I’m well-known for my way with words with women, sadly not quite in the manner I’d hope for. If there’s something inappropriate to be said I have a habit of saying it and if there’s a back-handed compliment to be made I’m usually the first to make it. I never mean anything wrong, I’m very well-intentioned, but I have a habit of trying so hard to say the right thing I end up saying exactly the worst thing.

I think it stems from my basic inability to pass a good gag by, and that my internal monologue is constantly doing stand-up, pumping out gags in situations where I really should be handling the situation calmly and seriously. All I end up doing is getting myself into trouble.

For example, when introduced to a very attractive girl with enormous breasts, I was very conscious of being distracted by the obvious. So I greeted her with “Wow, you’ve got a really nice face as well.”

I used to work with a girl who I knew only as “horsey”. She had an incredibly horsey face, and for me that’s a good thing. It was a compliment, a term of endearment. I was once in the lunch queue a few people behind her and said to my colleague “hey look there’s horsey.” She turned around. I just started whistling. She had a pony tail too which I found particularly appropriate. And then there’s the nicknames I’ve given to good female friends which somehow have stuck. Gypsy… Poochy… even Big Tits. There’s nothing like answering the phone in a busy office with “Hey Big Tits, how are you?”

Of course around certain topics, like girls’ weight I am much more tactful. I was chatting with a friend and she was talking about how she wanted to lose a bit of weight, especially around the bum/thighs area. I kept telling her not to worry about it and she looked great (seriously she’s hot), but she really insisted she wanted to get a bit slimmer down there. I said to her “look, loads of guys I know have said to me they think you’ve got a great arse.”

She seemed flattered until I said, “And not all of them were black.”

Women love me really, look I'm surrounded by them.
Women love me really, look I’m surrounded by them.

On that topic, I was told off quite severely once for calling a girl “brown”. She said that was offensive and said I should call her black. I swear to God, and I know I’m not colour-blind but this girl’s skin is brown. It’s definitely brown. But I took the criticism on board and decided if that’s how she wanted things to be described that was fine with me. I’m adaptable like that, constantly tailoring my personal communications to suit the situation. It’s a great life skill. So I saw her a few days later wearing a tan-coloured top.

I said “That’s a really nice black top you have on.” See I’d learned. “In fact, that black top really matches your black eyes.”

When I was in hospital briefly last year the doctor’s kept asking me if my stool (medical term for faeces (technical term for poo (inoffensive word for shit))) was black. I wondered what would happen if this girl went to the hospital with stomach pain or vomiting and they asked her if her stool was black, and she said “Always.”

I’m teasing of course, I know what she meant.

My ex-girlfriend was German (she still is), and me and her very rarely argued but one night she was moaning about something or other, and really getting in my face. I said to her “Stop invading my space. I’m not Poland.”

Sometimes I just don’t know how my remark has been taken. Back when I was smoking, a girl once walked past me while I was standing having a cigarette. She was really cute. Cutest girl I’d seen in ages. She had this thing wrong with her leg, something more serious than a limp, that was making her walk very funny, but I was just gawping at how cute she was. As she walked past me she growled at me “what are you staring at, haven’t you ever seen a disabled person before?”

I said without thinking “I was staring because you’re fucking hot, I barely noticed you were disabled.” That was a nice thing to say right?! She just shrugged and hobbled off. I just can’t win.

I don’t even need to be face to face with the person. You’d think with the consideration that goes into writing an e-mail I’d be spared these kind of outbursts, but no. I had been contacted by a girl from an online dating site, one of the things she did for her job was write newspaper headlines – I thought this sounded like a dream job. I asked her if she wrote puns, she said sometimes but that a lot of the stories she covered were for serious things like stabbings.

I replied with “Grammar school teacher punctuated by six-inch blade.”

Never heard from her again… I think what I’m doing wrong on the dating site, and in real-life, is I’m just being myself, and fundamentally I am completely undateable and the kind of person who can’t be around women without making some kind of (fairly witty but) completely inappropriate and off-putting remark. And yet I am so well-meaning and innocent. In fact, up until the age of about 24 I thought oral sex was just talking dirty…

One of my best recent gags was actually just after a girl had left the room, but it just wouldn’t have worked if she hadn’t…

I was at the opticians for about the tenth time in as many weeks, trying to get contact lenses out of them. They had messed up appointments, lost my trial lenses not once but twice, got me the wrong prescription and generally cocked up at every possible opportunity. I was trying to keep my sense of humour as I arrived for a contact lens post-consultation check-up pre-assessment. The assistant showed me in to see the optician and I sat down, having memorised what I was going to say when he asked me to read out the letters on the wall. “Um, G…. I, V… E, M, E, M… Y… F,U…. C… K, I, N… G … L, E… N, S, E… um, S.”

He spoke with the assistant, “Ah Lorraine can you just get me a bottle of the peroxide solution for Mr McCann’s new lenses?” and she walked off.

I said “I might not be needing them anymore…”

He said “Why?”

“I can see clearly now Lorraine has gone.”

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Don't just sit there, say something, the silence is freaking me out!