How to Lose a Guy in Five Dates

How to Lose a Guy in Five Dates

As someone who’s been called a serial monogamist, I recently had the novel (dis)pleasure of re-entering the Dunedin dating scene. Now, “dating scene” is a somewhat generous term for what awaits singles on the damp streets of Dunners, which I was reminded of upon redownloading Tinder and being hit with pics of men with Big Fish, toting lewd pick-up lines asking what I’m “up to tonight haha x”. And as winter approaches, breathas are becoming even more brazen in their attempts to spend the night in a bed that isn’t on the floor and has more than a flimsy, unwashed sheet on it. And I was here to help.

We are all familiar with Dunedin hook-up culture. But how many of us have ventured outside of the Tinder, Snapchat, and root pipeline? When was the last time you went on, say, a date? Dressing up, going out, getting to know one another, maybe a cheeky bevvy or two. The whole shebang. With nothing better to do, apparently, I set out to unearth the romance of Dunedin - by going on a bunch of dates with random men. For the plot. This is going to be pretty heteronormative, by the way. But you can’t say heteronormative without almost saying “no more”, and that’s the real lesson here.

With no immediate romantic prospects waiting in the wings to take me out, I resorted to dating apps to find willing subjects. And what girl wouldn’t be tempted to cosplay as Andy Anderson? Unfortunately, Tinder and Hinge didn’t yield a Matthew McConaughey look-alike to sweep me off my feet. One guy even responded to my dinner proposal with a prompt, “No can do sorry. I’m a pump and dump kinda guy.” At least he was honest?

The following list of dates were carefully selected to allow for a variety of activities, both because I didn’t feel like forking out for six meals out in a row (my fingers weren’t crossed for these gentlemen to pay for me) and to get a feel for everything our fine city has to offer in terms of romance.

James: Etrusco at the Savoy

The Italian restaurant Etrusco at the Savoy is a little on the fancier side of the dating spectrum. A yassified BYO, if you will, with corkage standing at a cringe-worthy $9. Perhaps one to save for a Thursday night once the cozzie lives payments have replenished your bank account.

To get the ball rolling, I took my flatmate James* out for the first date. As a self-proclaimed date protegee (he takes girls on coffee dates “as a hobby”) James’ role in this was to prep me with the skills I needed heading into my intrepid journey. Like Rachel and Joey in that one episode (I watch a lot of Friends), we dressed up nice, armed ourselves with a $16 bottle of red, and walked to the restaurant together from our flat.

The popularity of the restaurant proved both a good and a bad thing: the buzz of chatter and laughter that welcomed us created a nice atmosphere, but the press of bodies meant it was stinking. Fucking. Hot. Beads of sweat immediately sprouted on my forehead, and if this had been a legit first date I would have been rushing to the bathroom to dab that shit. Instead, I settled for making fun of James' long-sleeved, wintery outfit compared to my positively summery strappy dress.

Looking around, the place screamed “date” with warm lighting, fancy decor, and intimate two-person tables dotted around the periphery. Class.

In a meta kind of way, asking James advice on what constitutes as good first date chat made for a great conversation starter to use with a prospective beezy. His advice was mainly just to a lot of questions that wouldn’t necessarily be answered by a simple “yes” or “no”, with a healthy amount of eye contact. I questioned his skills, however, when he asked me how many rabid kindergartners I thought I could take down with a baseball bat before they downed me.

Hot tips based on this date are not to bring up your ex (let alone show photos) and eat slowly if you want the date to last. Or, in the case that you contract the ick, just straight up ask for a doggy bag to take your yummy pasta home and pat yourself on the back for being so brave. Another tip: reserve talking about the method of milking whale sperm or harvesting caviar for once you’ve established a solid back and forth. And don’t tell your date you vomit-burped from red wine.

Amount of shots needed before a second date: None xx

 Tom: Poolhouse Cafe & Bar

In theory, the Poolhouse on Filleul St has everything you need to make for a great first date. Reasonably priced drinks, dim mood lighting, music, and the opportunity to strike up some cheeky competitive banter. With pool, there’s also the option to let your date pull the cliche move of showing you how to hold the stick right. The pool cue. Mind out of the gutter, please.

The man of the night was Tom*, who I’d matched with on Tinder the week prior. The details of the date are admittedly a little hazy since I was coming in hot from a Critic BYO where they’d coined my drink repeatedly and then sent me on my merry way. Sabotage!

At the bar, Tom was a perfect gentleman and paid for the table we’d be situated at over the course of the evening. Tick. He also bought me a drink which I sipped gingerly only out of courtesy. This could differ from person to person, but I quickly discovered that I am far too competitive (especially sloshed) for this to be a good first date activity. My attention belonged almost solely to the task at hand. We tied 1-1. The Knox billiards table from my first year (up the dove) proved to be good for something other than an opportunity for the wanky second-year boys to show off, I suppose.

After a debrief with the flatmates, we agreed that the best course of action with a place like this is to break the ice with a sit-down drink before cracking into some one-on-one pole action. The fact that the game involves so much focus and circling a table on opposite sides can take away from the purpose of a date, which is first and foremost to get to know one another. This could be a location better suited for a second or third date - which I also did. She’s committed.

