How to get better at dating

Image by the brilliant Stuart F Taylor

It’s rare that I get the opportunity to offer a really specific piece of advice. As a general rule, when people email me to ask “how do I get laid though?” or “can you tell me how to make people fall in love with me?” my answers will be the kind of fence-sitting waffle you’d expect from someone who isn’t paid per word to clickbait. Because the truth is generally not very clickbait-friendly. “Top ten ways you suck at dating” sounds way better than “well everyone’s attracted to different things and it’s all a bit more complicated than that.”

However, every now and then, something arises on which I can offer solid, useful advice. I’m as shocked as you are, but here goes – my number one tip for being better at dating:

Ask some fucking questions

That’s the advice, right there: to get better at online dating, you need to ask some questions. It sounds obvious, but I’m surprised to find that it’s not. I’ve recently had a fair few conversations with single friends about their dating experiences, and the most common complaint by far is that the people they’re dating seem to act like they’re at the wrong end of a job interview. They might offer a ‘what are you drinking?’ when it’s their turn to get a round in, but in between rounds they fail to carry their weight conversationally.

I appreciate that nerves can get to you on a date. I realise it’s easier to come up with some witty banter about why you hate your job than ask someone insightful questions about their own, but interest and attraction has to be a two-way street.

One of my friends explained that even when it comes to initial online dating contact – via messages or whatever the kids use these days – she’ll leap for joy if a potential date asks her something more specific than ‘how are you?’ There’s info on her profile, and a few easy pointers for questions (she’s got a fascinating job, and any suitor who simply asked ‘how did you get into that?’ would instantly leap to the top of her ‘would definitely shag’ list), and yet in the two years she’s been online dating, not one person has gone beyond ‘cool job. Fancy meeting for a drink?’

Of course, you don’t want to bombard people with a long list of questions that’ll put them off replying, but barring a few extreme exceptions, I don’t think anyone’s in danger of falling into Paxman territory. I spent a long time in the dating pool, and I can honestly tell you that I never returned home feeling like I’d been grilled by a potential partner. On the contrary: most of the negative dates I had ended with me feeling like a supporting actor in someone else’s performance – like I had only been invited so I could serve up a series of conversational feed lines, which my partner would then bat back before waiting for the next.

This attitude isn’t confined to dating – there are people who do this as a matter of habit, too, and it’s intensely frustrating. In one-on-one conversations, they will focus so hard on the idea that they have to impress you that they’ll interrupt simply because they’ve spotted a route in. You’re halfway through a story, or a point, and they go ‘oh that reminds me – let me tell you about X.’ Like your contributions are valuable only as inspiration, to tease more exciting thoughts out of their fascinating mouths.

Get better at online dating: ask questions

I don’t say this to make you feel bad if you’re one of these people. I say this because – halle-fucking-lujah – finally I have some generic advice that’ll work for most people who find dating difficult. For those whose dating failures are down primarily to the fact that they treat the event as an opportunity to impress rather than a mutually fun opportunity to find out about each other.

Can’t think of any questions? Struggle to remember them when you’re in the presence of someone awesome? Print these out and stick them in your pocket:

  • So how did you get into [type of job]?
  • What do you think of [place in which you’re currently dating]?
  • Can you recommend me a good book/film/TV show?
  • If you had to choose between being a unicorn or a dragon, which would you be?

Feel free to suggest more in the comments, and if any of those questions sound too specific/rubbish for you, then try some of these on for size:

  • Really? Ooh, tell me more.
  • That sounds amazing/scary/intense/exciting. Was it?
  • How did you feel about that?
  • Does that kind of thing happen often?

You get the picture. Essentially you just need to engage, in some way, with your date. Remember: this is not an audition, and you aren’t a starving actor who must leap through hoops for a part. It’s a friendly encounter between two people who may or may not end up fancying each other.

I understand why it happens. It happens because we’re so often told what to do and what not to do on a date in order to achieve this mythical dating goal: To Be Loved. We speak about dates as if they’re the first hurdle, and if we jump over that hurdle gracefully enough we’ll achieve some kind of dating win. Sex, a second date, the mutual exchange of rings, whatever. But we’re so focused on the win we end up spectacularly failing: like hares so keen to run towards the finish line we don’t notice that the tortoise has hopped in a golf cart and fucked off to the pub.

While it’s awesome to impress someone with your own anecdotes and jokes, if you don’t ask any questions of your date, then you’re giving them a whole heap of extra messages, including some or all of these ones:

  • I’m not interested in your opinion.
  • I literally only came here because I liked the photo: as long as you resemble it I’ll be happy.
  • If we are ever to enter into a relationship, I will never ask you about your day.
  • I literally couldn’t give a fuck about you.

Do you see? It’s pretty shit for the person on the other end of that: no matter how impressive your anecdotes are, literally nothing can counteract one of these messages. No one in the history of dating has ever had this conversation:

“What was your date like the other night?”

“Oh, it was amazing – [Name of Crap Date] was so funny and interesting, and has this fantastic job! I mean obviously they weren’t interested in my opinion whatsoever, but in all other respects they were perfect.”

Nor this one:

“How did your date go?”

“Awful. I mean, really awful. They seemed interested in what I had to say.”

“Christ, poor you. Better luck next time, eh?”

