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SocietySeptember 12, 2024

Help Me Hera: Nobody but my ex has ever asked me out. What am I doing wrong?

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I haven’t been single since I was in high school. Has romance died since then?

Help Me Hera is brought to you by Bumble, the women-first dating app that started a movement by putting women in charge when dating.

Want Hera’s help? Email your problem to helpme@thespinoff.co.nz


Dear Hera,

Last year I split up with my boyfriend who I’ve been with since high school. We were together for six years, so he’s pretty much the only guy I’ve ever dated. While I don’t want to get back together with my ex, I really miss being in a relationship, and I find myself fixating on how things were in the beginning. My last boyfriend asked me out by organising a treasure hunt in the cemetery, with two movie tickets as the last “treasure”, and it was honestly the most romantic thing anyone has ever done for me. 

I have no interest in getting back together with him (there were lots of other less romantic issues), but even though I’ve been trying to put myself out there and meet new people (on the apps and IRL) I can’t seem to get a date! There have been a few people I thought something might happen with, but things always seem to fizzle out before they get started. 

I don’t know what I’m doing wrong. My other friends all seem to have a really easy time meeting people. They get hit on in clubs and university lectures and public transport. But nobody besides my ex has ever asked me out. Even on Tinder, most of my conversations seem to lead nowhere. I’m not the world’s best flirter, but I must be doing something wrong. Is romance dead? Am I doomed to be alone forever? 

Thanks! 

Future Miss Havisham 

A line of fluorescent green card suit symbols – hearts, clubs, diamonds and spades

Dear Future Havisham,

Your ex-boyfriend set the bar extremely high. I’m glad you had the experience of being wooed in a cemetery; the quintessential teenage experience. But adult men have to be more careful in their approach. If someone in their 30s tried to ask me on a date by organising a treasure hunt in my local graveyard, I would be carefully researching their name against unsolved murders in my area. 

You ask what you’re doing wrong. But as far as I can tell, you’re not doing anything! You’re waiting patiently for the next love of your life to step into the spotlight, and produce several live doves from his armpit cavity. But if your best strategy is hanging around the wings waiting for something beautiful to happen, you may be waiting forever. 

While there’s no denying that it’s incredibly romantic to be courted by a crush, I would like to suggest a radical idea that could revolutionise your love life and restore your sense of romantic agency. 

Start asking men out. 

It’s one of my diehard relationship convictions that heterosexual dating would be better for both men and women if women were more emboldened to make the first approach. There are so many reasons for this, and I’m now going to punish you by enumerating all of them.  

Men are afraid. Not just of rejection, which is an equal opportunity misery. But men have a fresh 21st-century fear, which is not wanting to be seen as creeps or predators. Sure, some of this anxiety seems a little hyperbolic. But if I were a man, I would be scared of asking someone out, for fear of making them uncomfortable or seeming like a pervert. 

There has been a lot of discourse in the last decade about how tedious it is for women to be treated like walking rotisserie chickens. I’m not saying women shouldn’t complain. They’re describing a very real frustration. But the corollary is that men who can read the room have heard this complaint and adjusted their behaviour, and cold approaches are now less common. 

I’m not suggesting women ask men out to protect men’s feelings. As a woman, waiting to be asked out is a statistically inferior way to date, because you’re automatically going to get a higher proportion of people who don’t care about making women feel uncomfortable. Trying to choose from this limited selection pool means you’re already off to a bad start. It’s like how they tell children lost in public that it’s safer to approach a stranger and ask for help than waiting to be approached. I’m not saying men are opportunistic paedophiles and women are lost children. But you’re much less likely to accidentally proposition a pick-up artist than a pick-up artist is to proposition you. 

There are many practical reasons why being proactive is more likely to get you what you want. Asking men out means you get to set your standards high, rather than simply choosing the best available candidate. I think a lot of women would be surprised by just how high they can punch, simply by taking a little initiative. I know so many women who could have had almost anyone their hearts desired and simply ended up with the first junior property developer bold enough to buy them a pint. 

You may think this is unromantic. But being in the driver’s seat doesn’t mean you have to forfeit romance, because men like romance too! In fact, there’s nothing stopping you from going ham and organising a cemetery treasure hunt of your own. But ultimately it’s more romantic to meet someone you really like in a boring way than it is to meet someone boring in a romantic way. 

If you’ve spent your whole life with the unspoken expectation that men should do the asking, it’s going to feel a little awkward at first. But if you’re nervous about the idea of asking someone out in person, you can always practise on the apps. It’s hard to volunteer yourself for rejection, regardless of gender. But so few men ever get asked out that you can feel confident knowing that even if they’re not interested in you, they’ll probably be flattered by the attention. 

My advice is that the next time you meet someone you’re interested in, don’t let it fizzle out. Maybe it’s your turn to play Mr Rochester. Be the dashing sea captain of your own destiny. And for god’s sake, invite me to your wedding. 

Keep going!