Should I be upset or was I thoughtless?

Bit of a faux pas but if I'd been the friend (I'm 68) I would've graciously accepted the card and not said anything.

You meant well but got it wrong, it sounds like she wasn’t so much offended as confused about why you had basically given her the wrong card. She was nice to you on the evening so sounds like there are no hard feelings. Just send her a message saying sorry about the card and explain your thought process e.g. that she is “retiring” from that particular career (or whatever she’s doing) but you know she’s not completely retiring and in hindsight you should’ve bought a good luck card

So what made you buy a retirement card then?

Well it says in the OP the friend is 66

Don't hate yourself, we all slip up socially sometimes. She could have just said "thanks for the card, although I don't consider myself retired," and moved on from it rather than making a fuss and letting you take the card back. Your other friend wasn't being particularly helpful in taking your quip about bus passes seriously when you were just trying to lighten the mood. Sounds like everyone's a bit tetchy in your group at the moment. I'd think no more of it and hope they're in a better mood next time you see them.

What makes you think she’s 66?!

No she shouldn’t. Sounds like the way she reacted was very low level and she then went out of her way to be friendly to the OP, I assume to reassure the OP that she didn’t bear a grudge. But firmly pointing out something really quite insensitive is perfectly appropriate in the circumstances. No simpering tinkly laugh required.

God save us from the Mumsnet tinkly laugh. It really isn't the answer to everything (or indeed, anything) you know!!

The other woman should have had the maturity (however old she is) to know that OP would not have bought her a card and gone out with her to deliberately upset her. She had no right to take a sledgehammer to the otherwise nice vibe. A tinkly laugh and 'don't forget I'm not actually retiring just yet' would have done the trick perfectly.

can you seriously not put yourself in the position of someone who is embarking on a new career and momentarily feels she is being put into a “knackered old woman” box by someone she considered a friend?

Exactly! Retraining and getting a new job is daunting at any age. As middle aged person it can be horrific, mainly because of the stereotyping you see on this thread. Having your friends assume that you’re retiring just makes it 100% worse. To her it will seem that you’ve not listened to her plans and/ or completely minimised them.

As well as being useless to the job market, women over 60 should apparently be grateful for any old tut in an envelope, however inappropriate.

This is a really fucked up way to manage relationships with people.

Some of you could learn a lot from the op and her hobby friend. Op said something that upset her. Friend raised it. Op has taken it on board. This is how normal relationships function, I promise you. Things like this really don't need to be friendship ending.

That’s what I can’t work out, OP clearly knew she wasn’t retiring yet still purchased a retirement card!

Why have you decided she’s a passive aggressive arsehole? Totally bizarre! The friend made it very clear she wasn’t retiring, and OP got her a retirement card anyway based on her age, despite knowing the friend had corrected others that she wasn’t retiring.

Why did you give her a retirement card then 😂

I'm amazed that some people can't see why the woman was upset. She, by the op's own admission, had made it perfectly clear that she was leaving her job due to a restructure (often an unpleasant thing to go through as an employee, it usually means you've lost your job) and retraining to find another one. Op KNEW this but allowed the fact that this lady was 66 to override that fact and buy her a retirement card. When the woman pointed out the error she compounded it by talking about bus passes.

It really was a foot in mouth and then keep digging scenario. I sympathise with the poor op who clearly feels like crap about it today but the woman on the receiving end did nothing wrong by pointing out she wasn't actually retiring. Imagine if she hadn't? Every time she saw the op they'd be having an awkward conversation where the op asks her 'how is retirement going?'. I'd rather be told I've messed up as soon as possible than that!

It’s just reinforcing a lazy stereotype they all women over 60 are no use in the labour market and should be grateful to retire and spend the day watching TV and visiting garden centres. Whereas in fact lots of women over 60 either do amazing things in their careers or retrain. And most of us will still be working at that age, the way the economy is going

I think it was a bit of subconscious stereotyping from the OP, yes, and I think this is exactly the nerve the OP touched with this woman. I certainly don’t think it was deliberate or malicious but there was a bit of a lack of thought and empathy.

People on this thread saying she was “dickish” are being a bit obtuse. Older women face so much prejudice at work and in society: can you seriously not put yourself in the position of someone who is embarking on a new career and momentarily feels she is being put into a “knackered old woman” box by someone she considered a friend?

So passive aggressive then? Jeez what an insufferable arsehole. She might be retirement age but she clearly hasn’t grown up. Don’t give it a moment’s thought op. You did a nice thing. She’s the one with issues.

Are you serious? The woman wasn’t retiring. She was going to undertake some further study, possibly after being made redundant, and then going back to work. The OP acknowledges she was always clear about this.

Would you be happy if a friend bought you a “welcome to your new home” card on your birthday? And then made it worse with a tactless comment like “oh yes, I forgot you rent, maybe by next birthday you’ll have bought a house, I’ll give it back then…”

This is exactly why you can't extrapolate how you, I, or anybody else would feel about the same comment. Circumstances and perspectives differ.

‘Of course’ - so why give her a retirement card when you knew she was NOT retiring and had previously corrected people?

I retired mid50s - lucky me
I was thrilled
Never been busier since ...

I get she must have been surprised to get a retirement card if she’s told you all she is returning to work after the course, but it was clearly just a faux pas on your part. She obviously realised that was the case from your reaction, hence being extra nice after. She probably wishes she hadn’t made such an obvious fuss, as much as you wish you’d got a different card. Just message and say you don’t know what you were thinking - I’m sure you will laugh about this in years to come @HelloDenise

Well, I'm 58, so I would be bemused more than anything...

If I was insulted, it would be because I know that gaining weight is a terrible crime for a woman that it is deemed rude to draw attention to.

Retirement isn't. You are making the assumption that retiring is deemed to be worthy of insult. I disagree.

You sound a total delight.