Questions and positivity: Test date with a blog reader

Image by the brilliant Stuart F Taylor

When I posted the following offer, I didn’t expect anyone to take me up on it: “I have no Valentine’s plans so am considering lining up phone dates… I’ll date you then explain why you’re failing. Tempted?” But somebody did! A dude who genuinely wanted to get better at dating, and asked for my help to pinpoint where he might be going wrong. Here’s what happened when I had a test date with a blog reader.

Whatever you take away from this, remember that it takes a lot of courage to put yourself up for analysis in this way and that’s no small thing. The guy in question, who I’m going to call ‘Jack’ for anonymity, was polite and friendly and nerdy and nice. He made a few mistakes that I hope the rest of you can learn from, but the very act of doing that makes him a bloody good sport. For what it’s worth I think he has a lot to offer the right person, and I wish him lots of luck. Big thanks in advance to ‘Jack’.

I have a rule these days that I don’t date blog readers, but sometimes an opportunity catches me at just the right moment. When Jack popped up to ask if I was serious about doing a test date for feedback, I was in a playful mood so I figured… why not?

This isn’t just a test for him, though: it’s also one for me. I’m often bad at giving constructive feedback because I’m scared of upsetting people. If he genuinely wants useful input that will help him get dates in the future, I have to grow a spine and actually offer critique rather than just encouragement. So as well as being an experiment to check out this guy’s game, it was partly a test for me. If he made mistakes, would I be able to articulate them with clarity?

Let’s find out!

The test date: phone chat and openness

Let’s begin by acknowledging that this is a weird situation. Not only are you having a last-minute phone date with a borderline stranger, she also happens to be a professional sex blogger whose work you’ve followed for roughly four years and you know she’s going to write about what transpires for a massive audience. Not a relaxing scenario. Jack will do well if he can make it to the end of this ordeal without bursting into horrified tears. Luckily for him, I’m a truly lovely person. I’m great at making men feel at ease on dates because I’m an obsessively people-pleasing fucker who’s keen for everyone to love me.

LOVE ME.

The actual phone date goes well, let’s start there – we have a fun conversation and he genuinely opens up. We don’t just talk about our music taste, shared joys and fun hobbies (though we do and that’s lovely), we also chat about some of his challenges and insecurities when it comes to dating. As a general rule, I wouldn’t advise you launch into this on first meeting, but I asked him outright and it wasn’t a trap: I was legitimately curious about what made him take me up on my offer, and grateful to him for answering me with what felt like true vulnerability. He deserves big points for this, in my opinion. It’s hard enough to be open with a stranger, let alone one you know is actively trying to judge you. For this reason, plus anonymity, I won’t go into detail about the conversation itself. I’ll just tell you that the test date was fun, I smiled a lot and had a nice time, and there were a few things Jack could have done better – mostly in the run-up to the chat. So, as promised, constructive critique.

ASK QUESTIONS PLEASE!

Before the date, I ask Jack to send me a brief profile, and treat this as he would if we were meeting on a dating app. He sends enough info to spark conversation without giving too much away, but sadly doesn’t ask me any questions.

Maybe he just didn’t realise we’d started? I should be fair. As always, I am keen to nudge men to do the right thing so when I reply with a dating profile of my own, I prompt directly: do you have any questions you’d like to ask before you agree to a phone date with me? He replies ‘no’ and my heart sinks.

I explain that I was hoping for a little curiosity, and he immediately changes tack. Says that he thought I would care about my privacy (No, I am an obsessive oversharer! I wish to talk about myself all the time please!) and that he assumed everything I’d want to tell people was already on the blog (No I am an obsessive oversharer! I find new things to talk about every day! The blog is less than 1% of the things I wish to tell people about myself and my life!). But I see where he’s coming from: the logic is sound even though it’s wrong. Suitably prompted, he asks a bunch of questions based on GOTN, plus a couple that he’d be likely to include in a first message on a dating app.

