Dear Richard Madeley: How do I approach the handsome man at work without upsetting my colleague?

Dear Richard,

I volunteer in a National Trust property and I’ve become friendly with another woman who does the same. I am unattached and keen to find a partner. There is a very handsome, funny man, a little younger than we are, who is working on a conservation project in the house and has sought us out for coffee several times.

My friend and I both think that he may be attracted to one of us. He is always so cheerful and charming and I would definitely say there’s a ‘twinkle’ there but I don’t know whether it’s directed to one or other (or both) of us, or whether he is even available. I would really like to ask him out but don’t know when I could do it as my co-worker is always there. Should I try to find out more about his situation from a colleague of his, or approach him when he’s working? Also, I don’t want to upset my friend if she’s interested in him, too.

 — Olivia, Suffolk

Dear Olivia,

Well, if I was looking for a rom-com plot line, your letter would have just provided me with it! But this is real life – so what to do? I’m pretty clear, and actually I don’t think you’ll be all that surprised by my advice.

Firstly, talk to your friend. You say you don’t want to go behind her back – so don’t! Tell her up front that you want to ask this guy out. If she bristles and says that’s exactly what SHE was planning to do, there’s a tried and trusted solution to the impasse – flip a coin! Make it best of three.

I think it could be quite exciting!

Now, if he’s actually with someone else and is simply being a bit of a worky-flirty, there’ll be no harm done and you can both scan the horizon for other opportunities. But if he’s free and available, whoever wins the toss will either get the ‘yes’ from him or be politely knocked back – and that’ll leave the way clear for the loser to have a crack.

But try and treat this whole scenario as a bit of fun, Olivia. And let my readers and me know what transpires! We all love a happy ending…

You can find more of Richard Madeley’s advice here or submit your own dilemma below.

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