10 Questions To Ask Before Going On A Third Date With Someone You’re Not Sure About

At this point in the year, let’s be honest, dating is exhausting. Cuffing season started long ago, and while your friends put the work in early and guaranteed themselves a Christmas present and Winter Wonderland date, you sat back and thought ‘eh, one more episode, bar-hopping can wait.’ And now you’ll be lucky to get a ‘Happy Xmas’ text.

It’s these exactly at these times of year, when everyone else is getting cosy with the person they were ‘just casual’ with all Summer, that we start to think ‘hmm, maybe that guy maybe that guy who sells novelty socks on Facebook marketplace and “doesn’t believe in soap” wasn’t so bad?’

But come on, Christmas or not, there is no valid excuse for letting your standards slip. So, in an effort to remind us all of our fabulous worth, regardless of relationship status, here are the 10 questions to ask yourself if you’re not quite sure about the person your dating. Here’s what you should be asking…

1. Why am I going on it?

‘I dated a lot in my twenties,’ says Charlotte*, 55, ‘I absolutely hated it, but I would force myself to go on date after date with the same boring men because I felt like it’s what everyone was doing, like I should be proactively looking for someone to spend my life with. It gave me some funny stories, but if I could go back I would shake myself and be like “relax! You don’t NEED to get married or have kids or find a ‘soulmate’ if you don’t want to!” That way of thinking is so restrictive, I think we just need to take the pressure off and if you don’t want to date, don’t! There’s so much more to life’.

2. Do I actually fancy them or is that we just get along well?

‘When you are a few dates in and you’re still having a great time – a similar sense of humour, loads in common, always easy to talk to about anything, but you don’t actually want to rip their clothes off, they doesn’t make your heart race faster and your appetite is never diminished by a fluttering tummy, then you may well have just got yourself a potentially good mate, rather than a romantic partner,’ says dating coach Jo Hemmings, ‘If initial attraction or chemistry isn’t there, or it’s just not happening after three dates or so, then it’s unlikely to happen at all.’

3. Do I just want a free meal?

‘When I was dating I used to rely on it purely for a nice dinner on a Friday night’, says Tasha*, 30, ‘if I was ever running low on food in my fridge I’d just start messaging guys that had taken me out that I knew would do it again. It’s fool proof, but I didn’t actually like any of the guys, I was just living my best life.’

4. They’re great, but they wear odd clothes and have a few funny habits, am I being too picky?

‘Being critical of your partner some way down the line is often what happens,’ says Jo, ‘You might feel they needs to smarten themselves up, make a bit more effort or spend less time watching sport and more time doing it. Or they might have a quirky habit, or a way of saying things that is a bit repetitive or predictable, but these, especially during the first few dates, should be endearing rather than irritating. That comes much later! So, if you’re already feeling like you want to change something about them, then that is probably a major red flag that the relationship probably isn’t going anywhere fast.’

5. Is it worth getting out of your PJ’s?

‘I was once on a date with this guy that I’d met a couple of times,’ says Ellie, 25, ‘I’d reasoned on the first date that he was shy and that’s why there wasn’t much going on personality wise, then on the second we’d seen a film so there was zero talking, by the third I realised he was as dull as a bar of soap and I spent the entire time daydreaming about getting in bed and watching TOWIE as soon as possible. Now I know, if he’s not worth missing TOWIE then it’s a hard no.’

6. I'm not sure I trust them, should I continue dating them?

‘In the early stages of dating, especially after a few dates, we expect that what we are being told is honest,’ says Jo, ‘Sure, it might be embellished a little for entertainment value or to impress you, but essentially, it’s the truth. If you start having doubts about that or they’re telling you something that doesn’t quite ring true or match what they have said before, then you may well be with someone who is not being totally upfront to you or perhaps even seeing someone else. If you’re instinct sys that something isn’t quite right, then trust it, it probably isn’t.’

7. Are you scared of being single?

‘Dating after my first serious relationship was terrible,’ says Sara_, 26,_ ‘I went out with two different guys for far longer than I should’ve purely because I hated the idea of being single. Looking back, I should’ve cut them both off after the second date and worked on my own shit, I don’t think you should ever use dating a distraction from your own pain, you just have to face it.’

8. Do they make you feel good about yourself?

‘Your date should be making you feel good about yourself,’ says Jo, ‘If they’re undermining you in any way or you get the feeling that there are things about you that they’d like to change, or they’re not quite accepting you for who you are, then you might well be dating someone who wants to control you, is gaslighting you or may even be a narcissist.’

9. Could it all be worth it if you meet someone you love?

‘I went on five bad dates with my husband before I actually liked him,’ says Jenny*, 33, ‘I really don’t know why I put up with it for so long, I think I was just bored to be honest, but by the fifth date he came out of his shell and we just clicked. Now, obviously we’re married and everything is amazing, but it was a definite slow burner.’

10. Do they listen to you when you've had a bad day?

‘While no one wants to date some who is always grizzling about their boss or work issues, your partner – even at the early stages of a relationship – should be there to comfort or reassure you if you’re feeling sad, emotional or just having a bad day,’ says Jo, ‘If they don’t offer you a hug, or shoulder to cry on -virtual or otherwise – seem distracted when you talk to them or even tell you that you’re being silly or over reacting, they might lack empathy and emotional intelligence. Every couple needs to be able to share, from time to time, when they are having a tough time at work and at least feel that they are being listened to and an effort is being made to cheer them up.

Want specific dating advice from Jo? Visit her website for more information__.