Should I ask for this money back?

[Blownspeakersandvolcanos]

I worked bank holiday and as a treat we ordered food into the office. You had to pay by card and so I paid and everyone gave me cash but one person.

This person I see as a good friend.

But this behaviour is very typical of her. Its always the odd £5 or £10 that I never actually see again. Not a lot of money but it sure adds up.

I still have not seen the money for this food and usually I'd let it go but I feel I need to stop being such a bloody doormat.

If she is purposely not repaying you then you should definitely ask for it back.

If she has genuinely forgotten about it then she would want you to ask for it back.

Yes, ask for it.
Hey, remember the food we had last weekend, you owe me x amount. Ta.

Because I'm a bloody mouse that hates awkwardly asking for money back sad

So don't ask awkwardly, there is absolutely no need for awkwardness. All you need is a breezy word along the lines of "Oh, by the way, could you let me have that money today, then I won't have to go to the cashpoint" or something similar.

Definitely ask in a non awkward way. Along the lines of "hey, have you got the money from lunch the other day? I forgot my purse and I need to pick up bread and milk on the way home".
If she doesn't give you it, I would then bring it up in front of other colleagues and not put it on your card again.

Do you know why you find it awkward to ask for the money back? Are you more worried what your friend will think of you or more worried that you will make her feel awkward?

Sidle up behind her saying "Where's my money, man", in a whispery sinister voice.

I wouldn't stump up for work related stuff anymore, anyway. You've had your turn, let someone else take their's.

Otherwise people will start to see it as your job to do it all the time.