Thank FUCK. OK. False start, but fine. My advice to him at this point – and my advice to all of you – is that you should never make assumptions like this. In our initial message exchange, Jack made more assumptions about me than he asked questions, which is fairly typical of men I’ve met on the apps. If you can flip this ratio, my dudes, you will instantly stand out from the crowd. Easiest trick in the world, I’m telling you. ASK QUESTIONS.

On the call itself, making notes for this post, I do a tally chart of how many questions each of us asks the other. Discounting the simple ones like ‘how are you?’, the count reads:

Me: 11

Him: 4

Don’t be shocked or mean to him about this. It may seem unbalanced, but it’s actually pretty decent work. The fact that his number is greater than zero puts him ahead of roughly 80% of the men I have dated, including some actual boyfriends. I include this section only because I can literally never pass up an opportunity to bang this particular drum: ASK QUESTIONS.

Try to be positive

The next piece of advice I have for Jack – and for most men in the dating pool – is to try and be positive. When he asks about my profile, here’s what he goes with:

“In terms of [music you like], I’ve only ever heard [band]. What else should I listen to?”

and

“I don’t really like [thing you mention], can we even be friends?”

I can see he’s trying to hit a ‘playful’ tone (and he confirms that he is), but playfulness with a stranger is a high-risk activity: it reads like negging. You have to make sure your playfulness is coming from a positive place and will land (with, remember, a stranger) in the manner you intend. For me, a girl who just drafted a funny, cute, vulnerable profile listing some things I love, reading Jack’s questions feels a little deflating. The only things he can find on my (detailed, expansive) profile to comment on are a) a type of music he isn’t into and b) something he doesn’t like at all. It’s almost as if he doesn’t want to date me specifically, but he wants to date someone and I’m the one who happened to show up so he’s making the best of it.

No shade to Jack here, as I say – he’s trying to be playful. But positivity is more important, infinitely so. In our pre-date messages he’s told me that he doesn’t actually get many dates – ‘messaging’ is the hurdle at which he falls. And from comments here on the blog, I understand that this is the problem many of you have too, so after ‘ask questions’, this is probably the second most important piece of advice:

Be positive.

It’s hard to put yourself out there. It’s a challenge to be vulnerable. Setting your heart on a chopping block and saying ‘this is mine, would you like it?’ is frightening. But you kinda do have to do it if you want to get a date. The person you’re messaging needs to know that you’re specifically eager for them. In a world that’s been poisoned by prize bellends who think you can neg your way into somebody’s bedroom, you can easily stand out from the crowd by being open, vulnerable and eager. Play easy to get.

If you need more guidance on how to do this, try the following formula:

Compliment, connect, question.

Compliment something on their profile, connect with them over it, then ask a question.

  • I love [name of band they have mentioned] and I saw them at a gig back in February! Amazing live act, would love to go again – possibly my gig of the year? What’s the best gig you went to last year?
  • Genuinely laughed out loud at your Monopoly joke, I’m also a bit of a board game nerd – that one’s my nemesis when there are so many better ones out there. Do you have a favourite? Any new ones I should check out?
  • That picture of you on a clifftop is iconic. I’m really into hiking too. Where was that photo taken and how long did it take you to get up there?

See what I mean? Prioritise positivity. Women on dating apps are drowning in boring spam (“Hey, how’s it going?”) and negativity (“Don’t just LIKE me, MESSAGE!”). Be the positive light that makes them smile rather than roll their eyes!

Dating should be collaborative, not competitive

While we were on the phone, and in email afterwards, Jack was very complimentary about my charm. That’s nice, and he’s correct: I’m incredibly charming. Just an absolute solid-gold, fun-as-fuck individual. I have worked pretty hard on my people-pleasing, and I’m proud of being able to carry a conversation in even the strangest dating scenarios. This is why I have a high hit rate (possibly 100%?) of conversion from first date to second. Full disclosure: in my 20s it might have been more about the quality of my suck jobs than my chat, but these days I don’t shag on date one so I know my chat is solid.

