It kind depends on the situation. I have money loaned out (still) to around 5 people and they never pay me back and I feel like crap when I finally ask. Pretty sad but I feel like I am doing something wrong asking for my money back. I have and still do purposely avoid certain people cause they OWE ME money. Sad!!!
If we were at a casino and a guy was short on cash cause he didnt bring enough then no problem on the spot but if he was broke and couldnt afford his lfifestyle and needed to 2k to pay for something then you have to ask how is he going to pay you back, it will be slowly meaning you will always be behind camping trips, nights out to the bar, gifts for his lady, bills, restaurant's, etc. Believe me I have got burned more then I can count.