10 Important First Date Questions

21 Jun, 2022Dating, Relationships

10 Important First Date Questions

Jun 21, 2022 | Dating, Relationships

First dates can be stressful. And coming up with first date questions without sounding like you are interrogating your date can be tough

Let’s be honest. First dates aren’t much fun. They are really nerve-wracking and many of them are rubbish. And coming up with first date questions to ask without sounding like you’re a member of the FBI interrogating a serial murderer isn’t easy. Whilst also avoiding making it sound like a job interview. Add in all the stress of where to go and what to wear, it really would just be easier to stay at home and watch Love Island.

But when it comes to first date questions, there are many that can give you subtle clues as to whether you may want a second date or not. You can spot some potential red flags and save yourself a whole load of time and potential heartache. So I’ve compiled a list of the most important first date questions to ask and what to make of their answers. The devil is always in the detail.

First dates can be stressful. And coming up with first date questions without sounding like you are interrogating your date can be tough
First dates aren’t much fun. And coming up with first date questions without sounding like you are interrogating your date can be tough

Are You Actually Single?


I know this might be a bit obvious, but trust me when I say, there are a lot of men on dating sites that aren’t single. You may not get an honest answer, but you can look for some tell-tale signs such as a wedding ring line. It’s also much harder to lie to someone’s face and most people give away their lies with their body language. But if they tell you they are most definitely single but then proceed to tell you all their trials and tribulations and tales of woe about their ex, take it as a bad sign. If you get the bitter ex vibes from your date, or they are bad-mouthing their ex (I know we all do it but you should never do it on a first date), take it as a red flag and decline a second date.

The question should be met with a very simple straightforward answer, “Yes, I’ve been divorced/single for a year”. This is also not the time to ask if they are seeing or speaking to anyone else. It’s a first date not a meeting with the wedding coordinator.

Any answer that revolves around a non-understanding partner or living separate lives is your cue to end the date. Leave that mess for someone else to clear up.

Do You Have Any Pets? Are You A Dog Or A Cat Person?


When it comes to first date questions, this is more important than the are you single one. For me, dating someone that didn’t love dogs would potentially cause problems. My little doggy Derek is like another child to me, and I fully intend to get another dog soon. If someone came into my house and didn’t like my friendly little dog who would insist on a cuddle. I’m not going to cage the dog or put him in another room in his own home because you don’t like him.

Likewise, I really don’t like cats. They make me sneeze and I once had a terrible date that stank of cat piss. I’m probably not going to want to date a cat person. Sorry.

And you would have to have a heart of stone to not think my little Derek is absolutely adorable. Yes, he is very spoilt.

First dates can be stressful. And coming up with first date questions without sounding like you are interrogating your date can be tough

What Do You Do In Your Spare Time?


This answer can be full of red flags or give you some clues as to what you might have in common. It can also tell you if the person has the time to date you. Do they even have any spare time? Are their hobbies just time fillers or are they non-negotiables that they won’t drop to make time for you?

What does their choice of hobbies tell you about them? Fun-loving, adventure seeker or borderline alcoholic? The clues are always there. Be careful what you might be taking on. You also don’t want to end up in a situationship or a friends with benefits scenario.


Tell Me About Your Closest Friends


This first date question sort of leads on from the last as chances are they will have mentioned their friends at some point. Are they living out of their friends’ pockets, or do they have good supportive friendships with their own space too? Sometimes being the only single friend can be a double curse. Your friends want you married off so you can do the couples things but they also want you to stay single so they can live through your drama and have something to talk about. Are they staying single because everyone else loves the drama?

There’s a saying that you are the average sum total of the company you keep. So when your date is telling you about some not too nice elements of their friends, chances are, they are just as bad. Listen out for the clues. You may also have to spend time with these people in the future.

First dates can be stressful. And coming up with first date questions without sounding like you are interrogating your date can be tough

Tell Me About Your Work


Are they passionate about their work or are they just living for the paycheck? Are they ambitious or a workaholic? Being self-employed I am a self-confessed workaholic, but I’ve also managed to find the balance of switching off and not working 24/7. This can be hard if you are building a business, but no employee should be doing that. It’s worth remembering that your employer will replace you before your funeral has taken place.

I once dated a guy whose whole life revolved around his job. There was never a day off and he never knew what time he would be finished at. As much as it was great that he was so passionate about his work, I could also see from the outside that they treated him like a mug and he wasn’t even on that great of a salary. Work came before everything and affected every relationship he had, both friends and family. As far as I know, he’s still single.


