Skip to content

The Two Essential Questions I Ask on Every First Date


A friend of mine in London writes an anonymous dating blog and I’ve occasionally thought about how lovely it would be to have an anonymous blog in which to record the many tales and funny stories about men, that I recount to my sister and closest friends over glasses of Aperol Spritz and morning runs together along the River Thames… I’m not sure why such strange and hilarious dating scenarios unravel before me in particular, but I’m a storyteller by nature and I do love to laugh and entertain my friends with my latest entanglements and the bizarre situations I find myself in when it comes to men. My friend Hannah even referred to me a few months ago as “the queen of dating” – which I think relates more to my many amusing tales, rather than as a measure of my actual success on the dating scene… Obviously this blog is far from anonymous so I’ve never been tempted to share these stories publicly, as I’m fairly sure that my blog is thoroughly scrutinised by any potential suitor or man I’m dating, and I’m not too sure such an exposé would go down very well with any gentleman suitor who found himself featured in a blog post about my love life!

        So for those exact reasons, I’ve never yet written a juicy “kiss and tell” post, and sorry to disappoint anyone in a nosy mood – this is not that type of blog post. But I do have plenty of opinions on modern-day dating, formed over the last year of encounters, dinners, parties and dalliances with the fearsome London dating scene.

        Now is just about the only time I envisage being able to publish such a blog post containing my musings on dating. Why? Well I’m nearing the end of a 4-month stint of enforced celibacy while living in rural Nepal, so there are no current suitors whatsoever to potentially annoy or offend. As a Team Leader out here, for obvious reasons none of my volunteers are allowed to touch me with a barge pole, and the immense language barrier between myself and every single local Nepali man I encounter leaves no room for any romantic sentiments. And it has honestly been blissful to be “single-and-not-looking” for 4 whole months. No anxiously wondering what a certain man thinks of me, no trying to remember what I’ve already worn on a previous date and no fretting over Whatsapp misunderstandings. And as there is no man currently on the scene, now is the perfect time to finally publish my musings on dating, before I return to London and get tangled up in that web all over again.


        In my opinion, the London dating scene is comparable to the job market in terms of competitiveness. It’s fierce out there! Attention spans are short, standards are incredibly high, the pool of available fish is huge and time is at a serious premium. As depressing as it may sound to hopeless romantics, the combination of all the above creates a serious requirement for efficiency. Urgh doesn’t that sound horrendous and jargoney. But in London, in between juggling work, a social life, travel and side hobbies, there simply is not enough time in the week to go about accepting invitations from just any old man. You need a filter of some sort. Previously I think my filter used to be along the lines of “What job do you do?” and “What subject did you study at uni?”. I used to think you could tell a fair bit about a person and any mutual interests you may have from those two questions, but now I’ve changed my mind and consider those two questions a bit boring. Over the last year of experimenting with questions to ask on a first date, I’ve narrowed it down to two essential questions that will pretty accurately determine whether the man in question and I will have any chance of suiting each other:

  1. Where have you travelled to recently? (the Background Check)

  2. Where’s next on your travel wishlist? (the Wanderlust Check)

         Question number 2 is the really key one here, as I’m far more interested in the future: in what sort of travel he aspires to do, where any of his plans might overlap with mine and where we might travel to together. I’ve realised that you can tell a huge amount about a person by how they choose to spend their precious annual leave, and I myself have quite defined ideas about what kind of travel I enjoy, so it’s a fairly simple litmus test. Question number 1 is a far more judgemental but necessary question to confirm the truthfulness of the answer to question number 2. Just like a job interview, I always expect a certain amount of first date chat to be creative exaggerations of the truth, in order to shine the very best light possible on the aforementioned “candidate”. It’s human nature to want to impress others and it’s very easy for a man to make up some exotic farflung destinations on-the-spot in an attempt to appeal to my inner wanderlust. While I would hope that the answer to no. 2 is truthful, question no. 1 is a reality check to see if they really do walk the walk, or just talk the talk. Where have they travelled to in the last 12 months or so? And I think these two questions are fairly useful for any singleton who’s interested in travelling to have up their sleeve. Satisfactory answers to these two questions make the decision of whether or not to accept a second date a piece of cake.

In my case, there are a few examples from last year that jump to mind to better illustrate my point.

        “Exhibit A” is a young gentleman who, over a bottle of white wine on a sunny afternoon in Parsons Green, declared to me that his favourite city in the world to visit is Dubai. His blatant mention of his British Airways Exec Club Gold status was impressive, but ultimately was delivered a tad too boastfully, thus cancelling out any brownie points gained by that snippet of info. But the primary issue with my wine companion that afternoon was the word “Dubai”. I’ve never been to Dubai personally, but the impression I have of the city is not a good one (I’ve heard of a big divide and separation of Western expats from local inhabitants, a scarcity of culture and little else to do beyond party and shop) and it certainly doesn’t feature on my travel wishlist anywhere soon. If that is his idea of an ideal trip then we have some pretty significant differences. His answer to question number 1 was equally disappointing: Miami and New York. Apologies but, with zero appreciation for culture or adventure, it was a no from this corner.

          In a Chelsea pub one summer afternoon last year, “Exhibit B” and I were in the middle of a fantastic conversation about volunteering and travelling around South Africa – his most recent farflung trip, and all seemed to be going swimmingly. Upon asking what he had planned for the rest of the summer, he rather sheepishly owned up that his only trip abroad in the next 6 months would be an annual golfing holiday on a Spanish coast… Golf? Every single year? On a Spanish coast? A one-off I could have dismissed, a father-son bonding trip I could have ignored, but it just jarred as being at the polar opposite of the spectrum from my own travel plans. And the reason for it being his only trip abroad in 6 months? He coached a semi-professional rugby team every single week so basically couldn’t let down his team for weekends away, etc. Long weekends away feature very heavily in my life so it simply never would have worked.

