Dating challenge complete! I chatted up a man in real life

Image by the fabulous Stuart F Taylor

This man has spent the last twelve months greeting me with eager smiles each time I see him. When I walk into the shop, he looks up and sees me then beams a fully radiant grin. I return it with gusto, and he smiles even more brightly. Something about this guy’s warmth makes me want to get to know him better. But something in every fibre of my being recoils at the idea of being bold enough to actually ask him out.

I’ve told you a little about this guy before, in a blog about how bored I was with dating sites. I think I’m pretty good at writing online dating profiles, but there’s no point having a decent one myself if the only men I’m shown have profiles that wildly mismatch: ones that consist of a couple of lines that tell me nothing about who they are. Those who did have decent profiles often sent messages that trashed all that hard work: ‘how are you?’ or sometimes, if they were feeling adventurous, ‘how are you today?’. Eventually, I developed an almost Pavlovian eye-roll response every time I opened up an app.

Dating isn’t meant to be a chore, it’s supposed to be fun. So I made a list of fun things I could do to try and meet men in real life: speed dating; Pear Rings (more on those later); blind dates; pursuing hot shop man… you get the idea. That last one required the most bravery. Asking a man out before I’ve even had a chance to check his vital statistics (monogamous/non-monogamous; single/attached/married; straight/gay/bi; has children/wants them; religious/non-religious; lefty/centrist/right-wing-and-therefore-undateable – there are LOTS) was scary enough. Could I actually approach someone whose name I didn’t even know, outside any kind of ‘dating’ framework, who I’d only ever spoken to when stone-cold sober between the hours of 9 and 5?! I’m not just out of practice with this kind of chat-up, I’ve literally never done it. I am basically a ‘shoot your shot with a hot guy you vaguely know’ virgin. Sure, I’ve drunkenly slurred ‘I love sucking dick’ at baffled men in pubs, clubs or at parties, and I’ve definitely made the first move with guys on dates if I think they’re too nervous to ask me ‘your place or mine?’.

But speaking to a man I fancy, with whom I have no friends or colleagues in common, who I have no idea is even available, in an environment that isn’t a pub or club? How bold! How scary! How… American?! I can’t remember ever doing this kind of chat up. Over the course of my life, I’ve done more fucking bungee jumps than I have this sort of thing. And the jumps were far less scary.

So even as I put it on The List, there was a part of me that hoped I could leave this particular dating challenge till last. After all, if the speed dating or blind date plan worked out and I scored myself a boyfriend, perhaps I could swerve the Big Challenge altogether. Maybe I’d never have to stand in front of this warmly-smiling, beautiful, friendly guy and hand him a scrap of my self-esteem along with a mumbled: ‘How about it? Do you like me? Can I buy you a pint?’

But often when you’re lacking in bravery, getting people to dare you can help with a confidence boost. On a recent live call I read my Patreons a preview of that post, and asked them which dating challenge they thought I should tackle first. The answer was almost unanimous: Shop Man.


Dating challenge tip: take a run-up

I’d love to tell you that I marched straight off to the shop, batted my eyelashes at him, and launched immediately in with smooth chitchat, escalating neatly and consensually and wittily from the brief discussions we’d had in the past. But honesty’s the best policy, so in fact I’ll confess that I took a bit of a run-up.

I began by escalating a little – testing the waters so it didn’t feel as frightening. Not only was I worried for my own ego if I marched up to him, said “DATE ME?” and received a ‘hell no’, I was also painfully aware of the consent issue that rears its head if you’re trying to romance someone within their place of work. I wanted to make reasonably sure that he wouldn’t feel awkward or pressured if I asked him out, so a gradual escalation which he could back away from if he wanted felt like a safe place to start.

Next time I went in, I spent a bit more time talking to him than usual, asking if he had any fun plans for the weekend. That was my first mission: to ask him that question. I figured it was a little more open than some of the things we’d spoken about before, and gave him the opportunity to either be expansive (“oh I’m off to the cinema, I really love horror films, how about you?”), or shut things down (“not much”) if he wanted to.

Naturally I timed my visit for a day when I knew he’d be working. And I did it at the end of the day, when I was heading out to meet some mates so I looked vaguely presentable: hair brushed and eyeliner on and wearing my least-rubbish hoodie. Showing off that I am in possession of a sparklingly fun social life, and demonstrating that I’m not always the sweaty mess who stumbles into his shop after a bike ride or a walk. I bought some things from him which I definitely didn’t need, and when I asked if he had any plans he was incredibly expansive: told me what he was up to, asked what I had planned, probed a little on where I was off to and then told me to have fun at the gig. Mission one complete: this man was definitely more than happy to chat. I was pretty sure he didn’t want me to fuck off, wasn’t purely being polite because I’m a customer, and wouldn’t feel uncomfortable if I actually asked him out.

