Women love compliments. FACT. Women hate compliments. Bizarrely, also FACT. The incompatibility of these two statements has vexed me since I first uttered the phrase “that’s a smashing blouse you have on” and was met with “why is this stalker talking to me?”

I’m generally someone who likes to say nice things to people. I soon learned that saying nice things to male friends was misconstrued as “a bit gay” and so I now limit my conversations with men to things like “Oi dickhead”, or something even nicer like “You’re a prick but not as much of a prick as him” and if I really want to be complimentary to a male friend I will push the boat out with “I’d shag your sister” – truly the highest tribute that can be paid from one man to another.

Sadly, complimenting ladies is not so simple – it’s a total minefield, but a minefield where the mines never kill – they only maim, and you have to live with the consequences for the rest of your life. (I should point out that is just a metaphor, I have never actually been wheelchair-bound as a result of a mistimed or misjudged compliment, although I have been threatened with it many times).

I’ve been thinking about this topic a lot recently, as I was doing some serious research into the viability of the “honest compliment”. Compliments are often so wildly exaggerated that they can lack credibility; I wondered if there was way to give a realistic compliment which would be more believable and yet also flattering as intended.

An opportunity to try this out came along recently. I was standing having a cigarette in my usual place. A pretty young thing came out of the wi-fi hotspot across the road (I think it also serves coffee or something, but I’ve never seen someone go in there without a laptop, iPad and a shivering hunger for network connectivity). She approached me. I was sure she was primed to say “hey, I couldn’t help but notice you while I was checking Facebook in there. I’ve actually got a real fetish for guys who are simultaneously fat AND skinny. I’ve got some nudey photos on my phone I can Bluetooth to you, AND I explicitly authorise you to show them to your friends in the bar tonight.” Either that or she wanted a cigarette off me.

Much to my surprise and excitement, she did not want a cigarette, so it was obvious that my original fantasy was going to come true. I mean, what else could she want.

“Do you have a lighter?” Fuck’s sake. OK, well at least it was a conversation with a woman. I reached into my back pocket. It wasn’t there. I cursed myself for putting it in my front pocket yet again. I reached in the front pocket, it wasn’t there. I stood confused for a few seconds, and then felt something trickling down my leg.

My immediate thought was I’d wet myself. But surely not; I’d had an actual girlfriend mere months ago, usually it’s a drought of years before the sight of a pretty girl would get such a panicked reaction. There was a rattling by my foot, and I looked down, there was my lighter. The reason I have to keep reminding myself not to put my lighter in my front pocket, is that my front pocket of those jeans has a hole in it.

She took it and then started rummaging around in her bag looking for her smokes. There was an awkward silence. I had wondered in the past if this was maybe a good kind of opportunity to talk to girls. I mean, she’s indebted to me for the lighter, so if I start chatting to her she’s far less likely to call the police. And if she screams and runs away I can justifiably chase after her to get my lighter back. Maybe this was the ideal time to try out one of my new realistic compliments.

At first I thought to say to her, “You know, you’re definitely the cutest girl I’ve seen while I’ve been smoking this cigarette.” Blistering realism. It was definitely true. But I doubted whether she’d be flattered, my cigarette was only half done. OK, how about “You know, you’re probably the cutest girl I’ve seen all day.” A very genuine statement (as long as the “probably” was included, I didn’t have time to run through in my head all the girls from the Tube). Problem was it was only 11am…

She continued to fumble around and I started to think I would finish my cigarette before she’d found hers, and have to ask her to post the lighter back to me.

It gave me thinking time though. How about “You know, you’ve got quite an average face, but you’re probably in the top 10% in terms of legs.” Again, I couldn’t be sure this would come across as flattering as it sounded to me. “You know, I’ve seen 10, maximum 20 girls in the past 3 days that were more attractive than you.”

She finally found her cigarettes and lit one up. I didn’t have confidence that any of my realistic compliments would be taken well. I abandoned the idea and put my hand out to take my lighter back.