Anyway. I’m charming, that’s the headline. Jack recognises this (he’s clever) and he mentions it (he’s kind). I’m flattered, and I glow at the compliment – it makes me feel good and like we’re on a solid path. I make a note that reads ‘HE IS GENUINELY LOVELY’ and I’m excited. It’s nice to be complimented for anything, of course, but to receive praise for something I specifically and deliberately work at is where the magic happens. Thank you Jack.

However, next he tells me that my charm is ‘intimidating’, which stings.

It’s gutting to realise that something I work hard at, specifically to make men feel comfortable, actually ends up intimidating them. I carry the conversation, often uphill and with effort, because I enjoy shy guys and I know I have to do a bit of work to score one… and the fact that I do this is intimidating? Fuck! Should I just… give up completely? Perform the conversational equivalent of a human starfish?

To me, ‘intimidating’ means ‘I am afraid of you’, and I try very hard to never do anything that might make decent people feel afraid. Some men are afraid of me anyway, it turns out. The better I am, the more intimidated they are, as if dating is a competition and if one of you is charming then the other loses points.

Join me in a sad sigh here, people: I’d love to meet a man who sees my good points as his gain, and not his loss. Someone who celebrates my sparkle, thinking not ‘how does her brilliance make me look bad?’ but ‘how awesome is it that I’m dating someone so good?’. That’s a topic for another day, though. For now, just know that if someone is charming and fun, and you’re on a date with them, that’s a reflection on how cool you are, not a stick with which to beat yourself.

Style versus substance

I’ll be honest, by the time we get to the end of the test date I am struggling to locate a cast-iron reason why Jack would struggle to get a second from a first. He’s open, honest, chatty. Has some fun nerdy hobbies that he can speak about with passion. He asks questions on the call, and is genuinely trying to connect when he answers my own. I hope you have noted that none of my critique is about Jack as a person – as a person he is fab. I’m nitpicking here about his style, but I want you to know that the substance is sound. Jack’s eminently date-able, so why does he struggle to get dates?

Then after our phone call, he sends me an email, and suddenly I understand what might be the underlying issue.

 

Part 2 of the test date is live now…

20 Comments

  • Matt says:

    Would you ever consider doing this as a paid consultation? Your advice is extremely valuable, and we need all the help we can get 😋

  • Matt says:

    Would $100 an hour make it worth the effort?

    • Girl on the net says:

      Sure! It would take at least 3 hours though, and I probably wouldn’t be able to do it in as much depth as this. I would guess this took about 8 hours total for the messaging/profiles, then the actual date, then the blog posts and then the feedback call. But I could do a shorter version in 3 I reckon. Drop me an email innit – hellogirlonthenet at gmail dotcom x

  • Anagja says:

    What a cliffhanger :-)

    I think this “It’s almost as if he doesn’t want to date me specifically, but he wants to date someone and I’m the one who happened to show up so he’s making the best of it.” is very true. On every dating site I was registered, there was a definite imbalance between women and men. This is one of the consequences – if a woman sends a non-negative reply, men feel they have to grab the opportunity and hope that on the date it turns out there’s chemistry between them. It also might explain why some men don’t ask questions on dates – they don’t want to really know the women because it might turn out they don’t actually like her. Or the questions themselves might turn off their date. Sex would be OK with an almost stranger though.

    Before dating sites people usually knew each other even before the first date. They were classmates, colleagues, shared friends, etc. There was something common to start a conversion. On dating sites this is not true, people go on dates with complete strangers (there are extremely few profiles with information). It actually makes asking questions harder (well, there are exceptions, but for many people) because people don’t even know each other enough to ask questions!

