Why do I feel bad for wanting my money back?

 Do you feel guilty when asking a friend to pay you back for something you covered for them? It’s awkward, isn’t it?
I have someone I paid for. They agreed to pay me later but never did. I never reminded them, and now it’s been too long for me even to bring it up. As a person who has lent money to a couple of people, one thing I have learnt is that people who do not pay you back think you do not really need the money back or have the ‘I will give it back later’ attitude. 

Here is the thing, when they come to borrow money they always have an excuse for why they are broke and promise you a timely payment in full within weeks or months, but be prepared to wait for years or even them blocking your number.
And this is how good people always willing to help sometimes just stop because they have had enough. But why does it feel embarrassing or awkward to want your money back? 

According to a life coach, there could be several reasons contributing significanty to the awkward factor, most of which can be avoided using clear communication, agreed upon and reasonable expectations in a non-judgmental manner:

Perception of pushiness or confrontation: You may feel awkward because you do not want to come across as a demanding loan shark first and friend second. Some people do not have much confrontational fibre woven into their DNA, yet it is perfectly fine to ask for their money back.
Concern for damaging relationships: The awkwardness may make you aware of the possibility that asking for your money back could cause immediate and potentially long-term and irreparable damage to the relationship you share with the borrower. The awkward factor increases when the borrower is a family member or years-long friend. 

Embarrassment for needing the money back: As our finances ebb and flow and life presents unexpected hard times, it is nice being there and helping out somebody you care about when they needed it. But at some point after helping them out, you may find yourself in the same position yet feel embarrassed to request the money back, feeling ashamed you need it urgently.

Uncertainty about asking: You may feel unsure about how to ask for what you are owed or maybe even experiencing anxiety. This can definitely make requesting payback uncomfortable and difficult and may even delay asking altogether.

It is important to remember that it is perfectly reasonable to ask for money you lent to someone with clear expectations of paying it back. Taking a confident, clear, non-judg-mental and respectful approach can make the process smoother and more comfortable for both parties.