“Hang on, one second,” she said. She put her bag down and lifted up one side of her short and tightly-fitting dress.

I didn’t even have time to say “You know, you’ve got the second best thighs I’ve…” before she put my lighter to the bottom of her dress. As the flame appeared, I realised this was definitely the first time a girl had ever set fire to herself after talking to me.

OK, you are the hottest girl ever, can I have my lighter back now.

OK, you are the hottest girl ever, can I have my lighter back now.

She let go of the lighter after a second or so, handed it back, and with a thank you made off. I can only imagine she had a thread or something dangling off the bottom off the dress that she wanted to get rid of. I was too busy looking at her silver trophy winning thighs to really notice.

It was back to the drawing board, but my experience had led me to formulate my first definitive rule about complimenting women.

1) Realistic compliments are not flattering

“Out of the 3 billion women in the world, you are definitely in the top million.” Now that sounds like a fantastic compliment. If I was told I was in the top 0.03% of the male population, I would be fucking ecstatic. It is not the way with women. You tell a girl there are over 900,000 hotter girls out there, you’re asking for trouble.

And I soon discovered that there are even more rules about these things, passed down to women from an early age. You remember at school when the girls all went off to a special class and refused to talk about what it was. This had nothing to do with periods; they were being coached in the ‘rules’.

2) The value of your compliment is directly related to how attractive you are to the girl

If the girl think you’re hot, your compliment will generally go down well. She’s hearing what she wants to hear from a person she wants to hear it from. If she doesn’t think you’re hot, you will come across like a recently-released sex pest. When the non-hot guy says “You’re really pretty” he might as well be saying “I usually only masturbate over you in the evenings but I’m sorely tempted to just start doing it right here.”

3) Your compliment is taken in the context of your perceived taste in women

Put simply, if you’ve previously heaped high praise on slutty looking girls with their business hanging out, or spoken highly of girls going for the high-class escort look, then when you tell the pretty English Rose type “you look amazing today” she’s immediately going to think she’s accidentally walked out of the house wearing only half her outfit.

But it’s actually more complicated than this. I am known to like curvier girls, and I don’t discriminate against a girl who has some substantial holdings in the arse department. So, when I compliment a girl’s figure the mental process goes like this: he likes girls who have an arse = he likes really fat girls + he likes me = I must look really fat, and the response is “Oh. Thanks Alan. That’s sweet. No no, I was finished my salad anyway, I’m full, and expect I won’t need to eat ever again.”

4) You can’t compliment multiple women

“You’re really hot, and so is your friend, and so is your sister.” This is a no no. It gives the impression that having the required number of limbs means automatic enrolment into your roster of honeys. This can be frustrating as often hot girls hang around together and hotness can run in the family. Nevertheless this should be avoided.

Even being heard to compliment other girls sporadically can be a negative. Over a five year period you might publically describe many girls as hot. Your compliment will then be met with “yeah but you like everyone.” Women don’t seem to understand that there actually are a lot of attractive girls out there, and being one of them is a good thing.

No, she has to be only one. She must be the most beautiful girl you’ve ever seen and the only girl you’ve ever been attracted to.

5) Never tell someone she is the most beautiful girl you have ever seen and the only girl you’ve ever been attracted to

She will think you are a stalker. You see how complicated this business is.

6) Words must be chosen carefully

“Hey, cute shoes” is OK. “Oh my God, you are fucking breathtaking, how did you even get that face the way it is?” is not OK.

Wording can also be misconstrued once they have passed through the neurosis filter in women’s brains. I went through a phase of really liking girls with chubby cheeks (known as my Judd period), and this is absolutely not a phrase you want to use to compliment a lady. I discovered at university that “Hey I love your chubby cheeks” is generally answered with “Are you saying I’ve got a fat face”. You might as well say “Hey moon-face, are you made of cheese?”

