Just good friends: Pat McKenzie and Sam Hand on Valentine's Day (Photo: Amy Seaborn)

Valentine’s Day: so how did that date go?

We all wish we could get the perfect Hollywood version of a date – particularly on Valentine’s Day. But in most cases, they are weird or uncomfortable.

There are the lucky few who walk away with a romantic, cute or meaningful story to share – meanwhile, the rest of us can only laugh at what seriously went wrong.

Here are a few cautionary tales of dates that didn’t go to plan – and a couple of less squirmy ones.

Mr Rich Guy

I went on a date with a guy from Tinder, so in retrospect I brought this on myself.

We went out for Mexican in Circular Quay at this place which was swanky and inauthentic, but bougie enough that you don’t mind. He spent the entire night talking about his parents and their money, going on to out his mother as a trophy wife.

When the bill came, he insisted that “the breadwinner” pay – courtesy of mum and dad, presumably.

When we took a stroll around the Quay, post-soft tacos, he pointed across the water to an apartment and said: “That’s my place on the second floor.” I bailed with a faux shift the next day. Total yikes.

– Holly, 19

Keep it in your pants

I went on this long drive with a guy I met on Tinder and had made it clear that we were looking for something casual.

We drove around for a bit, talking about ourselves. Then he was like, “Let’s stop for a bit,” and I was like, “Okay.” We stopped at this playground/park, sitting down listening to music.

We started making out and he was gesturing for me to go down on him, but I said “no”.

He requested a few more times, and after the fourth time he said: “It’s getting late, let’s take you back to the station.”


After that, I blocked him on everything.

– Ankita, 23

Blind date

I went on a blind date set up by a friend when I was 19. I wasn’t super keen on the idea but it was all organised, so I thought: “What the hell? I’ll give it a go.”

So the day comes, I go to get the train because there’s no way I’m facing this one without Pinot Gris on my side, and the train is cancelled. So is the next one. I turn up an hour late.

The guy is pretty nice about it, considering, and we have a few drinks and get chatting. It all seems to be going well, and I offer to get dinner as he has paid so far, and I’m nothing if not a strong, independent woman. Without a wallet, as it turns out.

I had left it (my wallet) at home. so the poor guy had to foot the entire bill.

Then I suggest a game of pool to break the tension. He agrees but warns me he plays competitively. I reassure him I’m a shocking player. Well, the gods blessed me with something that night and I turned into a complete pool shark and won three games in a row.

Actually, on reflection, it was a great date for me. I just feel bad for the guy.

– Penny, 24

Not my baby

Long Jetty, Central Coast: the perfect location for a date (Photo: Amy Seaborn)

I reconnected with a friend who I hadn’t seen in ages and after a long chat, late into the night, we both realised at one point or another we’d both had feelings for each other.

We decided maybe we should try going on a date. We set a time and we started getting a little flirty. The big day came and I go over to her place. We wanted to keep it fairly casual, so we decided on a lunch date and maybe hanging out after.

We went to lunch in Long Jetty, to a café I love, and she was taking ages with the menu, sending the wait staff away multiple times.

Finally, she asked if she could have the burger without cheese, telling the waitress really casually that she was pregnant and couldn’t eat cheese.

The waitress turned to me, then her, then me again, then back to her, smiling, and said “Congratulations!” I fell over my words, trying to say “Not mine” and “What?” to my date. We finally got it together and the date got back on track, but not by much.

After going shopping, we went back to her place. I gave her a massage, and then she asked me to make dinner. When it was ready, she served the entire thing into one bowl (for herself), then went back to the movie.

I decided to call it a night. As I waited for my Uber, she texted me: “I think I see us as friends.” No shit.

– Josh, 26

Opposites attract?

I went out with a girl (before my gender transition from male to female) from my fitness class.

She thought I’d be this big tough jock, probably due to me being a fitness instructor with muscles, and I thought she’d be demure and really feminine due to her looks.

But it turned out she was really good at fixing cars and worked for a car yard.

She was a huge tomboy and I was a bit of a girl, so our preconceived ideas of each other were totally wrong.

I remember how awkward and disappointed I felt after that date, and I know she felt the same, as it was awkward when I saw her at the gym after that.

– Caroline, 53

The first date

Deciding what to wear for that first date (Photo: Amy Seaborn)

I started talking to a guy on Tinder and we made plans to meet up for a first date. We agreed on going to a movie. When I asked what time the movie was, he told me … (we were going to) a movie theatre 40 minutes away.

I started freaking out because I was already so nervous, and now I had to worry about a long car ride. I was pretty quiet throughout the car trip, but he made me more comfortable by singing along to his music, which was pretty cute.

We finally made it to the theatre, only a few minutes late, he bought our tickets and, as we made our way in, he held my hand – we held hands for the majority of the movie.

Afterwards, we got dinner. I was still so nervous, so I couldn’t eat the small salad I had ordered.

I felt so bad because he had paid for it, but he got his money’s worth by finishing it off.

We ended the night by going to a look-out point overlooking the ocean – how romantic – and shared a few kisses.

We might not have worked out in the end, but it was a pretty good first date.

– Amy, 20­

Just not cricket

My boyfriend said he was taking me out for the day and that it was a surprise.

I thought: “Fab! Lunch at a nice restaurant, harbour cruise…” My imagination went wild.

We jumped in a taxi to Sydney and we ended up at the cricket ground. My surprise for the day was watching the cricket.


He was chuffed and I was not.

– Louise, 47

– @seabornamy