The next time I went to the shop, I set myself a new challenge: still not yet ready to ask for an actual date, I told myself to try and learn his name. That felt like a nice escalation: learn his name. I reckoned a proper introduction, coupled with the fact that I couldn’t possibly need as many Shop Items as I was currently buying, should be enough to hint that I was keen to take him for a pint/snog him under a tree while the sun set, gently stroke his hair and smile coyly, then let him grab my bum and tell me I’m beautiful.

I deliberately dressed up for my next visit. This is extremely unlike me, but fuck it – the dressing up gives me a tiny bit of confidence, and I figured in lieu of alcohol I’d take all the help I could get. I put on my best jeans, a shirt that opens just enough to show a hint of tits, a jangly necklace that draws attention to aforementioned tits (“BEHOLD! My tits!”), a bit of foundation and eyeliner, and the cloak of confidence that I pop on when I’m trying to pretend to be normal. Spotting one of his colleagues at the counter the first time I walked past, I cursed the Shop Gods and kept walking, detouring around the block a few times until I saw that lovely Shop Man had emerged from the back room and was chatting to another customer.

OK GOTN, this is it. Your chance. Introduce yourself.

YOU CAN DO IT. Let’s go!

Tip 2: Remember the goal  – it’s not to get a ‘yes’, it’s just to ask

The key thing I’m reminding myself is that the goal of the ‘dating challenge’ is not to get Shop Man to marry me. Nor is it ‘seduce Shop Man into bed and wow him with my oral skillz’. The challenge isn’t even to ‘score a date with Shop Man’. The challenge is simply to ask. If he says ‘no’, that’s still a win, because he can only say ‘no’ if I’ve asked the question.

This is super important to me, and probably to you as well if you’re also a big shy nerd whose previous dating experience is mostly based on swipes. I have no control over whether this man will want to date me, so that can’t be the goal. Not only do I not know his vital stats (he could be gay, or married, or taking a dating break for his mental health or something), I also have no idea if I’m even his type. Maybe that warm, friendly smile is one he gives to all the customers and I’ve just misread the signs. More importantly, remember the consent thing from the start? I’m approaching him in his workplace, which is potentially shaky ground. Any date request must be made lightly and casually, so it can be immediately walked back if I sense any hint of discomfort. The goal is not to get a ‘yes’, the goal is just to ask.

Academic though, really, because today I’m only planning to introduce myself. Asking him out is still Too Much for this trembling bag of insecurity.


Except… when I walk in, he beams at me as he always does, and immediately comes over to say a proper hello. Before I can even stutter out an intro, he’s asking me about last week’s gig: how was it? Did you have fun? Did you go on anywhere after? I grin back and we get stuck into a chat. I tell him about my passion for any and every band that has the word ‘brass’ in the title, and hunt for an opportunity to slip in an introduction as we move on to discussing this weekend’s plans.

He’s dialled up the friendliness at least two notches since last week, to the point where I suddenly become convinced that if I don’t ask him out right now, he’ll ask me instead.

“Absolutely not!” My brain interjects with horror. “If HE asks YOU then you haven’t completed the challenge! Remember the point is not to GET A DATE, the point is to ASK SHOP MAN OUT. If you do not do this IMMEDIATELY then you’ll have failed yourself and – more importantly – failed all your lovely Patreons.”

So, like a commenter racing below the line to hammer out the word “FIRST!”, I quickly ask him out.

In the moment, it really is that easy. In fact (if I say so myself) it’s actually pretty damn smooth. Channeling the spirit of someone who knows how to do this (probably an American with shiny teeth and a sports jacket and a name like Brad or Chad or D’Angelo), when Shop Man casually jokes that he’s got some fun stories about travel, this weirdly smooth and confident version of me replies:

“Oh really? Maybe I could buy you a pint and you can tell me those stories sometime?”


The relief/joy/triumph which rushed through my veins as I got to the end of that line must have been visible on my face, because Shop Man grinned in apparent triumph too and replied immediately:

“Yes, I’d love that. What are you up to this weekend?”

