Dear Richard: ‘I’m attracted to a work colleague but she’s older than (and senior to) me’

Dear Richard,

There’s a woman at work I would really like to get to know better but I don’t know the best way to approach her.

We don’t work closely together but she is at a higher level than me; she is also I would guess about five years older (I am 25).

I feel like office romances happen quite a lot at our work and no one seems bothered. Our office is quite sociable, with lots of team drinks and activities. When these activities resumed during gaps in the pandemic, we had some really friendly conversations, which I thought might be mildly flirty – but I don’t know how to take the first step.

I have been doing online dating for a couple of years without much success and I worry about getting it wrong. I also worry that it’s automatically a bad idea to ask a co-worker out. Can you advise me?

– KB, Leeds

Dear KB,

Well you’ve certainly stumbled into the right store here! My wife Judy and I met at the office and there was a similar age difference, too. So what? Five summers might have mattered when you were 13 and your would-be inamorata was 18, but now it’s completely irrelevant. Stop worrying about it.

Similarly, the fact that you work together is neither here nor there. Lots of couples first set eyes on each other at the office watercooler. It’s a perfectly legitimate way to meet. There might be some issues if there was a direct hierarchical relationship between you, but you say that’s not the case; in general, the stuffy days of workplace romances being puritanically proscribed are long gone.

So that just leaves us with your one remaining concern – “getting it wrong”. Well, it may be a cliché to say that faint heart never won a fair lady, but like most cliches there’s a core truth in there. So step up to the plate, KB, and ask her out!

You have absolutely nothing to lose, and everything to gain. In my case, it was a 35-year marriage, four children and three grandchildren – so be careful what you wish for!


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