         “Exhibit C” was handsome, funny, arty, spoke a few other languages, and we had lots in common (including living just three roads away from each other at the time – awkward). Over a picnic one summer’s day (you can tell I like daytime dates) he told me about his wish to travel around India and an upcoming trip booked to Madrid. Having lived in Madrid I revelled in being able to suggest lots of different galleries, restaurants, etc. and all was progressing very well. Until Burning Man happened. He went to Burning Man in the US and some random niche festival in Sweden, and at this point I remembered that I am no way near cool enough for those music-festival-types, nor can I bother to pretend to be cool enough, so I called it quits before he discovered it for himself. It’s not that I don’t like music, as obviously I do, but there’s a kind of East London & festival music snobbery that I just really dislike, and from past experience I know that it makes me feel very inferior, and I haven’t got time for any of that.


         And last but not least, “Exhibit D” was a very well-spoken European with a number of languages, impressive travel and academic record, and incredible humour given that English was not his mother tongue. And yes, although I would love to visit Argentina and Uganda one day in the future, was the very first date a little too soon for him to invite me to visit both countries with him in just two months’ time? Perhaps a tad too keen? There’s a difference between sweeping a girl off her feet and coming on way, way too strong. But high marks to him for originality – strong destinations and an enticing offer, just need to work a little on timing…

          While travel is for very obvious reasons a key topic of conversation for me with anyone I meet, I know that it’s not of equal importance for everyone. You may agree or disagree with my light-hearted hypothesis about the two essential questions I ask every potential suitor, but so far I’ve found travel to be the topic that reveals most about a person, without having to dig too deep into their inner psyche or appear too nosy… It might seem a judgemental criteria to some people, and I suppose it probably is. But if a first impression made on a first date is not judgemental then I don’t know what is! If I were a true journalist, I would have loved to ask my 4 “exhibits” for an anonymous comment each on what aspects of my travel style they did or didn’t like… It would have been a fascinating experiment!

What do you think of my two essential questions and my theory on the London dating scene? Do you agree or disagree?


  1. Can you give me C and Ds numbers, or Snapchat codes, or whatever people do these days? They sounds great. Love that you filter by travel passion, I think I do the same but subconsciously.


  2. How interesting that London is awash with good candidates. We in the sticks struggle horribly to even find someone to date, who has a degree or is vaguely well presented. Maybe I should move?
    Finally after a long gap, I have two dates today. I shall try your questions!


    • It’s chaotic in London, and would all be far easier with less choice! And two dates in one day – very efficient! Hope these questions help hehe


  3. First impressions make or break the deal, in my opinion, so I completely agree with you. Thought provoking article…one’s travel destinations tells a lot about them.


  4. I’m out of the game now but I like your questions 🙂 I’d feel initially a bit awkward though if both answers were “nowhere” and “nowhere”. Not everyone can afford to go travelling on a frequent basis and I’d instantly be trying to hide my surprise and then start downplaying my recent trips so as not to sound like one of those people who borderline “brag” about going everywhere all the time … and then I’d start overthinking everything anyway 🙂 Good job I’m sorted now lol


    • Haha the only conversation I have is travel, so if the answers were ‘nowhere’ then there’d be a very long awkward silence haha! Glad you’re sorted too, you sound so perfect for each other


  5. I loved this post, and thank you for the shout-out to Mad Blogs & Englishmen! I have the exact opposite problem – everyone on all these apps seems to have a passion for travelling and my heart sinks when a date asks me either of your two essential questions! It’s interesting what you say though about how travel comes in so many different guises. Golf holiday, lol.

    I wonder, do your dates always know about your blog before you meet? And could you ever conceive of falling for someone who’s not passionate about travelling?

    And… what would you say to people – like me – who don’t have a strong desire to travel to persuade them to ‘try’ it? I’d love to read a post on the subject.


    • Thank you! And sorry to be another one of those annoying people! And yes most of the time I think they do know that I have a travel blog as I mention it, but perhaps not what it’s called or how to find it.

      And regarding falling for someone not passionate about travelling – probably not. I wouldn’t want to cut down on my travel, nor travel alone, nor feel like I was dragging him around with me against his will, and I want to move abroad again at some point, so that would be a big factor. And besides travel, I really have very few other interesting things to talk about so I’m not sure what we’d have in common!

      And that’s such a good idea for a blog post – I will have a proper think and get back to you on that! But my short answer would be: perhaps link it to something else you love doing, like dancing for example. Take dance classes/courses in different countries around the world, like tango in Argentina, salsa in Cuba or ballet in France, and learn their culture through their style of dance and ease yourself into travel through a passion you already have. It could also work with food, with music, with making art – almost any hobby you have in the UK will have another form or style elsewhere in the world, and learning about it is a good introduction to another country. But I will have a proper think and write up a full blog post too!


      • Not at all! I think it goes to show that it’s a useful way of assessing compatibility, especially if travel’s a really important part of your life. By contrast, I get (pathetically) excited when I meet someone who’s not afraid to admit that they have no strong desire to travel!

        That being said, linking travel to a different passion, like dancing, is a really good idea. Cuba and Argentina… hmm… food for thought!


What do you think? Leave a comment

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: