Having a hard time spending

Money is important to me. I am a saver and love knowing that I have money on my bank account. I do, however, have a hard time spending money. I buy things only if I absolutely have to.

I am spending more time looking for a discount vs. using that time to make more $. Buying expensive gifts and giving $ to people who are not my super close friends or immediate family is hard, too.

How can I learn to give with generosity and without feeling regret or being unwilling to give?