Amount of shots needed before a second date: 5

Dylan: A Walk on the Beach

The original plan for this date was to get a Sunday morning coffee at Long Dog Cafe with Hinge man Dylan*, followed by the potential for a little beach walk if things went well. Based on his profile, which included beachy pics and surf chat, he seemed like the kind of guy who would suit the locale. Neither of us, however, had the wherewithal to check if the cafe would be open on Easter Sunday. It was not. We improvised with a wee walk around the corner and a sit down yarn on a St Clair beachside bench.

In all honesty, a walk is probably one of the best ways to spend a first date. It’s cost-effective (free) and conversation flows when you’re side by side and don’t have to worry about which of their eyes to keep eye contact with. Ours was fairly short; he started to show me the hidden path going up the cliff even further around the coast from St Clair but, after having to save me repeatedly from being blown off the edge from strong gusts of wind, we agreed it would be best to turn back.

I was initially put off a little by the fact that Dylan wore the exact cologne as an ex of mine I prefer not to think about, had a similar style of dress, and took me down the same path I’d gone with said ex three years ago. The bench yarn saved him, though, where not only did I learn that we had mutual friends, but that he had been competing in a long weekend surfing competition and my friends and I were welcome to come to the prize-giving afterparty (slay). The only downer to this date, other than the cologne debacle, was the fact that I was absolutely starving after spending two hours with this boy during the time I’d hoped to be getting a Long Dog feed (not slay).

Amount of shots needed before a second date: 2 (for confidence)

Josh: The Bog

Planning my romantic journey around Dunedin, I couldn’t overlook The Bog. A fine establishment and I will hear nothing on the contrary. The original plan had been to go to the Monday quiz night, but I was once again thwarted by the Easter weekend. If Catholic school taught me anything, it’s that Jesus is a cock-block.

My host was Hinge boy Josh*. He initially wanted to take me to the Esplanade at St Clair, but couldn’t resist my sultry counter offer of getting some Irish pub grub. Josh had offered to pick me up from my flat (chivalry isn’t dead, it seems) but Mum taught me ‘stranger danger’ and I wasn’t about to let this man know where I lived before I’d even met him. Post-date rides (wink) are up to your discretion.

At the pub, I managed to impress my date with the minimal beer knowledge I acquired through working hospo and what I’ve managed to pick up from my father’s passionate spiels about stout. It was a short date, however, since he practically inhaled his food. Maybe he got bored after I asked him whether he preferred Watties or Heinz tomato sauce. And maybe he should reflect on the dry chat that led me to that point: chat so dry that it could really use some sauce to go with it, which brings me right back to the question at hand. See?

All in all, The Bog wasn’t a bad place to be on a Tuesday evening with a cute boy. Josh was a good few years older than me and had a full-time job, so I was more than willing to let him pay for the date. And drive me home. Unfortunately, I was forced to put an end to our night of romance when he laughed at the fact that I love Taylor Swift. Misogyny.

Amount of shots needed before a second date: 4 (+2 for being an anti-Swiftie)

Oscar: Ice Skating

Turns out it can be pretty tiring being such a player - plus, I was clearly running out of original date conversation - so I enlisted the help of another friend, Oscar*, to go to the ice rink with me for my final date. If you haven’t been to the ice rink before, go. Date or otherwise, it’s a must-do Dunedin experience. An American friend of mine chose to study in Dunedin based on the prestige of the ice rink alone. I’m not even kidding.

While there’s obviously nothing sexier than watching a man struggle into skating booties and then dry-land-shuffle to the rink, the true merit of this date activity lies in its test of character. Struggling to stay upright and he leaves you in the dust? Chad. Gets defensive and emasculated after performing a one-man-show of Bambi on ice? Also Chad, and you’ll thank your lucky stars you found out on the first date rather than after a couple of months of being gaslit.

In our case, Oscar was holding on for dear life to our buddy Ruby (the ice equivalent of a walking frame). We bonded over pushing each other on Ruby, collecting snowballs from the shredded ice to throw at each other, and laughing at the twelvies face-planting around us - some of whom also appeared to be on dates. Young love. Shouting at each other over the screaming of even younger kids, Oscar and I agreed that, if nothing else, at the very least you’ll get some excitement from the dizziness of skating around in endless circles.

Amount of shots needed before a second date: 1 (it’s more fun)

Conclusion

Rather than resulting in any epic rom-com moments of love professions, my romantic journey in the end served as more of an opportunity to practise how to friendzone a guy. My advice at the end of the day would be to extend the upper limit of your chosen dating app’s age bracket if cozzie lives are stretched a bit thin and you’re in the mood for a complimentary dinner. And much like the ending of How to Lose a Guy in Ten Days, it tends not to go down all too well once your date discovers that there was an ulterior motive behind your evening outside of the wit of their Tinder bio.

*Names changed.

This article first appeared in Issue 9, 2023.
Posted 3:26pm Sunday 30th April 2023 by Nina Brown.