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06 Sept 2025

Dear Fiona: I fancy my younger colleague but he’s ignoring my messages – should I ask him out again?

Dear Fiona: I fancy my younger colleague but he’s ignoring my messages – should I ask him out again?

The problem…

“There’s a bloke at work I really fancy. He’s 37 and I’m 55. Age doesn’t bother me, although I’m not sure about him as we haven’t spoken about age. Anyway, I took the bull by the horns and just asked if he was single. He said yes, so we exchanged numbers and said we’d go for a drink. Since then, I’ve asked him twice when he’s taking me for coffee, but he doesn’t get back to me.

“I made him a Christmas card, but he didn’t say it was nice or anything. I’ve phoned him a few times, but he doesn’t pick up (well he did but only once). When we talk at work, he is nice to me and we laugh, and I’ve made him cakes and cheesecake, which I know he likes.

“Do I ask him face-to-face one more time if he’s going for a chat and drink with me? Do I write him a note expressing how much I like him, and ask him to just give it a chance to get to know each other? Or do I just try to forget him, which is hard as I’ve never fancied anyone like this before.

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“I split from my ex five years ago – after I got breast cancer and he went off with a someone 10 years younger than him. As a result, I was in a bad place for a while, but five years on I feel I’ve found someone I really like and would like to get to know more. I’ve never in my life asked a bloke if he’s single or asked for his number or even for a drink, so I thought it’s time to start putting me first and take the chance, not that it’s worked yet sadly.

“I think deep down, I’m just chasing nothing and wasting my time, but I’m holding on to a little hope he will say yes one day and put a big smile on my face. Am I living in a fantasy world?”

Fiona says…

“You’ve come a long way in five years. You’ve coped with breast cancer and all the ramifications of that. You’ve coped with separation from your former partner when you really needed him, and you’ve coped with him going off with a younger woman. You’re clearly a strong person, who can stand up for herself and hold her own in difficult situations.

“This man at work is clearly polite, but I think you need to face the fact that he’s being just that and trying to avoid a difficult situation. You are making moves on a colleague, and he’s trying to avoid a difficult work situation. Hence, in the workplace, he’s responding politely, giving you his number, being nice to you, laughing and joking. Away from work though, he’s not picking up your calls and is trying to avoid commenting on anything personal – like the card you made him.

“Putting you first is exactly the right thing to do after all you’ve been through. And asking someone for their number or asking them out is fine. It’s assertive and that’s a good thing. To keep doing it though – when they are trying to show they don’t want to take things further – is not such a good thing.

“Having a relationship with someone at work is always tricky at the best of times. If things go wrong, it can sour working relationships not just for you but for other colleagues too. You’ve proved you’re more than capable of building a life for yourself again, so why not look outside the circle you’re currently in for new and different people? Take up new activities where you meet new people; go to different places; have a variety of experiences – they will all increase your chances of meeting people you might like.”

If you have a problem you need help with, email Fiona by writing to help@askfiona.net for advice. All letters are treated in complete confidence and, to protect this privacy, Fiona is unable to pass on your messages to other readers. Fiona regrets that she cannot enter into personal correspondence.

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