Let go.

It's not the money you really want. You want her. She's not available. Stop trying to recreate what you experienced two summers ago. Let go.

Of course she'ld like to pay you back. No one enjoys feeling indebted. No one enjoys accepting a handout. But she is struggling just to get by. So let the money go. Don't make another announcement that you want to gift it. Just stop bringing it up. Stop thinking about it. One minute you're worried about not getting it back. Next minute you say you're not concerned it. Forget about it. Close the book on it.

Then be a gentleman. Leave the ball in her court. See what she does. See what she initiates. If she contacts you and wants to plan a hike with you, fine. I don't think she will. Basically a hike with her is "a date." She's trying to wind down this involvement with you. But you're hanging on, wishing and hoping. You're pouring all this mental energy into wanting to recapture a closeness that you experienced a few summers ago that felt "awesome" to you. It's not going to happen. She feels she can't tell you that because she owes you money.

She feels she "owes" you. You feel she "owes" you. That's the thread that keeps alive the connection between you. You can't build or sustain friendship on that. Forget it.

This woman does not make you feel alone. You are alone. You are alone because you want a relationship that is not available to you. And you will not accept that reality. She doesn't want to spend time alone with you. She doesn't really want to go hiking or have coffee with you. She says she does because she feels uncomfortable not saying that because you did a nice, big favor for her (the loan) and she feels trapped into acting more interested in you than she really wants to keep up. How many more months are you planning to keep this game going.

Let go. Move on. You need friends and you need a girlfriend. She doesn't really want to be either to you. You're going to have to look elsewhere for friendship and for love. Start now.