Nine times out of ten a well-meaning compliment will be twisted into an accusation of obesity, so guys have to be very careful. Note that women can perceive any of the following words as meaning “fat”: “curvy”, “shapely”, “well-rounded”, “feminine”, “demure”, “natural”. And in some extreme cases also the following words: “nice”, “pretty”, “hot”, “beautiful”, “cute”. And sometimes even these words: “slim”, “skinny”, “petite”. That last group is translated as “fat” when the woman’s built-in neurosis filter combines with a defective sarcasm receptor.

7) Some areas are off-limits

I was dating a girl last year and I wrote a song about her vagina. Words and music. You could say it was a flower ballad. It did not go down well, which was a little ironic.

8) Comparing girls positively to their friends is off-limits

OK, so she has a really hot friend, and you might think it’s a great idea to say “Hey, you’re so much hotter than your friend!”

“How can you say that?! She is super-hot, I mean look how hot she is, let me show you 47 other pictures of her looking hot, she so hot, everyone thinks she’s the hottest and I’m totally OK with it, I mean look at her waist, and she’s got the most amazing boobs, she’s so hot, I WISH I was that hot.”

Likewise, don’t ever say “Yeah, your friend is hotter than you.”

“Oh. OK then, I’ll just crawl back under my fucking bridge then. Anyway, she’s got cellulite, you do not want to see her in a bikini. Let me show you a pic of her in a bikini. See! And look how drunk she is in this one, she’d just thrown up. But, fair enough, if that’s what guys are into.”

The only way to address this is to maintain that any girl is exactly as attractive as every one of her female friends and siblings.

Finally the golden rule:

9) Never, ever, no matter how much they beg … never ever compliment a girl’s personality

You are basically saying they are ugly. And fat.

If you mess up with any of these rules, whatever you do, don’t try to wriggle free of the situation. Just feign illness, or set off a fire alarm, and leave the area. I will leave you with the tale of how much worse you can make things if you stick around and try to dig your way out.

I was on my third date with Alice, who you may remember from this story and this one; we were in a pub together killing time before going to the cinema. I had been heaping compliments on Alice’s visage and was trying to convince her that she was very photogenic, something she had refuted since the earliest times I’d known her. I took out my phone and asked if I could take a picture of her. She flat-out refused.

I tried to persuade her, but it wasn’t just her aversion to photos that was the problem.

She said “I don’t want you looking at my photo later on and having all kinds of ‘dirty thoughts’…”

Ouch. OK… Without really thinking it through I knew exactly what to say to put her at ease. “Oh, no no no, don’t worry about that. I promise I wouldn’t have any such thoughts looking at your photo.” Surely this was what she wanted to hear. “In fact, whenever I’m having such thoughts I would never think about one person anyway. It would be a mixture of people. Like the face would be maybe some horsey girl that I like, with maybe a bigger nose, because I like Jewish girls, and the arse would be from someone off television, and the boobs would be the girl from the Tube who looks like Kelly Brook, and then there would be various other bits from people from films and some girls I used to work with, and a couple of my friends’ friends, and they would all be merged together into one really weird looking girl who has all the bits I like rolled into one.”

And then I said the word that I came to regret most, the word which summed up this creature I would think of INSTEAD OF THE GIRL I WAS SEEING, AS PER HER REQUEST, “Basically like some kind of ‘Frankenhorse'”.

“Did you just say ‘Frankenhorse’?”

“Um, yeah well she’d be quite horsey and with all bits from all the other women… I mean I’d just be cherrypicking all the best bits from various women.”

Alice didn’t look too flattered by this cast-iron reassurance that I would not be fantasising over the photo. “And what parts of me would you cherrypick, dare I ask? If any…”

“Um, well it’s entirely up to you, I can maybe swap out the boobs and you can supply those, any part you like really? Hang on, mere moments ago I was being accused of using a potential photo of you for nefarious solitary purposes, and now you want IN on my Frankenhorse?”

The mood became frosty, inexplicably, all of a sudden. Thankfully, it was nearly time to head off to see the film.

I never got my photo, but I learned an important lesson – that sometimes it’s better to just shut the fuck up.

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