Something for the ladies # 25

Ladies: If there's ever been anything about men you've wanted to know but were afraid to ask, or wanted a male viewpoint on a certain relationship niggle you're going through, drop an email to us at todger dot talk @ googlemail dot com. We shall pick one out and answer it to the best of our capabilities.

This week's question...

Anonymous writes: Hello lads,

I run my own business and I've recently sought the advice of a fellow business owner, who has been very generous with his time and given me a great deal of financial advice. I want our relationship to be more than professional, but I don't know how to subtly find out is he's single (there are no obvious signs like a ring). All of our correspondence is very professional and via email, and I desperately want to break down that barrier without making a fool out of myself.

When we first met at a networking event he looked over at me three times while he was talking to someone else, so I know that there is some degree of interest on his part. I feel a sense of urgency with this before our relationship enters a "strictly professional zone". I think so highly of him that I would be happy just being his friend if he didn't feel the same way that I do, so I know I need to act carefully. I'm 25 and he's 31, and I think he likes to see himself as my mentor.

Any bright ideas please?

Sam says: OK, there is some serious strategising that needs to happen here. Firstly, you need to remember that when a guy meets a younger girl in a business context we tend to lean on the side of caution. There is nothing worse than getting a sexual harassment suit from a younger woman to make your life a misery. What this means is that you need to discreetly take the lead and make it clear you are interested.

Step 1 – Gather intelligence

Do you have any mutual professional contacts? If so, discreetly ask if he is married or has a girlfriend. If you don't have any, then next time you see him as something like 'Is your wife involved in business as well?' You'll quickly find out whether he is single or not.

Step 2 – Get him out of the business strait-jacket

It’s crucial that you meet up outside a professional context. The easiest way to do this is to ask if you can meet up for a drink after work for him to give you some advice on business topic X. A bar is what anthropologists call a 'liminal' space – a place where the rules of outside society are temporarily suspended. Translation, you are allowed to flirt with business colleagues there. When you get there for the drink as quickly as possible move off business onto personal topics. Also, flirt like crazy with him. The more flirting the better.

Step 3 – Get a bit sozzled and have a snog

Alcohol plays a very important role – it allows you to do things you wouldn't otherwise try and get away with it. I would suggest when going out to drinks aim to get a bit sozzled and then at the end of the night, when saying goodbye, rather than offering your cheek, tip you head to one side, lean in towards his lips and let him close the deal. If it all goes wrong you can always blame drinking a bit too much booze. If it goes right, Hurrah!

‘Mr Sex’ says: Right then, I’m going to be the angel on your shoulders and hit you off with the other side of the coin; yes, he was checking you out at that networking meeting, mainly because a) he’s male and b) those things are boring as fuck. Personally, if I were at something like that and a balloon with swastikas drawn on it with marker pen floated in the room, I’d be thinking about shagging the arse off it, just to alleviate the sheer boredom of it all.

The problem is, this is still a work relationship, even if you’re self-employed, and there’s still a degree of professionalism needed – after all, if it goes horribly tits-up, it’s going to have a serious effect on your working relationship. At best, it’s going to tip the balance decisively in his favour (after all, if he sees you as your mentor, he already feels he has a degree of power). At worst, it’s going to break it completely.

So my advice to you is to follow Sam’s advice, but add Step 0 – be a bit more chatty in your e-mails. Initiate a bit of random banter with a PS, or something like that, so you get to know him a lot better whilst basking in the safety of hiding behind a monitor. The benefits of this are that you can subtly steer the conversation in the direction you want without committing to anything, and having the time to think about what he’s said and what you want to say in return. All the info you need to know will be revealed in time, and you’ll have a far better idea where you stand without risking your professional relationship or making an arse of yourself.

Readers of TT – comment!