IT is a dilemma that has at some point crossed the mind of every single man.

Is it okay to hit on my attractive female friends?

The answer of course is yes – although it can be complicated.

Usually the reason you haven’t already hit on them was because one of you was in a relationship when you met. This can be a major stumbling block.

If you met your foxy acquaintance through an ex, some misplaced sense of loyalty may put her off or, alternatively, if you knew her boyfriend you may feel a slight pang of guilt, unless of course she’s very good looking.

I have been romantically entangled with several of my attractive female friends – and many of the funny-looking ones, too – and this has caused a variety of relationship-crushing issues.

I was forced to look at this subject again this week when I went away for the weekend with a girl who combines the characteristics of being a dear and fascinating friend and being one of the most devastatingly attractive women I have ever seen – certainly in real life.

I met her at around 7pm on Friday with a window of almost 50 hours to work my magic.

After stealing a cheek kiss we sat down to dinner and fell into a lively conversation. But as we reminisced about old times my first glaring error became clear – I had told her far, far too much.

I laughed nervously as she repeated hilarious stories about my failed romances and public disgraces.

She would also be aware of my favourite pulling techniques and therefore on her guard if I suggested she drastically up her alcohol intake.

As the weekend progressed, I also realised the trust which had enabled me to share her room and talk to her about all kinds of saucy mischief was a double-edged sword as, to my horror, she seemed to be misinterpreting my flirtatious comments and light touches on the arm as platonic affection.

It was clear any advance short of hot lip action would be passed off as a playful joke.

However, after weighing it up I decided this was too perilous a risk.

With a stranger the possibility of rejection is daunting, but at least you can be safe in the knowledge that the pain of the slap will eventually lessen and you will probably never have to see her again.

The idea of being knocked back by a friend is so much worse – I imagined her aghast and appalled expression and the humiliation of being given the cheek-off.

I was still wrestling with this dilemma when we went up to bed.

When she briefly disappeared into the bathroom I hoped she would emerge scantily clad in lace lingerie – unfortunately this was not the case.

Unintentionally provocative in her baggy T-shirt and jogging bottoms, she smiled up from under her deliciously cute blonde fringe and we settled down for a night of chatting and TV watching.

At this point, I confessed my undying lust. Being charm personified, she rejected me in the nicest possible way citing a previously unmentioned boyfriend.

Sadly, I realised I wouldn’t break her resolve this time so I’m choosing to look on this as valuable groundwork for the future.

Next week: Sally Churchward’s My Life