Scottie is asked for feedback on a date. Honestly. And now he’s going to Hell.

As this column is proof, there’s no denying that I’ve had my fair share of disastrous dates. Still, I can’t seem to run a mile when I notice that it’s not going to go well. My friend Paul recently told me to just give a pre-prepared excuse and make a dash for the nearest exit; something like “oh I really must go, I just remembered that I left my mother in the oven”. Or maybe “oh, I’m so sorry, but I have to say goodbye to my cat before she’s launched into space”. And then run. RUN.

Instead, I endured another addition to the series, yet even when I was free and walking home, he texted to see what I thought of him. I sent a reply that wouldn’t be too harsh; that I had a lovely time, but I didn’t feel any chemistry. Then I got a message that was something new:

“Just let me know what I did wrong, so I can improve for next time.”

My heart sank, but part of me wondered if he was also going to ask for a written reference to go with it. Usually, if I politely say to a guy that our first date will also be our last, I’ll get some sort of acknowledgement that the message has been received and we leave it at that. This guy was different, yet I should’ve known that things weren’t going to be as easy.

This is where I should probably go to Hell, but I gave him what he asked for. I told him where he went wrong. I mentioned how admitting to me that he was “really boring” was hardly going to attract me, that he’d usually be expected to ask the odd question in a conversation (because I quickly got fed up being the only one to ask), and that randomly saying “hey, let’s get married!” might just scare the living daylights out of me.

Believe it or not, I’m not so heartless as to give these tidbits of advice in a callous way. I had to sit down and put the brain gears in motion to give him the critique he wanted, without hurting him. On the other side, I had to make sure that he knew I didn’t want to give him that second chance; sixty minutes of forced conversation in his company was more than enough.

The date itself was doomed from the start. He was a bit of a rocker type, although most rockers have life, passion and aggression in them. Instead, this rocker found the emotional version of Botox; he seemed to have no interests, no passions and no life. He travelled a bit – a topic which I held onto for dear life – but “nowhere too special”. One thing he genuinely seemed to like was tattoos, which gave us a good six minutes and twenty-two seconds of decent conversation. Still, when I asked why he liked them, he gave no proper reason; “why not?” was his reply. Fascinating, and so deep.

They say the topic men like to talk about most is themselves, but that isn’t entirely true. While my date gave his best impression of a painted wall slowly drying, my mind started to panic over what was left for me to talk about. Eventually I couldn’t handle it anymore, and made my excuses to leave. It wasn’t long afterwards that I got his request for a critique, but he didn’t seem best pleased when I tried to let him down gently.

“Please don’t jump to conclusions,” he replied. “I thought we were getting to know each other before jumping into anything. I even wanted to hold your hand, but thought that might be a bit forward.”

His response made me wonder if I was dealing with someone who was either a bit touched in the head, or genuinely didn’t have a clue how to date. Either way, the latter applied, but I was slightly concerned for him now. Still, I remembered a brief line he said when we were chatting online before the date:

“I don’t go on too many dates… usually they don’t want to see me again after the first date.”

Ignoring the neon-lit warning signs, I passed his remark off as a humble gesture at best, or at worst, an admission of a recent unlucky streak – something we all go through from time to time. Now, though, I realised that it was probably very true, and I was the latest addition to his bad luck. But how do you sensitively tell someone that they were like a human form of valium? Ignoring his request for a second chance (your instincts are at their most accurate within the first few seconds, I reckon), I offered the ‘let’s be friends’ card, which he wasn’t too impressed with:

“No point. We’ll meet up about three or four times as mates to be polite, then you’ll lose interest and I won’t hear from you again.”

Impressed with his eternal optimism, I gave in and let him achieve his self-fulfilling prophesy by replying with a simple “fair enough”. Normally, I’d genuinely intend to be friends with guys if there’s no romantic spark to be felt, but the negativity from this guy was becoming stifling.

In some ways, we both learned something new from that date. He learned that asking questions can go both ways, and that a guy needs to be interested in something before he becomes interesting. On the other hand, I learned that if someone asks for help, what they’re asking for might not help them at all.

[To read the previous instalment of Scott’s column, click here.]

‘Scottie’ Illustrations by Stephen Charlick