What Happened When I Went On 20 Dates In One Night

I’d only been on one date for the last six months before this.

By SheSaid — Last updated on Oct 23, 2022

Photo: Nejron Photo / Shutterstock

Let me just come right out and say it. Online dating sites and apps like Tinder are a collective dumpster fire that no amount of water will ever be able to put out. The focus on judging people’s looks, the insults if you don’t immediately want to drop your panties after one sentence, the carousel of unsolicited 'd' pics ... the list goes on.

So when an ad for speed dating popped up in my Facebook feed, I paused.

Past Liz would have scrolled on by, but at present Liz was so broken down by modern dating advice and trying to figure out how to find true love that she thought, “Why the heck not?” Surely it couldn’t get any worse than someone calling you fat because you took too long to text back.

I mean, when you compare it to delightful interactions such as that, speed dating has to be a better way to meet new people than online dating right? Right?!

And it was — on that night. But afterward? I’m pretty sure it crushed me more than any online dating stint.

Speed dating, with a twist

One of the main reasons this particular speed dating event piqued my interest was the way it was structured. In order to gain automatic entry, all speed daters had to bring a single friend of the opposite sex that they vouched for.

Now, this might not seem so revolutionary, but I’ve heard stories that make this little format tweak super enticing. Stories like how certain male friends of mine, even while already coupled up, have been asked to attend speed dating nights to both make up the numbers, and to flirt with the women to make sure they feel like they’re getting their money’s worth. Which is just gross.

I figured this idea of bringing along a friend you think is awesome but just not for you would, theoretically lower the douche quotient in the room at the same time as making sure there were equal numbers of men and women, negating the need for decoy ring-ins.

Theoretically.

Before the event, I was super excited. I’d get to meet a bunch of eligible bachelors, have chats in person instead of via text, and maybe even feel that chemistry zing that’s missing when you’re dealing with a photo and words on a screen.

I’d get four minutes per date, which I thought seemed pretty quick, but then again it’s called speed dating, not a reasonable amount of time dating.

The night of a thousand-speed dating dates

Okay, so it was only 20 dates, but that felt like a whole lot considering I’d only been on one date for the whole previous few months.

Right up until the event I’d been super jumpy and excited but when the night came, that turned to nerves. How would I seem cool in four minutes? How would I know if someone else was interested?

Most importantly: What should I wear? I’m both a fancy dress and jeans and heels kind of girl so I couldn’t choose which was more “me”.

Because I am indecisive, I put up a poll on Facebook giving the options of jeans and a nice top, and a dress. And because clearly, my entire friendship group is also indecisive, the results were almost entirely split down the middle. I went with jeans, heels, and a nice top to give a sort of casual but classy vibe. The last thing I wanted was to give off a high-maintenance vibe. I literally had four minutes so impressions matter.

I wondered later whether the jeans had had any effect on my night. Because hi, my name is Liz and I’m an over-thinker.

When I arrived, I was pleasantly surprised. Far from the room full of nerdy, desperate, and dateless people I’d feared, the trendy bar was full of cute, fun-looking singles. I even was immediately attracted to one of them!

I grabbed a drink and then it was time to date.

Out of the 20 men I dated, there were only two that were “Definite no!”s. One of which, when he found out I was a dating writer, interrupted me abruptly to say “Okay, so how does a guy in his early 20s find a girlfriend in under three months then?” I tried to kind of laugh it off and say, “Oh you know, these days the bar is so low that ...” He didn’t let me finish.

“What do you mean the bar is low? The bar?” he said, gesturing to the literal bar and puzzled bartender we were standing next to. “No, no,” I said, trying to add gestures so he understood my meaning. “I mean the bar is so low, like, you know the expression?” Mr. Abrupt continued to stare at me. “You mean the bar is low, like on alcohol?”

My inner English major cringed, and I just said: “You should be fine, buddy, just don’t be a jerk.” But no, he wouldn’t let that go. “Nah I don’t care about like how you act, I’m talking where do you go? Where do you meet chicks?”