    One more note about “intimidating”. I think I’d feel “intimidated” when I feel my game is not up enough. I mean “here’s this intelligent, charming woman with big boobs – why would she ever want to have a relationship with me? There are plenty of better guys than me…”

    • Girl on the net says:

      On the intimidating point, I think part 2 might be useful to you =)

      “On dating sites this is not true, people go on dates with complete strangers (there are extremely few profiles with information). It actually makes asking questions harder (well, there are exceptions, but for many people) because people don’t even know each other enough to ask questions!” This is a good point for sure, and I totally get why it’s hard – often you don’t even know which topics to ask about, especially if someone’s profile is very sparse. My approach here is that I literally never approach, message or even reply to someone who doesn’t have enough info on their profile to ask something. It baffles me how many dudes on dating sites don’t bother to fill out their profile properly but have something like ‘I’m an open book – just ask me!’ somewhere in there. Dating is not a matter of just showing up and waiting for the messages to roll in, you have to make an effort. Those who don’t make an effort with their profiles are unlikely to make an effort in a relationship. Fundamentally, a good dating site profile should prompt people to want to know more, and show off enough about you that the *right* people will want to engage. More on this here: https://www.girlonthenet.com/blog/best-online-dating-profile/

      ” It also might explain why some men don’t ask questions on dates – they don’t want to really know the women because it might turn out they don’t actually like her. ” This is SO depressing but I think you are articulating something important, and likely true in a lot of cases. The scarcity mindset in dating means that men are often on the back foot when a woman contacts them/replies. She’s precious purely because of her scarcity, so dudes are disincentivised from doing anything that might either scare her away or reveal things about her that they don’t like. BUT this is not a helpful mindset if you want to find someone you genuinely connect with – it’s just wasting everyone’s time and let’s say you do end up in a relationship with someone you don’t know or don’t like much… what a horrible outcome. Better to not end up with anyone at all than end up in a relationship that’s wildly inappropriate for you. What’s more, *behaving* in a way that comes from this scarcity mindset is (perhaps counterintuitively) going to hamper you in finding dates in the first place – being broad, vague, disengaged… all these are turn-offs to most people. There’s a bit more on this in the post here under ‘scarcity mindset’ heading: https://www.girlonthenet.com/blog/emotional-honesty-faith-in-dating/

  • Kate says:

    Thank you for writing this. I continue to be baffled by the number of men who not only ask me zero questions in online dating messages but also ask me zero (or nearly zero) questions on dates. I would NEVER agree to go on a date with someone I didn’t have some curiosity about, as there would be no point in going on a date with them in that case – so when a man doesn’t ask me anything, I assume he has no interest in me, which means I’m then tasked with the laborious, thankless task of single-handedly running a conversation with someone who seems to find me dreadfully boring. Not my idea of a fun night, unfortunately, and CERTAINLY not the type of night that leaves me feeling attracted to someone and eager to get them into bed. If I had to work that hard to make the conversation work, I assume the sex will be even more exhausting and unenjoyable.

    • Girl on the net says:

      Absolutely! And thank you for sharing and commenting. I’m baffled by how many people fail to do this, when it seems so easy and is something many of us have been saying for a long time.

  • Raven Stromdans says:

    I hate that everything new I learn about how dating works these days convinces me I will never so much as a get a date, much less find a relationship ever again.

  • Raven Stromdans says:

    I’ve actually been thinking that over, between absorbing this post and Dr. Nerdlove’s response to a similar expression of frustration I left on his link to this article on Bluesky – and I think it comes down to the fact that if I found myself trying to focus on all the things that I learned from years of reading his posts and what I’m picking up from this article, I’d never be able to actually interact with another person at the same time.

    I’d be so focused on trying to deploy all this stuff I learned that was supposed to help me, I can’t imagine having anything that approached an authentic, organic interaction with another human being period, much less one I was trying to get to know well enough to find out if I wanted to date them/they wanted to date me.

    I feel as though all of this is more likely to get in the way rather than help. But I’ll be honest, it’s all a moot point anyway…as lonesome and lovelorn as I am, I don’t have it in me anymore to accost someone else with my presence in the hopes of making a connection.