Dating challenge tip 3: remain smooth at all times

As I say, the point of this was not to get a ‘yes’, the point was just to ask. But obviously the ‘yes’ was a very nice bonus. The ‘yes’ gave me a shot of genuine confidence, which replaced all the pretend stuff I’d conjured before I walked into the shop. Never in my life has the phrase ‘fake it till you make it’ hit me with such clarity: I faked a bit of swagger, did a scary thing, and as a result my actual confidence grew two sizes in an instant. MAGIC.

In a way his ‘yes’ is annoying, because I’d love to have seen how this post would have turned out if I’d asked him (thus completing the challenge) and he’d said no (thus rejecting me). I like to think I’d still have been pleased that I asked, even if I did have to find a new shop at which to buy my important things. But perhaps that’s one for later. For now, he said yes and I’m not going to look a gift Shop Man in the mouth.

It’s important for me to note here, as I so often do, that despite writing a sex blog I am not a particularly sexy person. Not by society’s standards, at any rate. I like to think I have my own brand of charm, but society believes that women should look A Certain Way (delicate, petite, feminine, symmetrical) and if that is how you measure our attractiveness then I (nearly six foot tall, rectangle-shaped, incredibly masculine and asymmetrical in the face department) am not very visually appealing. Which makes this kind of meetcute even more exciting to me. This guy has been seeing my face (and the rest of me) once every few weeks for the best part of a year since his shop opened. He’s seen me sweaty after a bike ride, hungover after a big night out, pale and make-up-less and scruffy, and he fancies me anyway! Score! This means I won’t even feel pressure to dress up for our first date! The wins just keep on coming, and every detail of this that I dwell upon makes the rest of it shine even brighter. I don’t just congratulate myself, I do something I’ve only ever heard of people doing when God or the King is involved: I fucking rejoice.

The mission was to ask him out, and I’m over the moon that I did that. But on top of the delight that I completed such a nervewracking challenge, there’s also a thrill in the fact that he said ‘yes.’ Not only did I pluck up the courage to ask, but when I eventually did, this beautiful man told me:

“Yes, I’d love that.”

No ifs, no buts, no hesitation. He jumped in with a ‘yes’ the second I’d finished asking. I smiled back and took his number, using every ounce of spare energy in my body to prevent my hands from shaking. When that didn’t work, I tried at least to prevent myself from leaping six feet into the air, punching the ceiling and immediately pissing my knickers.

I gave him my number in return, waved goodbye, then strolled smoothly out of the shop. I didn’t even walk into a lamp post as I turned to head for home! I truly am the Queen of real-life dating.

Bow before me.


This story will, inevitably, be continued… 


  • Quinn Rhodes says:

    Aaaaah!! I’m so excited for you! Congrats on being completing the challenge AND on getting a date with a guy who seems really fun and cool. (My friends have recently been teasing me for using ‘cool’ incorrectly, so let me clarify that in this context I mean ‘doesn’t sound like a total dick and seems like he might have similar vibes to you and thus be fun to have a pint with’, or thereabouts.)

    • Girl on the net says:

      Thank you so much! And I am with you on the meaning of ‘cool’ – unless we’re talking in a ‘nice cool pint of cider after a hike’ context, I’m not sure what else cool could mean. He’s definitely a very cool person to have a pint with ;-)

  • Drew Rowan says:

    I’m beaming from ear to ear reading this, a simple, lovely girl asks boy out tale. Looking forward to the next instalment

  • What a win!! I’m super pleased you were able to ask and that he said yes. I can’t wait to hear the next instalment.
    Missy x
    PS I hope you don’t mind but you are very attractive. Ok not petite but in many other better and different ways.

  • Heavens to Murgatroyd, this is AMAZING!

    Excellent work, GOTN, most excellent.

  • Joy Asitflies says:

    I keep hearing Craig Revel Horwood saying ‘A- MAZ- ING’ like does on Strictly when someone pulls out a straight 10s samba and to be honest it fits this whole post’s general vibe so let’s go with it.

  • Jon says:

    I’m slightly disappointed that no one said FIRST in the comments.

    That’s a lovely story though. So glad that he said yes and we get to follow what happens.

  • Starcross says:

    This makes me happy! I admire your bravery – he sounds lovely. Congratulations on pushing yourself and getting the ‘yes’, he’s clearly keen!

  • Terry Bull says:

    You absolute dating legend. Appreciate how daunting and challenging this was, but you completely smashed it. Love your description, you are an amazing story teller, I could feel every ounce of your anxiety and sheer joy and achievement at the result.

