One Question Quiz
I am NOT inventing fake scenarios to feign outrage at. (Image: Tina Tiller)
I am NOT inventing fake scenarios to feign outrage at. (Image: Tina Tiller)

SocietyMarch 21, 2024

Help Me Hera: Dating, dating, dating

I am NOT inventing fake scenarios to feign outrage at. (Image: Tina Tiller)
I am NOT inventing fake scenarios to feign outrage at. (Image: Tina Tiller)

Your most frequently asked questions about love and dating, answered by Hera.

Want Hera’s help? Email your problem to

Every so often, someone I know asks if the letters I answer in this column are real, or whether I’m inventing fake scenarios to feign outrage at, like an under-walked Pomeranian, barking at itself in the mirror.

I can promise you the letters are real. Or at least, they seem real to me, in my capacity as inbox administrator. I’m too lazy to go around performing such subtle acts of ventriloquism. Besides, if I were going to invent letters to answer, there would be a lot more helicopter explosions, like the guy in my writing class, who responded to every short story about intergenerational trauma with the suggestion it might be more exciting if the author added in an unexpected terrorist plot. 

Having said that, I do get a lot of the same kind of letters. This is because people – or at least the sort of people who write into advice columns – have similar kinds of problems. I’ve received a couple of letters recently which have broken the 1000-word blood-brain barrier. Rather than trying to transform these Proustian epics into brief, anonymous questions, I thought I’d curate a couple of the most common problems, strip them of all context and nuance, and answer them quickly and without thinking. That is if the bomb inside this unattended suitcase doesn’t kill me and everyone else onboard this crowded passenger train first. 

QUESTION ONE: I recently broke up with someone I really liked, and I think it could be good for me to try casual dating, not only to get over my ex (which I know isn’t the right reason) but also because it’s something I’ve never tried before. The only thing I’m afraid of is hurting people in the process. How do I navigate around that?

Recently I was reading a comment thread where people were discussing whether it was ethical to be in a relationship if you weren’t over your ex. The thread was full of inexplicably married people who claimed to hold a candle for their “first love”, presumably some 22-year-old amateur skate photographer called Trent, who’s now running a successful juice franchise in Malibu. This all seems profoundly depressing to me, but perhaps I just lack emotional depth. 

I think the conventional wisdom is you should ideally be completely over someone before boldly embarking on a quest for new love. But I’ve never put much stock in the healing properties of a tasteful mourning period. In fact, I’ve often found the best remedy for heartbreak is to rush headlong into an intense infatuation with someone else. Is this psychologically healthy? Who cares. It’s much more fun than sitting around waiting for yet another wave of sepia flashbacks. 

I think it’s fine to date through heartbreak, even if you’re not sure if you’re ready. Dating is all about testing the waters and finding out. If you get involved with someone and continue to be haunted by thoughts of your ex, it’s kinder to jump ship. But I reject the idea that you have to be psychologically healthy and nostalgically unencumbered to move on. Sometimes a new fling is exactly what’s needed to sweep aside yesterday’s cobwebs. 

QUESTION TWO: I am an incredibly romantic person by nature. I have just started dating someone new and I think I’m falling for them, but I’m scared about showing my hand too early and scaring this new person before things get off the ground. Should I take things slowly, or be confident with my feelings?

I’m a big believer in the idea that if you meet the right person, it’s almost impossible to scare them off. If you have enough romantic chemistry with someone, they could spend the entire evening prank-calling the local hardware store, and it would be just as romantic as a four-course degustation menu and a ticket to the ballet. If someone is scared off by your enthusiasm, it usually doesn’t mean you were too forward, only that the feeling wasn’t mutual. 

But there’s also something to be said for taking things slow. Not because you should be wary of “showing your hand” lest you spook your new partner. Not even because it’s possible to trick someone into liking you by camouflaging your enthusiasm. But you only get to enjoy the start of a relationship once. I’d never suggest curbing spontaneous romantic gestures out of a misplaced sense of social decorum. But you should learn to eke out the nervous anticipation and uncertainty of a new love because that’s one of life’s great pleasures. 

Don’t be in a hurry to speedrun your own happiness. If things work out, you have the rest of your life to decide on the best bathroom tile grouting together. 

QUESTION THREE: Recently the person I’d been seeing for a few months broke up with me. The reasons they gave for the break-up were pretty vague and unconvincing. Can I ask for a run-down on what went wrong? Or is it better to let it go and try and move on? 

Unless you’ve been together for years, and have a strong foundation of trust and honesty, I wouldn’t usually advise seeking closure from the person who dumped you. Everyone goes into these conversations hoping to hear “I was spying for the Russians this whole time, and my handler told me I have to break up with you 😔,” but unless you’re an American scientist working at a top-secret research facility, the truth is probably only going to depress you. 

It’s often impossible to coherently explain to someone why you’re breaking up with them. Either the truth is too nebulous, too humiliating or there’s nothing to be gained by sharing it once you’ve already decided to leave. Often there is no specific reason and the break-up has more to do with a general lack of enthusiasm. 

Insisting on a forensic post-relationship rundown probably isn’t going to furnish you with inner peace. Either you’ll just get some vaguely comforting but insincere lie, a discomfiting but equally insincere lie, or you’ll end up hearing something you really wish you hadn’t (“I never liked you and was sleeping with my golf instructor this whole time”). 

It can be hard to move on when you don’t understand what happened. But even if there is a specific truth to discover, it’s unlikely that truth will help you.  Nine times out of ten, knowing someone doesn’t want to be with you is all the information you need to move on. 

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