To tell friend how I feel about lending money

[pupsiecola]

My best friend has asked me for a loan to see her through until pay day (150 quid). This has happened about 6 times in the last 12. We also leant her 500 quid 2 years ago. Last month she paid back 50. The rest is outstanding. I know other people have leant them a lot of money too.

Her DH has MH issues. She has a really really tough life. She works full-time and has a DD. They have struggled financially since he had a breakdown around 15 years ago. He's not really worked since.

She has started a relationship with someone at work who also has MH issues. I am worried about her because whilst I don't judge her (and actually think she deserves some fun and a bit of happiness) he seems to be bring far more problems than he's worth (he is single, but much much younger).

Anyway, I always lend her the money when she asks, without question. She always pays the short term stuff back. The 500 I have almost written off.

I have two issues:-

1. Since getting involved with this guy at work I feel I don't hear from her as much and it's always me who initiates contact. But I know she is very busy at work etc. and I get that friendship is give and take in terms of effort put in. Only thing here is I do feel a bit taken for granted. Eg today I wake up to a chatty (but apologetic) text asking if it's possible to borrow the 150.
   

1. I don't think she is careful with money. For example she bought her daughter a pen for a fiver the other week! But she bought her the same pen in a different colour a few weeks ago. She bought her man friend a funny and pointless game for 20 quid last time we were together (2 weeks ago). Now, again I try not to judge. She works hard and it's up to her what she spends her money on. But it does make me feel a bit resentful when she then doesn't have enough money to last the month.
   

We are in the process of buying a house. We could really do with the 450 quid back. And whilst I could lend her the 150 and probably will as I love her and don't want her to have this stress, I do feel upset and I do actually feel resentment building. I am worried I will tell her how I feel about it, and it will ruin our friendship.

WWYD please?

[pupsiecola]

Thanks for the suggestion sidthesausage but that would def be the end of the friendship I think! She is very defensive about not being able to manage etc. It's a subject that is very tricky to navigate, and only gets raised when she needs to borrow money. It would offend her greatly. Plus she would think I was bonkers for thinking she actually has time to sit and read a book!