There's the time and money it takes to style your hair and apply a fresh face of make-up, and even pick up a new outfit if you feel so inclined: but there's also the worry most women have when meeting a date for the first time.
Is he going to be the smart, funny, kind guy he seems to be in his online dating profile?
Or is he going to be the opposite: inconsiderate, rude, or even downright creepy?
"Sometimes, the woman has to be the braver of the two of you just by being there," Tom said.
While he's certainly had a few mediocre dates, he hasn't had an experience that he considers to be truly terrible.
I — and quite a lot of his female friends — haven't been so lucky.
"To offset that, I think it's only fair that the guy pays for dinner. You don't have to be loud about it; it's just a little acknowledgment that you're grateful she came."
Whether you agree with Tom or not, he must have been doing something right: after all, he's happily married now.
But as I remain single, and actively dating, I find myself pausing as I reach for my purse at the end of each evening: should I offer to pay for us both? To fairly split the bill? Or to see if my date, like Tom, is going to call the evening his treat?
Historically, the tradition of the man paying for everything on a date was born out of the fact that women rarely had the financial resources to do so.
If a woman was prevented from working due to her gender, or paid very little for whatever job she was able to do, it seemed only fair that the man — who may have been earning much, much more than she was able to — would pick up the tab for the time they spent together.
But that was a long time ago.
When I look around at my circle of female friends, we're all successful, financially-stable people.
Even in Sydney, where the highest of salaries can still see you struggling to top up your Opal card and pay your rent in the same week, we somehow manage to get by: sometimes even earning more than the men we're dating.
As much as a gesture like Tom's is appreciated — because we all have a story about meeting a date who put us on edge — should we expect, or even allow, men to put their best financial foot forward in the name of gender politics?
When I first started dating it felt sweet and innocent to pool my cash with a crush and see what we could make out of our limited resources: grabbing the cheapest bottle of wine on the shelf and splitting it over a greasy bag of fish n' chips in a park was charming, not cringey. But I'm thirty now, and I'm not afraid to say that my standards have changed.
These days my ideal first date involves conversation over dinner and a martini or two, rather than bumping elbows at a local pub as we try to shout to each other over the noise of our local two-for-one happy hour.
So I'll freely admit that maybe I'm not the best person to explore a list of 'Sydney's Cheapest Date Ideas' with, but along with the knowledge that my tastes have changed as I've gotten older comes the understanding that if I want to keep my standards high, I need to be prepared to cough up some cash.
If I'm on a date with a lawyer who's hinting at a salary in the upper-six-figures while describing his corner office above Martin Place, then certainly I won't feel hesitation if he whips out a platinum card when the bill arrives.
But if I'm having dinner with someone who's between jobs, or working on a passion project while scraping by with a minimum-wage gig, I'd feel guilty expecting them to pay the both of us.
After all, shouldn't I be the only one who has to be responsible for my expensive cocktail choices?
In an ideal world, perhaps all men would be shouting women dinner and drinks to atone for the sins of others: but then again, in an ideal world, nobody would have to feel afraid to go on a date to begin with.
If a date has made it past the initial greeting stage, and hasn't found himself on the receiving end of a polite but urgent reason that I need to leave immediately; there's a high chance he hasn't set off any blaring alarms on my creep-o-meter and I'm comfortable enough to spend the next few hours with him. While it feels impolite to refuse if a date is particularly insistent that he pay; it's surely equally as rude to sit across the table and expect the bill to be taken care of for you.
Of course, I can't speak for others. I've heard a litany of stories from friends who swear that they would never allow a woman to pay for a single thing on a date, while others prefer the bill to be split equally.
A very small number of people I know have relayed stories in which the woman has offered to pay for everything, and they've agreed; accepting it as a small payment ahead of a relationship in which they imagine themselves outlaying more and more money to keep their partner entertained.
What can I say? When it comes to dating, it seems there truly is no such thing as a free lunch.
— Kate Iselin is a writer and sex worker. Continue the conversation on Twitter @kateiselin