    • Girl on the net says:

      “I feel as though all of this is more likely to get in the way rather than help” – so then I guess the obvious next question is… why read it? You say you follow Doctor Nerdlove’s work, and I massively rate his advice. Although, sure, it’s probably not going to be possible to remember every single specific piece of advice, not every single specific piece of advice is going to be relevant to all your situations. The key is that his advice is all based on consistent foundations: have respect for others, be willing to put the time in to unpack your own issues, etc. Many people find it extremely helpful – and I got a lot of good response to this piece from people who said it helped them. And the commenter on BlueSky who pointed out that this isn’t magic ‘catching girls’ advice, it’s just basic ‘interacting in a fun, curious, kind way with *people*’ advice, so you can practice doing it in any interaction – not necessarily just dating ones: I think that’s worth remembering too.

      If it doesn’t work for you, that’s OK: this is a big wide world and we’re all different.

      But what I find weird about your comment (here and on BlueSky) is… you’re still reading? You’re saying this is of no use to you, in fact actively hindering you, yet you’re still reading, and then you think that it’s appropriate to leave comments which essentially amount to telling me (and an experienced advice blogger whose work has helped countless people) to just stop doing it. Off the back of your own individual experience/desires/needs. But you – YOU – have control over your life and the media you consume. Do you know you can just stop reading things that you don’t like? Why then take the next step and demand we stop writing for anyone else either? Why do you believe that the world should be remade around you, just because it isn’t currently dispensing what you have decided you specifically need? You don’t have to consume dating advice if you think it’s unhelpful to you, but what you’ve done here is the equivalent of walking into a steak restaurant and loudly declaring that you’re vegetarian so the restaurant should shut down. Why?

  • Raven Stromdans says:

    I will try to be brief and concise, otherwise this is going to come across as an unpaid therapy session.

    1. I never told you to stop doing what you do and frankly I don’t know where you got that from what I wrote. You’re helping people and that’s fantastic. Whether it works for *me* is immaterial to that fact; I was specifically commenting on whether I thought it could work for me and my frustration that I felt it wouldn’t. No approach, no advice, no suggestions are going to work for everyone, but as long as they’re helping *someone*, that’s what’s important.

    2. I return to this kind of content intermittently, mostly in the hopes that I’ll encounter something that will get me past the deeply insular and lonely life I’m currently stuck in, knowing full well that I’d have to make way more radical changes in my life to be able to even deploy the dating and relationship advice I’ve absorbed over the years…and I know that’s not going happen.

    3. I apologize if it seemed as though I was lashing out at you or unfairly criticizing your advice. I’m sure it’s perfectly cogent advice, especially with the recommendation of Harris I would expect no less. I let my frustration of diving back in to look for something new that would help me only to find more tools I’ve no capacity to use get the better of me.

    I am curious to see the second part of this particular journey…I rather think I’ll keep my thoughts on its resolution to myself this time.

    Good journey.

    • Girl on the net says:

      It’s more that you chose to comment and say ‘this is unhelpful’, so OK no you’re not technically saying ‘stop’ but you’re being negative in ways that can be really demoralising. I get that not everything is going to be helpful for everyone, but that kind of negativity grinds me down. I get it often from men on dating advice pieces, where they go ‘well, this won’t work for me for XYZ reasons’ and I’m like ‘OK, but all I can do is my best’ – the act of commenting to say ‘this is unhelpful’ carries an implication that I’m doing something wrong, or at least like I should be doing something *else* and I don’t always know what that is. Even on pieces where I talk about shagging guys I met on dating sites, I get comments from men saying ‘this is depressing, would never happen to me’ and I’m like ‘OK, but… I can’t come and individually shag everyone from the comments, can I?’. I can and do try to talk positively about what I think would help dudes, and it is very very rare for me not to receive a comment like yours. There is always someone who wants to tell me that my help/advice/stories are unhelpful. It’s one thing feeling it then not reading further, it’s another to actually say it to me directly – I don’t know what I am expected to do with that.

