I've been friends with this person for years. She's really lovely, supportive and good fun and most of the time this isn't a problem but I am feeling myself starting to feel resentful.
In a nutshell, she went through a really bad break-up around the same time I broke up with my DH. She was in a real financial mess and I helped her out a bit financially. I knew I wouldn't get the money back and was very clear after I had helped her, "this is a one-off and I can't afford to help you out more than this". It was to the tune of £1,000 and she paid me back £500.
Moving on to now, she's in a much better paid job (I'm estimating £50k), all children grown up. One is at home, paying housekeeping and the others are independent. I'm in quite a low paying job, have 2 kids at home but get maintenance from ex and have a bit extra income from money I invested over the years so our actual incomes are probably comparable over a month.
However, occasionally when we go out or when it involves paying for tickets in advance, she will say things like "I'm your poor friend" and go on about how little money she has compared to me. I feel like she expects me to say, it's okay and I don't need the money when in actual fact I do need the money.
I suspect she's done this with another mutual friend, as although we're all really close, said mutual friend now refuses to book seats in advance where an upfront payment is required.
She currently owes me £30 for tickets I booked for a Christmas event we all wanted to go to and I dread asking for it because I know what the answer will be. How would you handle this?