If you suspect you’re one of these people, then have a think about the average split of your conversations. As a general guide, you’re looking for roughly fifty/fifty, but if that seems too tricky then give yourself an easier target: three. Ask three questions. And none of them can be ‘how are you?’ or ‘did you find this place OK?’ Proper, actual questions about your date, after which you listen to the answers and – ideally – ask another question or two. Not nod through the first couple of sentences then go “ooh, that reminds me of this hilarious five-minute anecdote that I’m now going to tell you” or try to one-up their answer by anticipating what they’re about to say then explaining it to them “yeah, I’ve been to Thailand too. I don’t know about you but I found the whole thing a bit touristy.”

You might have lived an amazing life. You might have anecdotes and stories and jokes aplenty, perhaps even enough to create your own stand-up routine, which would keep a paying audience entertained all evening. But your date hasn’t bought a ticket to the You Show: they’re there to work out if the two of you are compatible. And you don’t have to be Paxman to get to the bottom of that, you just need to ask questions.

In summary: ask questions. Talk a bit less. Listen a bit more. And accept that sometimes the most impressive anecdote is the one you save for later.


  • This is great!! I can’t believe how many men don’t ask questions on a date – and you are 100% right as to how I interpret that behaviour. I hope people take your advice.

    I had to laugh at the timing of our posts today because I wrote about my new dating rules… which really are how to actually meet someone who is interesting and interested in dating, not just “hanging out”. Hopefully it will result in more conversational dates and fewer monologues :)

  • AnonyMan says:

    Totally agree. And your advice is more universal that that – it applies not just to dating but to ordinary social intercourse.

    As a man, I’m gobsmacked by the number of men (and it is almost exclusively men) who think conversation is a monologue. These aren’t the people I choose to spend time with after one or two encounters. Ofc I’m never guilty of such behaviour…

  • Bo says:

    Agreed. It’s worth noting that asking questions is, ceteris paribus, a good strategy.

    I use a bit of twatty Latin above because I’ve felt in the past like asking questions was not so good. There’s something about the written question which comes across as overly-interrogative, namely the question mark itself.

    Or, I might be curious about more than one thing about someone and ask TWO questions in a row (God forbid!) and then…silence. Then I’m thinking, “you fucking nerd, you’ve ruined it by coming across as too keen/boring/dull/intense. You SHOULD have made a witty comment instead, women like humour not fucking job interview questions”.

    Actually, as people are increasingly realising, who fucking knows why they didn’t respond. Probably they are too busy chatting to ten other people and your message/face didn’t cut the mustard. Maybe they decided to have a wank and delete the app (tinder obviously). Maybe they’re a robot. Fuck knows.

    But all other things being equal, asking questions is definitely good. Maybe it won’t be effective in every case, but then those cases don’t matter anyway and there’s nothing you could/should have done differently.

    It’s very disspiriting driving along conversations with people online who seem not to be interested in you. I don’t bother any more and just end them. What’s the point in giving of yourself to someone that hasn’t the manners or interest?

  • This is so true, I’ve been on so many dates where the guys or girls just haven’t asked anything – which drove me mad and left me feeling like a drill Sargent trying to fill the silent void with something to talk about.

    Another thing I hate is one word answers to a question. It can be like pulling teeth sometimes trying to get some form of conversation.

  • Chris says:

    *wry* The last time I was dating a man who wasn’t interested in anything I was doing, it turned out it was because he was only interested in no-strings sex, and was going through the motions of conversation just to get laid. So – yeah.

  • I know this is super bitchy of me, BUT….
    One time on this one blind date, I asked the guy (an American who lived near the Canadian border) where he would go if he could travel ANYWHERE in the WORLD. He said, “Canada.” Yeah. That date didn’t end well. I mean, sure, I slept with him. He was hot, and it was my first date in a long time, so…. Incidentally, he was the last date I had before I met my husband, and I was the last date he had before he met his wife, so, it all worked out. I hope he went to Canada on his honeymoon.

  • Jo says:

    OhmygodyesTHANKYOU. I opened up my OKC profile to men a few months ago and have only responded to guys who write me a question specifically based on something mentioned in my profile. So far, less than 5% of the messages I’ve received have contained such a question. As a conversation teacher, I never run out of questions to ask people. Examples: What movie villain scared you the most as a child? What book had the most impact on you as an adolescent? What film character are you most like? What’s the most trouble you’ve ever gotten into? When was the first time you felt like an adult? If you had to give up masturbation or alcohol for a month, which would be easier? Would you rather spend a week in the desert or in the rainforest? The list goes on…

    • abbirode says:

      I am about to leave for a first date in 10 minutes and I WILL be using those questions, they’re fantastic… I had come back to this post to re read it before hand. And this stuff is even better

      Thank you,

  • Bob says:

    I was given similar advice a couple of years ago, it’s very true. Personally, I find myself jabbering away not because I don’t care, but because nerves give me a huge bout of verbal diarrhea! I have tried, since this was pointed out to me, to actively stop myself talking and ask more questions. As others have said above, though, sometimes no matter how hard you try, it’s like pulling teeth. All you can get are one word answers, sadly I’ve been on those dates, it ain’t fun.


    Always be the dragon.

  • David says:

    So true! I discovered I made better connections interviewing candidates for jobs than I did in social situations. It’s because I clammed up and wouldn’t ask questions! When forced to ask questions in an interview, I naturally made great connections, particularly if they were interesting or qualified candidates. If a candidate was lousy, I lost interest quickly and found it hard to ask more questions. In reality, dating isn’t much different. Practice interviewing people.

  • L says:

    I asked my date and now boyfriend his views on cannabilism if that was the only option left. He laughed and it opened up a lot of questions.

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