      I appreciate the apology, thank you, and I hope you find this explanation, and part 2, helpful. I genuinely think it should be, and I also genuinely think that dating as it stands is not a particularly positive or happy place for many of us. Best of luck on your path.

  • A Llama says:

    > “My approach here is that I literally never approach, message or even reply to someone who doesn’t have enough info on their profile to ask something.“

    This is 95 percent of my Feeld stack, at the times when I haven’t exhausted the profiles of the three people in said stack. It’s fortunate that you have other outlets to meet and fuck people and get to make that decision. I don’t, for a number of reasons. I wish I did. I would like to a lot, especially right now when I’m the most open to it. There’s a lot I can give to people, but they don’t want it.

    FWIW, my standards are that I don’t engage with zero content profiles either because I always take care with mine. Sometimes, I have had to compromise and maybe message low effort ones if the distance, age, pics, and tags are within my range. I say this like I’m going through 50 profiles a day and getting a ten percent match rate. It’s not. Most of the time, I’m at the end of the queue until another profile decides to pop up.

    I ask a lot of questions. I’m sociable and have no trouble asking someone out. I’m interested in people and want to get to know them and I am literally giving them the best chance to be a sexy bastard with me. It’s not been reciprocated though.

    This was me shouting into the void really to cough up my viewpoint. I’m both looking forward to and dreading the part two.

  • Willow says:

    Lots of good stuff in this article, but I found your section about the “intimidating” comment interesting and a perspective I hadn’t considered before.

    Is it really that much of a faux pas? For me, being intimidating is actually an attractive quality, and most of the women I’ve had crushes on or caught feelings for are people I found at least somewhat intimidating. They usually had a ton of cool stuff going on, didn’t take shit from others, and were super strong-willed and smart.

    As a guy who really wants to date but hasn’t gotten the chance at all yet, I also find the whole process “intimidating” in the first place. In my mind, the ideal date would be, yeah, someone who’s a bit intimidating, prone to push my buttons, and may put the fear of god in me from time to time, but also is balancing that with expressing interest in me and making me feel seen.

    I don’t know and maybe it’s the inexperience talking, but to me it’s like a good horror or thriller movie. It’s not scaring you *away*, you’re still glued to your seat and your attention is drawn in even further.

    I feel like I could fall into that same situation you mentioned with someone taking that word as a negative from me. Would you react any better to someone saying “you’re intimidating, but in a good way”, “you’re intimidating, but I like being in the hot seat from time to time”, “you’re intimidating, like most good things” or a similar reframing? Would it be better to chuck the word away entirely and instead opt for directly complimenting assertiveness or other similar qualities?

    (As a last aside- it’s reassuring to see so much advice boil down to “ask questions” and “show genuine interest”. I feel like I’m really good at that side of things and could do well on a date, I just haven’t had any luck getting to the “first date” stage in the first place.)

    • Girl on the net says:

      I could write so much on this, but I’ll try and keep it short. Laying aside the fact that dating is intimidating (it is and I think that’s a completely legit thing to say – the process is intimidating for many of us!), I don’t have any issue with anyone saying that. I want to look specifically at the issue of telling a woman she’s ‘intimidating’.

      Let’s start by asking… would you use the word ‘intimidating’ if you were talking to a man? Would you call a dude ‘intimidating’ if he didn’t take any shit and was strong-willed and smart? If not, why not? Just have a think on that for a second before asking yourself the next question…

      What do you hope to achieve by telling a woman she’s ‘intimidating’?

      The problem is we live in a patriarchal society that expects men and women to be a certain way. Men should be strong, competent, smart, funny. Women should be soft, quiet, gentle, calm. We are told so often that our purpose and role in life is to be the supportive person standing next to (or behind) a man, being quieter and smaller than him. But many of us are not like that – we do not wish to be like that. And it takes quite a lot of work to kick back against these societal expectations and say ‘actually, I am comfortable in my own smart, strong-willed skin thanks very much’. I imagine there is a similar kind of courage required to be a man who doesn’t conform to gendered expectations of men (tall, strong, opinionated, etc) but let’s focus on women for now.