  • This was brilliant to read, and it cracked me up. Can’t wait to hear about the date itself, I hope you’ll tell us. x

    • Girl on the net says:

      Oh for sure – I’ve already written part 2 and shared that with Patreons the other week, so it’ll go up on the blog at some point soon!

  • SpaceCaptainSmith says:

    Aww, well done. So… when does he get to read this blog? :) (Or has he read it already?)

    • Girl on the net says:

      Haha that might be included in a later blog ;-) But short version is that I have told him this story (though a much shorter version, ofc), but he hasn’t read this post.

  • ftandhubby says:

    That was a great read. This is the experience every man my age had when society said men had to do all the asking. Your story also reminded me of a book my wife told me young woman of her age read and lived by. It was something like “How to chase your man until he catches you”. I love that times have changed so that it’s ok for a woman to ask a man out. I’m super glad this went well for you, being rejected is never fun. Oh yea, and just know the shop guy has been waiting forever for this to happen.

  • Lawrence says:

    So this may sound naive, but I’m in earnest: is it possible for a male person to ask out a female person under similar circumstances? Without being offensive, without being… a dick?

    • Girl on the net says:

      I’m gonna throw your question back to you here, because as you can probably tell from the post, consent was something I thought a lot about before asking this guy out so I am genuinely interested in your thinking:

      Do you think that what *I* did was offensive or dickish? If yes, why? If not, why not?
      Do *you* believe that a man doing the same here would be offensive or dickish? If so, why? If not, why not?

  • TwoStrokeGuy says:

    Congratulations! As a hetero cis guy who’s supposed to do (no – expected to do) things like this, but never done and never will, I can only admire your deed.

  • Lawrence says:

    a) No, not at all! BUT, first of all it’s pretty difficult to offend me unless you are blatantly racist or Trumpist; and second of all, I’m a guy and you’re not; and being a guy comes witih the baggage of my gender and the power structure of our society. In a nutshell, men don’t feel threatened by women, and aren’t assaulted, harrassed, or worse with anything approaching the frequency that women are by men.
    b) No, I don’t at all feel like a man in your figurative shoes would be being dicking or rude in anyway. I *like* getting compliments, and being asked out is VERY complimentary. But, again, I’m a guy, so hence the question. And no, I guess I feel like, were I in your shoes, I would not feel comfortable asking an attractive girl in a shop out…. unless the unspoken dynamics were extremely palpable. Which has happened a few times in my life.

  • Not Fred says:

    OK, so I’m not Lawrence, but I’d like to chime in anyway. I think you framed the set of doubts we all have before asking someone out pretty well here:

    > Asking a man out before I’ve even had a chance to check his vital statistics (monogamous/non-monogamous; single/attached/married; straight/gay/bi; has children/wants them; religious/non-religious; lefty/centrist/right-wing-and-therefore-undateable – there are LOTS) was scary enough.

    I’d add one more question that is much more relevant to us as men than women(*), which is … has she been hit on by someone else recently? and was that dude a douchebag about it? Sadly, the answers to both of those questions are often “yes” and those of us men who are trying to be responsible and thoughtful in this space are often navigating the wreckage left behind by those who are not.

    (*) This is totally framed in a heteronormative fashion … that is just because that’s my own lived experience.

    Anyhow, props to you to for approaching Shop Man in a thoughtful and fun way. To me, it sounds like you read the room correctly and he was also interested. Hope you two have a wonderful time together!

    • Girl on the net says:

      Thank you Not Fred and Lawrence! Really appreciate your thoughtful answers, thanks! I’m going to reply properly when I get the chance to write something a bit longer because yeah this was quite a big and interesting question for me (and not one I’ve really had to navigate before) but yeah I will reply tomorrow, just a bit hectic today and didn’t want you to think I was ignoring your replies! Much appreciated!

      • Girl on the net says:

        OK so! Now I have more time to answer in detail, here goes. Firstly, Lawrence thanks for asking – I threw this question out to people on Mastodon as well because I wanted to get a bit of a feel for other people’s take on it. And got some really interesting answers (especially one from a guy who worked in retail and used to get women hitting on him a lot, in ways that made him feel trapped, which is massively ick and illustrates v neatly the situation I really wanted to avoid): Anyway, yeah do check out the replies to that if you’re interested in more perspectives.

