrelevant. If they can’t have a bit of a joke with this question and engage in a bit of banter then don’t waste your time. Get flirty or get out!
  • If you could be a superhero who would you be? So much fun to be had with this question! Why do they want to be that superhero? What would be their ‘power’? Not only are you stepping away from possible ‘uncomfortable’ real life questions but you’re seeing how they respond to totally random curveballs. And let’s face it, life is full of curveballs!
  • Where’s the most random place you’ve ever had sex? Woah there! Too much? Yep, this one is possibly reserved for the second date, or the end of the evening when the banter has free-flowed comfortably, your knickers are feeling a bit fruity, you’re hot under the collar and in short, you’re at the point of wanting to step things up a level. Go for it, we dare you to shift gears. 
  • When was the last time you got tested? We’re not saying you should launch in with this as your first question, that would be a little intense. But, it's important to flag this and they’ll get the nod that sexual health is important to you. If you’ve met through iPlaySafe then you’ll be equipped with this info already and know that it really doesn’t need to be something awkward. If you’ve met through other channels then bring it up. If they recoil in horror, take that as a red flag. You want safety and sexual health to be treated with respect.

And here’s the awkward red flag questions you shouldn’t ask on a first date.

It’s a hard line between coming across as probing and wanting to get to know the person you’re on a date with. Ultimately, it’s very hard to know what to do other than try not to overthink things. So me listing questions about what to say is possibly not helping you! But here’s a few to avoid if you do need help. 

  • Why are you single? Since when was being single a bad thing?! It’s a life choice for many. Ask that question and you’re implying something is wrong with the person. It may just be that being in a relationship isn’t their ultimate goal, that they are quite happy being unattached. And from here, conclude that the fact they’re sitting with you on a date implies they’ve made the conscious choice to connect with you rather than pursue ‘multiple dates’ because they hate being single!
  • Do you want to get married and have kids? Err yep, back away from the future. Live in the moment, embrace the here and now. Don’t be a buzz killer by trying to plan your future before you’ve even road tested your potential spouse. Reign those thoughts in! 
  • How much do you earn? Do people even ask that question?! Apparently so as it made it onto eHarmony’s list of 20 questions not to ask so I thought it was worth mentioning. If it’s on the tip of your tongue, swallow that thought back down into the pit of your stomach. 

Red Flags - What Should You be on the Lookout For?

It’s all very well lining up the questions and what to avoid when you’re on the actual date but there’s also plenty to be mindful of beforehand. You’ve swiped and connected. You’ve hauled your backside off the sofa to interact with an actual human being. It's a gamble of almighty proportions. Do you spin the wheel of relationship fortune or not? Well, you know that if you want a relationship you actually have to meet the person so let’s arm you with a few red flags that will propel you straight back onto the sofa. 

  • The chat is as dry as your mouth post a big night out. When you know you know. If the chat over text sucks then it sure as hell isn’t going to get any better in person. Go with your gut on this one. Vague lukewarm answers just aren't good enough. Don’t waste your time. 
  • They mess you around with when and where to meet up. Once a flake always a flake. You’re enjoying their chat, got weak at the knees when you saw their photo but you cannot pin them down to meeting up. Do you really think you’re going to be jumping under the sheets with someone who can’t even commit to a coffee? Stop dropping the hints, act disinterested and move on. 
  • You’ve had sexual innuendos from the word go. Ok here’s the thing. Sometimes chemistry is so strong and overpowering that the innuendos are unavoidable and you’ve got to just fly with the wind on this one. Wherever the sex-infused gale takes you, go with it. But! Sometimes it can just feel a bit presumptuous, a little bit pushy, a smidgen inappropriate. Do they really want to get to know you or do they just want to get in your undies? Maybe you just want them in your undies too. Weigh it up. 
  • Your mate has set you up and you feel obliged to follow through with the date to please them. Why bother? Seriously, why bother. If the chat isn’t free flowing, you’ve stalked their social media and aren’t going ‘phwoar’ and you’re just not ‘feeling it’ then be honest. It takes just one line to your mate “I’m sorry I’m just not interested” and then you can all move onwards and upwards. Remember to say thanks though, always a fuzzy feeling when your mate has your best interests - and libido - at heart.
  • They open the conversation with “this isn’t something I usually do” or “I’m not sure what I’m looking for”. Oh right ok, now I feel really special! By stating their boundaries early doors they’ve already (wrongly) assumed you want to fall in love with them and spend the rest of your life with them on the first date. Telling someone before you’ve met them that they might not want to date you is about as sexy as Matt Hancock in a storage cupboard. You know what’s sexier? Netflix. In fact, anything on TV. Turn that TV on and stay home. 

Dating is complex, so complex. When you find yourself single with 2 kids it’s even more complex! The thought of swiping right (or is it left?) is petrifying. I have no idea what the rules of engagement are, who is supposed to make what move and when and how I'm supposed to behave. I can give tips and tricks, steer you away from awkward questions, steer you towards less awkward questions. And, I hope you’ve found some of them just a little bit helpful.

But surely all this comes down to common sense and intuition? Surely we’re all allowed to go with our gut, go with the flow, walk the lines of respectfulness whilst responding to chemistry (or not as the case maybe)? So from someone considering dipping their ageing toe into the world of dating, I’d say this. 

Be you. Be authentically and 100% you. Anything that makes you feel short of that leave it be. Be bold, be fearless. Be you. 

For more dating tips and advice, check out iPlaySafe's guide to dating in London, and get some inspiration for date ideas here. Make sure you get your play badge ready for your next date!

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