My god, this was the longest four minutes of my life.

But the rest of the dates? The rest were awesome! The banter came so easily, and so many of the guys had excellent chats.

I felt like I was on fire, having conversation after conversation that just felt so good. I was getting compliments left, right, and center (“You have the most memorable face in the room”… my Gawd, I was practically fanning myself!) and many of the men seemed really upset when our four minutes were up. Several said variations of “We definitely have to continue this conversation,” and made motions to write my name down on their match cards.

Out of my 20 dates, I ticked yes on 9 people. Solid four definite yeses, and five guys with definite potential that I wanted to explore. I walked out of there feeling like my ego was at its highest in years and went home to sleep with a smile.

Oh you sweet, naive summer child Liz. Winter is coming.

The speed-dating fallout

I woke up to a message from my lovely male plus one I’d dragged along as my “vouched for” guy.

“How did you go with your matches?!”

“Oh yeah!” I thought, springing up in bed and checking my email. I’d had such great interactions with these guys, and at least five of them had indicated in person that they really wanted to see me again, so I was pretty confident.

My inbox refreshed: newsletter, newsletter, social media update, bill (ugh) ... That was it. No email from the speed dating company.

I asked my friend when he got his matches sent to him and he said late the night before. The night before?! I told him I had no email.

“Oh,” he said. “Well, maybe they’re just doing the people who didn’t get many matches first? I only got two, so maybe they’re taking longer to process yours?

It was a lovely thing to say, and I tried to believe it but ... I kind of didn’t. Also, my anxiety was sitting on my shoulder telling me that absolutely wasn’t the case, the little jerk.

I went to work that day feeling anxious, refreshing my email like a crazy person. By the middle of the day, when I still had no email I decided to contact the company.

“Hey guys,” I wrote. “Had such a fab time at the event the other night. So I hate being “that girl” but hello anxiety! I was just wondering… two of my friends who went to the Brisbane Speed dating event got their matches sent to them already but I didn’t get an email yet. My overactive brain was wondering if you just haven’t gotten around to sending them all through, or if it went technologically missing?”

I felt like such a desperate, pathetic idiot, but I just had to know.

About an hour later, my phone pinged with a reply. “Thanks so much for getting in touch! Something might have gone wrong because we definitely sent your email over. So sorry you didn’t get it! Can we send it to a different email for you?”

I let out a breath I didn’t realize I’d been holding. “Yes please,” I typed. “Thank goodness. I was beginning to get worried!”

Seconds later, I opened my inbox, and there it was. The email with my matches … Or should I say match. As in, singular. With one guy. Who I couldn’t actually remember meeting at all.

I ran through my mind all the guys I’d ticked yes on and this one didn’t ring a bell. At all. In fact, I wasn’t even sure I had ticked yes on anyone with the name staring out at me from the screen.

And suddenly, the massive high I’d had from the night before came crashing down. Out of nine men – nine! – I got one match, who I was pretty certain I’d not actually picked. Maybe the organizers felt sorry for me and had given me a pity pick.

My mind was working overtime with all the dates from last night.

Mr. You Have The Most Memorable Face In The Room ticked ‘no’? The guy I was instantly attracted to said ‘no’. Every single one of the guys who had told me, unprompted, that they 100 percent definitely wanted to see me again, had all ticked ‘no’? Even the guys I was “meh” on, but was not opposed to seeing again, ticked ‘no’?!

And all of a sudden, all the feelings washed over me and I started to tear up. Granted, I was PMSing really bad, but I just couldn’t help but wonder what was wrong with me that not even one out of the nine I picked me back. Was it the jeans? Was I too forward? Were the men intimidated by my confidence? Suddenly all my self-esteem fears that never entered my mind while online dating was flooding me and I felt like I was drowning in self-doubt.

See, with dating apps I expect it to be a terrible cesspit of human grossness and it’s a pleasant surprise when it isn’t. Which is rare. With online dating I know my value, I know what I will and won’t accept from people, and when people are jerks I feel like that’s on them, not me.