The 20 questions every man should ask on his first date

The 20 questions every man should ask on his first date: After one woman laid out her checklist for the ideal man, this 58-year-old bites back with his own debut hook-up audit

After eight years of single life, I’m looking for someone to spend time with and do nice things together. It’s not too much to ask — is it?

But as I read Julie Silver’s 20 questions for a potential partner last week, I was reminded how much of a minefield dating can be.

In Julie’s case, her Mr Right would prefer quinoa to chips, would be in her specially adapted inclined bed by 9.30pm each night, speak kindly of his mother, be a fan of natural cosmetics and wouldn’t have a dog.

You may think she is being too ‘picky’. Yet I can tell you, it’s not just women who have a list of specific questions in mind before a first date. Single chaps like me do, too.

In my case, they include establishing whether my potential Ms Right is a fan of hiking (yes please), reads in bed (ideally not) or posts pictures of her breakfast on Instagram (a definite turn-off).

After one woman laid out her checklist for the ideal man, David Sanderson (pictured) bites back with his own first date audit

While I’m usually attracted to petite, brown-eyed brunettes, it’s far more about personality. But I won’t lie: a Penelope Cruz lookalike would be heavenly.

So what do you need to know about me? Friends say I’m not a bad catch. At 58, I’m 6ft 1in, slim, have my own home, my own business and, with two daughters in their late teens, I’d like to think I understand a bit about women.

I married in my early 20s but that lasted less than 12 months. I was a helicopter crewman in the Royal Air Force and the long postings away spelled disaster for our relationship.

I later fell for somebody I’d known since school and although we never married, we were together for 13 years. We had two daughters, who are almost 20 and 18, but split in 2014, having gradually grown apart.

I live in Oxfordshire. After the split I spent five years focusing on setting up my estate and lettings agency. Then Covid came along and I spent lockdown on my own, which made me realise I did want a relationship. Yet just as we were allowed out, I snapped an Achilles tendon playing cricket, which hampered any dating efforts for more than six months.

I’d love to find that special someone to spend the rest of my life with. The question is, how?

My recent dates have all come from dating apps. It can be hard work dating online but for every bad experience there are also lots of very nice singletons out there. I’ve actually become good friends with a couple of them.

When I do go on a first date, although I make sure to subtly weave my questions into conversation, the answers will tell me if we’re a match made in heaven or utterly incompatible . . .


1. So what happened with your ex?

I’m happy to explain why my last relationship ended and I hope my date could be just as candid. I’m not digging, it’s just nice to know why things went wrong. If your ex and I sound too similar in personality, what annoyed you about him will probably annoy you about me.

If the ex is still firmly on the scene, it’s probably a no-go for me. The same applies to anyone who only recently split; you won’t be properly over them — I wasn’t when I split with the mother of my daughters. We’re still in contact about them but we don’t speak often.

2. Do you spend much time on social media?

I don’t get the point of it. I needn’t follow someone famous to get beauty advice. Scrolling through images of dogs wearing silly hats? No thanks.

I particularly dislike people posting online what they had for breakfast. I was at Gatwick once and a friend rang to ask ‘How are your eggs?’ We hadn’t even left the country and already the person I was going away with had snapped our pre-flight meal and posted it on Instagram. I don’t want my whole life on display.

Do you spend much time on social media? David Sanderson says ‘I don’t get the point of it. I needn’t follow someone famous to get beauty advice. Scrolling through images of dogs wearing silly hats? No thanks’

3. Are you a soaps fan?

I’d FAR rather listen to contemporary music than plonk down in front of EastEnders or Coronation Street. However, classical music does nothing for me. Listening to live music is another big attraction, but I prefer small gigs.

4. Do you read before bed?

When I go to bed, it’s for a cuddle or to sleep. Yet one ex insisted on reading for hours. Even if we went to bed at 11pm, the bedside lamp would click on and I’d be kept awake by the sound of page-turning. It drove me nuts!

5. What are you passionate about in your spare time?

Hopefully something outdoorsy or fitness-based. I love being surrounded by nature, walking and swimming. I also enjoy skiing and the gym. If you’re a gym bunny or a runner, the odds are we would get on. But everything in moderation — if it’s something you do for hours a day, would I even get to see you? My nightmare would be someone who cites meditation as their hobby.

6. How do you prefer to spend your time on holiday?

Time off for me means relaxing by the pool. While I like a bit of culture, a whole week of visiting museums and art galleries would be too much.

I enjoy weekends away in this country but if your dream destination is Blackpool, we won’t get on. If the answer is Bath or Bristol for the cafe scene, or the Lake District and Scotland for walking, great.

Do you read before bed? ‘When I go to bed, it’s for a cuddle or to sleep. Yet one ex insisted on reading for hours. It drove me nuts!’, says Sanderson

7. What’s your attitude to booze?

WHAT I really want to know is, ‘what kind of a drunk are you?’ I’m not a big drinker — after a couple of glasses of wine I get a bit more tactile, then usually want to sleep. Not everyone tipsy is the same, though. I’ve known women who get feisty and want an argument, ruining the evening for everyone.