      It takes work to carve out a space for ourselves in this world, and often we have to tiptoe around the feelings of men in order to do it (be strong but not TOO strong) in case we are rudely or sometimes even violently put in our place. I wrote a thing that is partly about this a while ago – https://www.girlonthenet.com/blog/a-man-who-loves-strong-women/ There are lots of men who enjoy/adore/*fetishise* strong women while they’re hoping to catch us, but ultimately what they want is not to date us and bask in our glory, they want to *tame* us, and get angry with us when we don’t turn into soft/small/quiet women when we’re by their side. Confident women have to navigate this often, and we usually do that by adopting a level of people-pleasing to go along with our confidence. A spoonful of sugar to help the intimidating strength go down. A kind of apologetic ‘yes I am smart but look at me using my smarts to help you feel comfortable’ – which I think is broadly what I do on dates. I am not rude to men, or cruel, or cutting. I don’t do things that would harm them. I am very careful with my compliments, and wouldn’t ever give a guy a backhanded one that actually made him feel small while purporting to be positive. And yet men call me intimidating anyway. I am kind, funny, welcoming, caring, interested in them… I do not shout at them or say mean things as so many men have done to me. So… why is this stuff intimidating?

      At this point… there is not much else I can do to prevent them from being intimidated other than just to shut up. And that is *agony*. Which is why I ask… what do you hope to achieve by telling a woman she’s ‘intimidating’? Because most of the time the effect of comments like this is to grind us down and essentially nudge us back into a box (small, quiet, calm) rather than encourage us to be more ourselves – more confident, strong, etc. You’re welcome to think ‘wow I am a bit intimidated by how awesome this woman is!’ but the second you say it aloud you’re giving her something that she has to deal with. And yeah, maybe some women will take it as a compliment, but I suspect that most women like me will – because of our experience over many years of men using backhanded ‘compliments’ like this as a way of putting us in our place – take it to mean ‘sssh now. Be smaller and quieter because I am feeling insecure and that is your fault.’ Honestly. If a man is intimidated by me, I’d suggest that’s a problem for him to solve and not one for him to throw into my lap.

      I don’t think most men do this consciously or deliberately (though I’m sure some do), but enough of them do it that it has a cumulative effect that is, honestly, extremely demoralising and counter to a lot of the things I am working very hard to learn in therapy. So. I get your point that you find it attractive when women are intimidating (maybe). But I want to end by asking you to consider what the point is of a compliment. Your comment is nudging towards ‘can’t you just take it as a compliment?’ territory, but I think if you want to compliment somebody, the onus is on you to make what you’re saying actually *nice*, rather than loaded with expectation and insecurity. Tl;dr – ‘intimidating’ is not and never will be a compliment to me. If you think I’m smart, say ‘smart’. If you think I’m confident, say so. If you think I’m strong, say that. But ‘intimidating’ adds a value judgment which – especially in the context of a patriarchal society – lands as critique, not compliment.

  • Datelessman says:

    This was an enlightening article. Both of you were pretty brave to do this and it offers some great advice. Thanks for sharing it!

  • Willow says:

    Thank you so much for the reply! I think I better grasp what you’re getting at and understand how saying that to someone could be a vibe killer or even hurtful. You ask the point of me saying it as a compliment, and I’d say my intention would be for the other person to keep on being themself around me and *not* have to tone themselves down. But yeah, with how you walked me through it I see it’s much, much more likely to do the opposite. Thankfully I’ve kept the notion of using it as a compliment in my head up til now so hey- you probably saved me a blunder in the future!

    Your linked post as well was also pretty revealing- that’s the opposite of how I want to be whoever I’m with, so I’ll keep reflecting on how to avoid any snags or see warning signs in the future that I might fall into that trap. (I imagine it largely has to do with avoiding insecurity and self-loathing, which your part 2 talks about super well!) Thanks again!

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