Hurting a woman’s feelings is putting me off trying to find love.

I recently watched the film Inside Out 2.

I saw the original when it first came out in 2015.

In the sequel, 13-year-old protagonist Riley repeatedly says four words that struck a chord with me. Largely because, in the 72 hours prior to seeing the film, I’d been telling myself the exact same thing.

“I’m a bad person.”

Three days prior to viewing Inside Out 2, I went on a blind catch-up (not date) to a nearby playground. I don't like to sit during catch-ups/dates. I prefer to do something active the first time I meet someone, like fly a kite, play ‘around the world’ on a netball court, or even just go for a walk.

On this catch-up, we chatted as we walked around the playground.

I walked over to the wooden train, stepped up into the cab and pretended to be the driver, “Final call to any passengers travelling to Paris.”

“Oh yes of course,” she played along, “I’d love to catch a train from Melbourne to Paris across the ocean.”

“Have you got a ticket?”

She picked up some nearby bark and dropped it in my hand, “Will this do?”

“Oh, first class. Come this way m’lady.”

She smiled at me, and I smiled back. She sat, and I turned away and took the wheel, and began the (fake) adventure.

“Ladies and gentlemen, if you look out your window, you’ll see the Indian Ocean. That may only seem like a small puddle caused by last night’s rain, but it is in fact 70 million kilometres of sea water.”

I didn’t think she’d keep going along with it, but she did. “Oh my God,” she said melodramatically, “there’s a dog standing in the middle of the Indian Ocean.”

There was a golden retriever standing in the puddle.

Driving the train, I was sprightly, making up cheeky stories, and asking her questions about her hobbies in life. But on the inside I felt terrible.

Why? Because after only five minutes of knowing this woman, I’d made up my mind that I only wanted to be friends with her. And I hated myself for it.

I was in ‘Riley from Inside Out 2’ mode, and was repeatedly chastising myself for being a bad person.

‘Good on you guy, go ahead and make someone else feel rejected. You know how that feels and it sucks.

‘Wow, you’re not just a bad person but a conceited one as well. Who says she even likes you anyway?!

‘A good person would give it a chance regardless. Clearly that’s not you.’

I was courteous and invested for the next half an hour, and while I thought it was more respectful to do that than be cold and removed, the self-hate continued.

‘That’s it, moron, mislead her, which will make your rejection all the more hurtful.’

In the end, there was some level of disappointment in her expression when I told her I wasn’t feeling the chemistry, but she was polite and respected my honesty.

Not that it subdued the thoughts in my head.

‘The next time a catch-up happens, the reverse will rightfully occur, because that’s what you deserve.’

I broke everything down with a female friend a week later. A female friend who was able to empathise with me regarding my inner critic.

“I have a couple of poisonous neurons running through my brain as well,” she said. “And I actually had to let a guy down last month, and I felt a similar way. But it doesn’t mean I’m a bad person, it just means I don’t like hurting people’s feelings.

“Some will say you’re making a big mistake by not giving it a chance, but every person is different, and every situation is different, and if you know and trust your heart and how you feel, then you should follow that every single time.

“Don’t let hurting a woman’s feelings ever put you off trying to find love. No matter how many times you reject a woman, or a woman rejects you, as long as you express it or receive it with integrity like you have been, then in that context, you’ll never be a bad person.

“And let’s face it, if you pursue something when your heart’s not in it, you’re doing the woman a disservice – you’re getting in the way of the next guy who comes along, who may actually be her one and only.”

I was amazed at how this female friend of mine was able to identify all of that and then articulate it, and in doing so, take me from a place of abandonment, to a place of hope and reassurance – that I’m actually not that bad-a-person.

It was a reminder of how fortunate I am to have a female’s perspective, from a woman who allows me to be vulnerable and not judge me for it.

But the dust has now settled, and I’ve returned somewhat to again scrutinising my behaviour at the playground, particularly the way in which I let the woman down.

And I’m left asking myself two questions: Is what my female friend said right? Or is there a kinder way to go about it for the sake of the woman I’ve just met, and so that I’m not stricken with thoughts of being the worst guy ever?

So... is she? Or is there?