But if you’re teetotal and don’t drink ‘any more’, I’ll want to know the history behind the decision.

Drinking a whole bottle of wine every night would be a bit of a red flag. Ditto those women who can down pints as if they’re going out of fashion. What I’m hoping to hear is that you’re a half a bottle of prosecco or cocktail kind of girl.

8. Do you own a pair of walking boots?

I HOPE you have more pairs of heels than walking boots. But walking is very important to me, so hopefully you will have a pair in the wardrobe. My parents live in Cornwall and there are breathtaking coastal walks. There are also lovely walks in the Cotswolds near where I live, and I enjoy a good three to five-mile walk, ideally with a pub lunch at the end of it.

9. Do you like garlic and cooking?

I LOVE cooking and experimenting in the kitchen. Having a traditional Sunday roast or bland food every week is a boring prospect.

I like talking over a freshly made meal — I’m an Aquarius, we’re very sociable and like to chat. Sharing food is important and dating a vegan might also prove difficult. No constant checking of phones at the table is obviously a given, too.

10. Do you have any pets?

Too much pet talk is a passion- killer. I really like dogs but I’m not a fan of the trend of treating them like babies and allowing them all over the house. I’m not a cat person and if someone told me they had a menagerie of pets, I’d know we were chalk and cheese. Trying to plan dates and romantic foreign holidays around petcare arrangements isn’t something I want.

How do you prefer to spend your time on holiday? Is it relaxing by the pool or searching for culture with a whole week of visiting museums and art galleries

11. What films do you like?

If IT’S obscure foreign films, I fear we won’t go the distance. I enjoy mainstream films and am not ashamed to say they can bring a tear to my eye. I recently saw the new Top Gun film with my daughter, having watched the first one in 1986, six months before I joined the RAF aged 23. I lost some good friends and colleagues along the way, just as Maverick lost Goose. So one line was very poignant for me: ‘If you fly long enough, you’ll lose someone you care about.’

12. Have you had any tweakments and enhancements?

This is such an awkward question for a man to pose to a woman, and one I wouldn’t be brave enough to ask outright. At this age it’s kind of expected and I don’t actually mind subtle work such as Botox, teeth-whitening and some fillers. But I’m still not a fan of those pouty fish lips.

I believe it’s better to just exercise, eat sensibly and be natural. But if it makes you feel happier and more confident, that’s fine.

13. Do you want to have children?

Eek. At 58, I definitely don’t want any more but I love the two I have. I was a late starter as a dad, having my eldest daughter at 38 and my younger one at 41. I certainly don’t mind a woman having children but, while I wouldn’t rule out someone with younger children, I’d prefer it if they were grown up.

Luckily, with most of the women I’ve met — my age bracket on dating apps is set to 50-60 — starting a family isn’t an issue.

14. What kind of family are you from?

I’m AN only child and my parents, to whom I’m close, have been married for 60 years. So for a potential girlfriend it would be nice if they had a similar relationship with their folks. If they didn’t, I’d want to know why — and if it was negative, it would probably sound alarm bells.

15. How important are romantic gestures to you?

I’M NOT Mr Romance. A former business colleague only ever bought flowers for his girlfriend when he’d been unfaithful to her, and to this day I think of flowers as a sign of guilt.

I’m OK with public displays of affection and will hold hands but I’m not good at public grand gestures. If someone starts singing Happy Birthday in a restaurant, I want to crawl under the table.

So if you want to be showered with bouquets and chocolates, I’m not the man for you. But I do listen to a partner and mentally note down things you like, hopefully surprising you on your birthday or Christmas with something I’ve remembered from months back.

What’s your attitude to booze? In other words, what kind of drunk are you?

16. How do you like to relax?

If it’s solo health retreats, meditating or putting your favourite crystals out under the moonlight, we’re definitely not on the same page. If it’s being outdoors or exercising together, it’s a yes. I like spending time as a couple, talking, going on holiday and spending quality time with you.

17. How important is personal hygiene to you?

Again, this isn’t something I’d ask outright. As long as you look good, smell nice and aren’t too hairy, I’m happy with that. As for taking over my bathroom, I always have shampoo and conditioner but I expect to lose some shelf space in the bathroom if you stay.

18. How do you prefer to communicate?

I TEXT more than I call, and some women don’t like this. My argument is that people can read my message when they’re not busy. Yet I’ve been told more than once by women that nothing beats hearing the sound of their beloved’s voice. So if you want long luvvy-duvvy phone calls every day, we won’t be well suited.

19. Do you like confrontation?

I’m not very good at confrontation and don’t like a full-on argument. I swerve women who believe that having a massive ding-dong followed by make-up sex is proof of undying love. When it comes to conflict, it’s more about choosing your battles. As someone wiser than me once said, ‘Do you want to win the argument or do you want to be happy?’

20. Do you want to get married?

This is a question for down the line but I’ve been married once and it wasn’t very successful, so I’d rather live happily together without ever saying ‘I do’. However, if it was important to you, then I would consider it.

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