Favourite Foods/Restaurants


Unless you want to be ordering two separate takeaways or having to sit through a dinner you really don’t like, favourite foods can be an issue. I have a nut allergy so some foods are completely out of bounds for me. So stay away from me peanut butter lovers. It’s also interesting to see if someone has good taste buds or if they are a food whinger. I remember a friend once dating a bloke who complained about every meal he ever ate. I did wonder if he had an eating disorder. We went out as a group a few times for a meal and it was just painful. He thought he was Gordon Ramsey without the actual culinary skills. I heard he could burn water. I would feel embarrassed for my friend when he would want to order from the kids’ menu in adult portion size.

A guy once asked me where I would like to go for a nice meal, his treat. Let’s get dressed up and go somewhere good. There was a new place I really fancied trying. It wasn’t an overly expensive place, just a nice menu and good reviews. He laughed at me and told me there was no chance he was paying those prices for a meal. I think he then suggested the Toby carvery. I suspected he thought a Happy Meal was a treat.

First dates can be stressful. And coming up with first date questions without sounding like you are interrogating your date can be tough

Have You Been On Holiday Recently? Favourite Place To Holiday?


This is a good way of finding out if you are on the same wavelength. Do they like to holiday in a tent or up a mountain whilst you’re more of a luxury resort with sunshine galore? I can tell you now, that I have never been camping in my life and rest assured, I never will. Nor will I ever do anything like climb a mountain or something that involves a canoe. And since I get horrific sea sickness, I’ll never go on a cruise.

I’m probably never going to date someone that doesn’t like a nice sun holiday. Ok so holidays aren’t a deal-breaker but if you’ve got expectations of a nice romantic beach holiday in Barbados and they are more a tent in Bognor then there are probably other areas too that you aren’t compatible in.


Have You Seen Any Good TV/Movies Lately?


I know people that watch nothing but football on the tv. Every single god damn day. Don’t get me wrong, I like football. I like going to games and I’ll watch some on tv. But there is no way I’m watching it every single day and spending all my Sunday glued to game after game of teams I don’t even support. Absolutely not.

The more you become a couple, the more nights watching the tv you’ll have. Best to find out now if you’ll be watching Match of the Day or Stranger Things then have to endure it through gritted teeth later and want to kick the tv.

There’s also the matter of personal taste. I like watching Love Island. I know it’s ridiculous and full of all the wrong types of people, but I get totally invested and enjoy the tweet-alongs. Now I wouldn’t expect anyone to sit and watch it with me, but don’t mock or ridicule my taste. It’s my guilty pleasure, not yours. Again, pay attention to the answers and the detail contained.

First dates can be stressful. And coming up with first date questions without sounding like you are interrogating your date can be tough

What Annoys You The Most?


This is actually a good one to see how honest they are. If they say they don’t know, they are lying. Everyone has a list of pet peeves. One of mine would be people who can’t give you their full attention without looking at their phones. Or the person I’m on a first date with, not asking me any of these questions. Or never asks me anything about myself or my day, work, family, anything. People that make everything all about them. People that poo in the downstairs loo. How impolite is that!!!!

If they tell you that bad timekeeping is a pet hate and you’re likely to be late for your own funeral, it’s probably best to confess now and see how they react. But if any of their pet peeves involve something about their ex, listen carefully. Are they bitter and petty? That could be you next.


Where Did You Grow Up?


This is a bit of a trick question when it comes to first date questions. You may already know this from Facebook stalking them but it’s the detail you want to listen to. Do they go off on a tangent about their hatred of their family? That’s all well and good if there is some bitter feud there, but it’s not a first date conversation topic. A person’s relationship with their family can be tricky for some to talk about, especially on a first date. Asking where they grew up gives them the opportunity to not talk about their family. But if they rant, a word of warning. Do you want to end up in the middle of someone else’s family arguments?

First dates can be stressful. And coming up with first date questions without sounding like you are interrogating your date can be tough

Bonus First Date Question: Ask About Their Kids


If they have kids, then naturally they’ll want to talk about them. Again, pay attention to the detail. Do they make time for them if they don’t live with them? Do they put them first? And if they swiftly move on to slagging off the other parent, then you’ve got yourself another red flag. Why? Yes, some parents are idiots and treat the other parent terribly. But it’s not a first date topic of conversation. If you bad-mouth your ex to me on our first date, then I will immediately think you will talk about me like that someday. And remember, there are always two sides to every tale. The truth often lies in the middle of those tales.

It’s really important to pick your first date questions wisely but to also make sure that your date is asking you questions too. A conversation is a two-way street. If it’s all one way, then ask yourself why?

Great Dates Advert
Great Dates Advert

Read My Latest Blogpost

Watch My Latest Video

What Is Work Life Balance?

What Is Work Life Balance?

Have you ever been told that you work too much? Do you feel that it is not really work because you enjoy it? Is there such a thing as work-life balance?

read more