Girl on the Net

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 coming soon… subscribe for updates.