        So for me, the short answer to your question is that I think it’s totally *possible* for a guy to approach a woman in a similar way, but I also think that I would urge caution and advise against it. I would also advise women not to copy what I did here, for a few reasons:

        1. You do not know all of the backstory, and it isn’t possible for me to give you the full context of this in a single blog post. There are things I considered/that factored in which I didn’t detail here, because what I’m doing here is giving you a snapshot of a part of my life rather than writing an advice piece on approaching that has all the relevant info included. Things you’d need to consider (which are detailed brilliantly in one of those mastodon replies) include things like the power balance between me and him (do I have power over him, i.e. financial? Is he genuinely able to say ‘no’ and risk losing me as a customer or is my custom something on which his livelihood depends?), and the power balance/relationship between him and his other colleagues (i.e. is he in a junior role and potentially gong to get in trouble if I get shirty/kick off when he says no, or is he the boss/manager of the shop who won’t feel pressured by others to treat me gently/fail to say ‘no’ if I’m being inappropriate, or does the shop have a ‘care for staff’ vibe where even if he’s not the manager, the manager would back him up if I turned bad). These are things I considered carefully, along with a few other bits and pieces like making sure that other colleagues weren’t in earshot when I asked him out, so he doesn’t have that pressure or potential embarrassment. There are other things I considered too, I’m being a bit vague due to anonymity stuff but you get the idea I hope.

        2. This ‘ask him out’ only came about because for *an entire year or more* this dude has been behaving in a fairly flirty manner with me. That’s not to say he definitely fancies me, but although I haven’t detailed all of the back and forth etc in this post, I am reasonably confident in my ability to read people, and I was pretty sure that even if this guy *didn’t* want to go out with me, it wouldn’t have been a surprise to him to learn that I might think it worth asking. There’ll be more on this in the next post, but yeah the short version is that he was very much OK with it, and extremely happy I’d asked. That isn’t to say ‘well it’s OK and consensual because he said yes to the date’ at ALL, but it is to say that I think I picked up on some signals he was giving out, and tested around the edges of those till I was as confident as I could be that an approach wouldn’t be inappropriate/creepy etc.

        3. SO! Could a man do the same? Technically yes. Technically, I have worked in service jobs before where a guy with whom I had been flirting/more friendly than I was with other customers could have considered all these questions and made an approach that was respectful, welcome and consensual. However, in my experience men who make approaches in these scenarios tend not to think about these questions in anything like enough detail. Not all men, of course, but many. Men don’t tend to have as much experience as women do of unwanted, unwelcome and pushy romantic/sexual attention, and as a result some of these things do often pass them by. This doesn’t make these men cunts, just products of a society that has given them very different experiences. What’s more, there are some proper, full-on cunts out there and their behaviour also influences how approaches might land: it is less common (not impossible, but far less common) for women to become violent or aggressive when they get turned down, whereas men do sometimes do that. As a woman, often the reason I am nervous of giving an outright ‘no’ is because hell hath no fury like a dude who’s been told no, and I’ve had a fair few experiences with that in the past. So that’s another factor as well – just something that I would ponder on if I were a man going into this situation.

        Because of these things, I wouldn’t trust the average man to make as careful a judgment about this as the average woman. But there’s a reason I’m saying ‘average’ here because there will certainly be outliers. There definitely *are* men who could do this well, and there are women who behave very badly in scenarios like this, too, and I feel like that’s important to say. There are some women who have so thoroughly internalised the (bullshit) message that men want sex at any and all times that they chat men up almost as if it’s already a done deal, and in scenarios where they have power over the guy that can be extremely harmful.

        So yeah, I don’t want to say a man *couldn’t* do this respectfully any more than I’d say women would all instinctively do this respectfully: whether an approach is respectful or dickish depends on so many different factors that are unique to the scenario. I don’t even really want to say that *I* definitely did it respectfully (though I know Shop Man would say I did, and was pleased that I did), but I do think I took many different things into account and thought very carefully about the consent of it (and mainly whether or not he was able to say no, and I would accept a no) before I went in.

        Would I advise men go out and chat up retail workers they think fancy them? No. Would I advise women do it? Also no. I don’t think I would ever feel qualified to give a ‘yes’ answer to this question unless the person asking me was an individual – a friend – who I knew well, and with whom I’d had conversations where I could probe how much they’d considered all the questions above.

  • Stephen Hammond says:

    Awwww this is such a cute story.
    And a real victory for courage in the moment, so pleased for you :)

    Having said that…
    The evil part of my brain wants to imagine you getting outside of the shop and realising that you have his number but still don’t know his name!

Leave a Reply

Your email address will not be published. Required fields are marked *

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