A girl or woman who is in a relationship with a guy does not hang out, one-on-one, with other single guys. That is what is normal and appropriate. If she wants to continue a friendship with a male, she might invite him, along with other guests, to stop by on Christmas eve to join herself and her significant other for a drink. She might invite him to stop by for a hamburger when she and her sig. other are grilling in the backyard and hosting a get-together for family/friends. If you're not too interested in hanging out with her boyfriend, as well as her, in a group social setting, then your days of spending time with her are over. It is not appropriate for her to be meeting up with you to spend time alone with you, just hanging out. That's what is called "a date." She is not available to date you or any other guy. She's in a relationship. Her boyfriend would have every right to object to her meeting any guy to "hang out" alone with him. Even if she were not involved with someone, she is not going to want to "hang out" one-on-one with any guy she is not romantically interested in.

I know some people like to talk about how it's just fine for a person to have friends who are of the opposite gender and meet up with them to do stuff or just hang out. In reality, that's not how normal human socialization works. Cross-gender friendships usually get maintained by the 2 friends seeing each other in group social settings. If they telephone each other, it's for one to invite the other to a get-together that will be attended by a group of people. You wanting to be alone with her is you wanting to "date" her because you have a crush on her. Stop it. She doesn't want to date you. Calling it "hanging out" doesn't change the reality. You are using the fact that she owes you money as an excuse to push yourself on her to a degree that makes her uncomfortable. That is not how a gentleman acts. She's trying to avoid being unpleasant toward you. Eventually, she is going to resent and dislike you.

You are using one of the oldest tricks in the book of how men get access to women. You see a woman you're attracted to who is in tough straits financially. You provide her with some money. Then you take advantage of her indebtedness by hovering around her and looking for openings to make a move on her. Because she owes you money, she is inhibited from just bluntly blocking your advances. So she acts pleased that you want to be "friends" with her, while she is really uncomfortable with your attention. She knows perfectly well that you "have a crush" on her, and she does not want that kind of attention from you. Since you won't "take a hint" and back off, she feels forced to keep up this "play-acting" about how you two are buddies and need to get together. This little drama has been going on for thousands of years between men and women. It's the reason that, traditionally, moms teach their daughters not to accept money or expensive gifts from guys they don't want to become overly entangled with.

This gal was wrong to accept money from you. It came with strings. She feels she has to be ever so nice to you because of the money. She doesn't really want to have to pay it back. She would love for you to say, "Consider it a gift, and don't worry about paying it back."

You, on the other hand, would probably be willing to make the money a gift -- if you were getting something in exchange . . . like a certain amount of attention from her . . . which you are not getting. Like I said above, this is one of the oldest strategies employed by men to get access to women. If the woman doesn't reciprocate with the attention the man wants to get from her, the man tends to become resentful. Some men in this situation become so angry that they even physically assault the woman. I don't see you doing anything like that. But you are trying to hover around her more than she wants. Men who do that run the risk of being considered creepy.

If you watch "Judge Judy" or similar court shows on TV, you will see lots of cases where a man who loaned a woman money is suing to get it back. Always it's the same scenario: the man had hoped for a continuing relationship with the gal. He was ever so patient about waiting to get back the money. Then, once that hope for the woman's attention died, he wanted that money back. It's a pathetic situation for a man to put himself in. You can't buy a woman's attention.

Actually, I take that back. You can buy a woman's attention. There are women in third world countries who make those kinds of arrangements with financially secure American men. They used to be called "mail-ordered brides." Once in a while, those arrangements probably work out okay. Here's an article on the subject: "Mail Order Brides" Still Exist | Psychology Today

You've been passing out money to people, telling yourself that it's just because you "like to help people." But then you're disappointed at what you get back. It's time to get honest with yourself and recognize that you want to receive, as well as give. There's nothing wrong with that. Save your money to "invest" in a person who is offering what you're looking for. There's no shortage of single young women in the world who are looking for men, especially a nice, young man with a job and money in the bank. Also, recognize that you need someone for more than just "to hang out with." After all, you're human. That's a basic human need. Go at it more directly, and stop wasting your time, effort . . . and money.

As for the money you lent to this "friend," I'ld advise you to just write it off and chalk it up as an educational experience. That would help give you some peace of mind. Then: Let go. You don't have to call her up and make an announcement or a speech. Just stop trying to corner her into a date. Then see what happens. Maybe she'll call you up one day and invite you to a backyard barbeque. That would be appropriate. She's way more likely to do that, if you tell her to forget about the money. One day she might introduce you to a single gal who's looking to meet a guy. Leave her free to offer the level of friendship she's comfortable with.