2 Women on the Worst Dates They’ve Ever Had, and an Expert on How to Deal With It

How I Met Your Mother

There’s no doubt first dates can be incredibly emotionally draining. They require you not only to be on your best behaviour, but also to be considering whether the person you’re meeting is or isn’t a good potential match. It’s no wonder you can leave a first date feeling completely mentally exhausted.

If that’s what you’ve been experiencing time and time again, recently, or even if it’s not and you’re in a happy, committed relationship and are just curious about how the dating scene is these days, these bad dates from two Sydney women should offer you some (juicy) insight.

Kaity, 34

I met this guy on a dating app a couple of years back. He told me he was a lawyer — not that his job matters but he would go on and on about it, talking about cases he had that were stressful etc. We decided to meet up at the Opera Bar for drinks. I never really go to Sydney Opera Bar because I am so afraid of birds — always have been.

Anyways, we get there and he was already super drunk by the time he arrived. He then tells me he is actually a PE teacher and that he had been recycling stories from his mate to girls because we are all shallow and wouldn’t date a PE teacher.

He then proceeds to throw his hot chips at me so all the seagulls would swarm me. It was traumatic! I picked up the bottle of red (that he made me buy) and went and made friends with a group of girls at another table and drank with them.

On another crazy date, I met up with a guy I met on a dating app, and he would always keep one hand in his pocket. I asked him why he would do this, so he took his hand out and he had no fingers. He told me a shark had eaten them and then said “It’s okay, though, because they will grow back.” He legit thought fingers grew back.

Lyndsey, 40

When I was living in NYC, I once matched with a lawyer on a dating app. We met for a drink at a cool cocktail bar in Chelsea.

I felt like he was really trying to sell himself to me, which I could forgive I guess as NYC dating is competitive and fickle and people feel the need to tell you as much about themselves quickly, so no one wastes any time. But this guy was just really going hard, and it felt like he was in a job interview telling me why he should get the gig.

Finally, he asked some questions about me, and I started telling him about my life/career/hobbies etc, but it seemed like he wasn’t really listening but just waiting for a chance to jump back in with info about himself.

Then, a girl came up to us and said, “Sorry to interrupt, but are you XXX (I’ll begrudgingly keep his name secret to respect his privacy) from The Bachelorette?”, which, as it turned out, he was. After the girl (who I strongly suspect he arranged to be there) walked away he turned to me with this smirk on his face and said, “Yeah, so I have some TV experience too.”

First off, if you know me, you know I LOATHE reality TV so this was not happy news for me. Second, I was mortally offended that he considered going on a terrible dating show (and losing) even remotely close to the years I had spent hustling and honing my craft [I’m a TV presenter].

I mean, I’ve won plenty of arguments in my time, but I don’t go around telling people I have experience as a litigator. Anyway, this all happened during a time when I was trying to be less quick to dismiss people and give them more of a chance, so I agreed to go out with him for dinner. Knowing that I have gluten sensitivity, he very kindly found a restaurant, not too far from my place that had an extensive gluten-free pasta menu. The second date was no better and he just kept on and on about himself so after we finished our meal, I said I was going to head home as I had an early shoot the next day.

He slammed his whiskey glass down on the table and was like, “I thought we could go for a drink.” I politely declined and he became like a petulant child. He then tried to insist on walking me home, to which I said there was no need because I was going in the opposite direction to him, and it would take me all of ten minutes to get home.

He tried the old “I’d feel more comfortable knowing you were home safe” I was like, “We’re on the Upper East Side and there are people everywhere, I think I’ll be fine.” So, he got all in a huff and said “FINE!” and turned and stormed off down the street! I was dying laughing all the way home and then he sent a text saying, “I assume you made it home safely.”

The next night I was out with one of my mates and relayed this whole thing to him so he decided to look up his social accounts for fun. At about 3am after our date, he had Tweeted: “I sprinkle gluten on myself to keep annoying girls away #gluten #annoying girls” in a reference to my allergy! We were howling with laughter — especially as I didn’t even have a Twitter account at the time so how would I have seen it, if not for my friend?

A few days later, he messaged me saying “I feel like our last date ended on a weird note but I wasn’t sure what you thought – would you like to go out again” I politely declined and he wanted to know why so I just said, “I don’t think we’re a good fit and I do better when I have conversations that are a little more reciprocal.” He replied, “I’m not going to argue with you….” and then proceeded to tell me all the reasons I was wrong!

There was about a metre of green text on my phone as he went on and on and on… finally, I just blocked him. He contacted me on IG a few years later when he saw we had some mutual mates saying “you might not remember me, but we went on a date a few years ago so I thought I’d say hi.”

I left him on read.

How to Handle a Bad Date

According to Kimberley Lee, a counsellor and therapist who specialises in dating and being single, there is in fact no such thing as a ‘bad date’. Lee says that all about reframing the situation.

“You can still enjoy time together learning about a new person while doing something you enjoy knowing it will be contained to that date and that you never have to see them again,” she says.

“Every date is valuable if you can also make space to practice gentle self-reflection: what did you learn about yourself? How can you use the experience to refine your dating approach or mindset? Or can you simply appreciate yourself for leaning into the adventures of dating and let the ‘bad dates’ fade into your dating history?”

As for the practicality of how to handle a date with someone you may not see yourself with long-term, Lee says to approach it with “radical honesty with a gentle kindness”.

“Trust me, you’ll feel a whole lot better about yourself if you handle the situation with sophistication,” she says. “Whatever you choose, and whatever happens, keep perspective and practice being gentle and kind with yourself.”

Ahead, Lee breaks down some simple tips:

  • Tell them as soon as you can gather the courage to have the hard conversation. The sooner the better.
  • Thank them for their time and let them know you’re not interested in pursuing anything further.
  • If they ask why, be honest but kind, and keep it with you so it’s not about them – because it’s not about them and it is about your decision. I usually say something like, “I’m not feeling the chemistry I’m looking for”, which is almost always the reason why I would want to end a date early or not see the person again.
  • Avoid trying to ‘soften the blow’ by saying things you don’t mean, such as “maybe we can be friends” (vomit – you don’t need more friends!), or “yes, see you again soon” (because you don’t want to and you won’t, and that’s a lie), or “I had a great time” when you didn’t because you both know you didn’t.
  • Stay with your truth as much as possible and know you don’t need to concoct some story about having to be somewhere urgently for an emergency. Rather, stay classy and adult — thank them for their time and excuse yourself from the situation without fuss or lies.
  • Remember it’s dating — it’s the process of auditioning potential people you want to share time and space with so take your time and stay connected with yourself and what you want. There are no obligations during the dating process and remember you’re allowed to change your mind. Part of this process is also having some uncomfortable conversations and if you can’t have them now, don’t wait until you’re years into the relationship hating yourself for not speaking up earlier.

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