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How to let someone down easy after a first date 

IMAGE VIA @CLUBSUP_/INSTAGRAM
WORDS BY GENEVIEVE PHELAN

“Even though it’s uncomfortable to execute, the termination message must be sent.”

I am the person that leaves most first dates feeling disenchanted. When I get that ‘idk’ feeling (you might know the one), it’s often just denial. It means I didn’t really enjoy myself and don’t want to see them again, but that is occasionally too frustrating to process.

I talk myself (or let my mother/friends talk me) into “giving them a chance, Gen”. I feel guilt-wracked and disappointed leaving failed first dates, especially when I am accruing a compendium of them. This year’s been the worst in terms of the number of dates that have eventuated to anything. Probably something to do with our perpetual hermitude.


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There have now been two lockdown eves ensuing in cancelled first date plans that were scheduled for the weekend. (Is a disclaimer even necessary here to say I am aware much bigger issues are at hand than my dating life?). As I write this, I sit waiting for the fate of a hypothesised ‘walking date’ in lieu of the original Sunday dinner we had pencilled in. Of course, no solidified plans have been made and I sit here finding solace in reflecting on dates past to reconcile my disappointment with another COVID-cancelled one

There has been a vast spectrum of meet-cutes over the last couple of years. There have been iconic encounters, like the man I met in Cronulla three nights before ending my internship in Sydney and having to return to Melbourne. Dramatic, spicy and serendipitous, we turned a seaside dinner into a night of bar-hopping and brunch on the foreshore the next morning. On the eve of my flight home, we got gelato and sat in his beat-up Barina at a lookout point to plot our reunion. 

Then there was the Worst Date of All Time with an infamous Australian businesswoman’s son at College Lawn Hotel in 2019. After arriving half an hour late despite living around the corner, the date proceeded to order two voddy lime and sodas (nice) plus a singular parma (for himself). “This is fine, give it a chance,” I lectured internally.

But then, as his desired net worth and five-year plan were revealed (while I was not even asked about so much as my favourite colour), hope dissipated. As I sat there nursing a vodka soda lime without an offer of a singular beer-battered chip, an escape route became clear. Leg it to the bathroom, tee up friends, run away into the night to drown my sorrows. 

This year, between house arrests, I have been on a total of four official first dates. None have succeeded. Actually, none have gone to a second round. I am saying this with no pride or ego, and promise I’ve been let down very ungently in the past. But it’s been pretty dismal to get excited multiple times ’round, just to be met with anxiety and lukewarm dread the following morning.

This is when they might message you to gauge the likelihood of a second rendezvous, but you might have absolutely no interest in seeing them ever again. Sometimes, guilt, desperation and the temptation to ‘settle’ can blur your internal instant date replay for a minute. But even though it’s uncomfortable to execute, the termination message must be sent. I am driven by gut instinct and spark detection. If there’s nothing there, I’ll know in the first five minutes. See below.

Hinge Case Study

Context: This was a spontaneous first date in late June this year (see my ‘floating rock theory’ piece for reference), booked on a Wednesday for the forthcoming Friday. We went to a chic Northside pub (sounds oxymoronic, but trust me). After a good dinner, a split bottle of pinot and a lack of banter, we exited the venue.

Street-side, Date A asked if I would like to come back to his place for a wine “and a movie or something” to which I said, “I promised I’d meet my friends at a gig, but thank you”. It was a nice night but surely that’s all it was and the feeling was mutually felt. Or so I thought…

His message: “Would you want to catch up again?”

My message: “Was really lovely to meet you but I don’t think I am feeling it on that level, thanks again for dinner x.”

Some may read this exchange and think I was a savage. But as one girlfriend pointed out over coffee the other day, “the male ego is fragile” and thus I am still trying to perfect the let-them-down-easy message without being met with a passive-aggressive reply or no reply at all.

The next night I was out with two girlfriends in Richmond, only to encounter the let-down date (who had seen-ed my message) as soon as I stepped foot into the bar. Unlucky timing. I was completely ignored and that’s fine, but it got me thinking about the execution of a let-them-down message. 

If someone doesn’t feel ‘it’, what is the point of pretence? You’d embark on a second date feeling more anxious than the first, almost dreading the encounter and wishing you could click your fingers to be teleported to your girlfriend’s knockoff drinks. If you didn’t enjoy yourself and you’d rather have been somewhere else with someone else, it’s quite clear that neither party should go on to waste each other’s time. That’s just being selfish for the sake of self-preservation and a fear of hurting feelings. (I am very scared of hurting feelings.)

In saying that, the aforementioned first date was by no means a waste of time. While it can feel confidence-eroding or hope-dwindling to go on unsuccessful dates, the fact that you put yourself out there and took a chance is what life’s all about. Giving something a go, meeting someone new, trying a new restaurant and hearing someone’s stories is good for you. 

A lot of us would agree that first dates only give you a glimpse of the person you’re sitting across from. It’s merely scratching the surface. How can we possibly grasp the nuances and quirks and good and bad bits of someone from a two-hour dinner exchange in a noisy, dark pub? However, I will absolutely argue that if you didn’t laugh, get some sort of gut feeling or genuinely enjoy yourself, it’s not worth a second meeting. 

There are a few things I think we should all consider before making the decision to ‘let them down easy’. 

  1. What would you appreciate and respect to receive if roles were reversed?
  2. Is there a likelihood of seeing this person ‘around’ again soon, or do you have a mutual friend that tethers them to you in some way? 
  3. What impression would you like to leave on them? 
  4. Consider the fragility of the ego when being rejected. Some take it worse than others, but despite what you did or did not feel on that date, they could be raving to their mates about you right now. Be gentle, direct and honest. 
  5. Keep it lighthearted, concise and to the point. Nobody needs to read a patronising essay on why you cannot pursue them. 

Genevieve Phelan is Fashion Journal’s Lifestyle & Careers Columnist. Her writing fuses introspection with investigation, calling on her own personal anecdotes and the advice of admired experts in the realms of intimacy, money, friendship, careers and love. You can find her here and here.

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