lara asks :

I have meet a guy at work who i think is quiet sweet & charming & would really like to start dating him, however I have some concerns. firstly he sees me as more of a friend, and when ever i ask "hypathetical questions" about what he would do if he was a guy in a situation he just shrugs them off & changes the subject but then in 15mins time he will start playing along & get flirty with me.
I dont want to ask him out only for him to reject me & make being at work together difficult. Also my dad works with us & I know he probably wouldnt approve of me dating him. my friends arent very good with advice so i need to know what the best corse of action to take

Yin replies

I’m sure you’ve come across Men Are From Mars, Women Are From Venus, by Dr John Gray? Well, it’s an accepted truth that men really don’t react well to subtle mind games – or anything beyond black and white really.
If he’s playing along with your hypothetical situations, he’s probably just having fun and thinks nothing more of it, and is enjoying the attention. Is he flirting or is he just being friendly?
Remember that some guys have a naturally flirtatious character and mean nothing by it. Ladies, too, of course. If you’re hoping he’s flirting with you, you’ll probably look for signs.
But what is it about him that you think your dad wouldn’t approve of? Is it something that you know, deep down, isn’t right for you? Are you using your dad’s potential disapproval as an excuse for not sticking your neck out and asking him out?
Or are you just aware that he’s probably a bit of a lad in your dad’s eyes and you wouldn’t want the embarrassment of being rejected, especially if your dad found out? I’d recommend trying to orchestrate some kind of social situation out of work that he’s guaranteed to go to, somewhere you can see how you get on with him out of work, and see how much attention he gives you.
Don’t jump, don’t play games, but try to buy yourself some more time and situations for picking up some kind of clues about how he feels about you.

Yang replies

Wait a minute – before you even think about asking him out, remember how you started your letter. ‘I’d really like to start dating him.’ Does he even figure in this situation?
I mean, it’s all very well you saying you want to start dating him but it only works if he feels the same and I’m sorry but as he’s playing with you already, you have to wonder if he’s just going to toy with your emotions whether you’re just friends, you’re flirting or your dating.
He sounds like a player, Lara, and I think you should be cautious. With someone like this, let him do the running. Don’t even think about setting yourself up for a fall. I’m not saying he doesn’t fancy you – he just sounds like the kind of guy who needs to do the asking.