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Dear Richard Madeley: My boyfriend might propose on Valentine’s – and I don’t know what to do

Richard Madeley
3 min read
Cartoon of a woman jumping out of a gondola into a canal as a man on bended knee proposes
‘I’m not horrified by the idea, but if he does ask me in some sort of set-piece – in a gondola or something – I’m worried I’ll feel cornered and say no’ - Ron Number

Dear Richard,

After a couple of terrible Valentine’s Day dinners, this year my boyfriend and I have booked to go to Venice for a few days.

I was using his computer yesterday and I happened to notice that all the banner ads were for jewellery, and of course I have concluded that he’s going to propose. I’m not horrified by the idea, but if he does ask me in some sort of set-piece – in a gondola or something – I’m worried I’ll feel cornered and say no, and then he’ll be really hurt.

However, I’m simultaneously worried that if the trip comes and goes and there’s no ring, I’ll feel strangely disappointed.

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I realise this is absurd. But we’ve always tried to have an equal and non-patriarchal relationship and this whole thing of me just twiddling my thumbs and waiting for the man to act really grates on me.

Should I talk to him ahead of the trip? Of course it’s a leap year this year, so traditionally I could ask him at the end of the month. In spite of myself I quite like the idea that he might be planning a big gesture – I just don’t want to feel bullied by that gesture, but equally I don’t want to throw it back in his face. Any thoughts?

— Maggie, London NW6

Dear Maggie,

I guess the central problem for you here is that you can’t unsee what you’ve seen. And, clearly, you can’t stop thinking about it, either.

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Now look. He may simply have been browsing sites on his laptop because he’s thinking about buying you something nice and sparkly for Valentine’s Day. I don’t quite understand why you’ve leapt to the conclusion that he’s going to propose.

But let us, for the sake of argument, accept that you’re right. Why would that make you feel ‘cornered’, Maggie? Still less ‘bullied’?

Surely it’s simply a fork in the road; a moment of decision. If he’s intending to present you with a sparkler, whether it’s on the Bridge of Sighs or in the departure lounge at Luton Airport, he’s clearly made his. He’s not ‘bullying’ you – he’s asking you a question. And if he does ask, and you say no – well, he’d have to respect that, wouldn’t he?

You talk about ‘twiddling your thumbs and waiting for the man to act’. I get that, Maggie; really, I do. So here’s a suggestion. Buy him a ring and propose to him. Just try that idea on for size…

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

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