How do I get a guy to ask me out without seeming a little desperate?
Why do you want him to ask you out when you can just ask him out yourself? This isn’t about seeming desperate. If you like someone, go and tell the person that. Don’t expect him to be a mind reader. This doesn’t have to be about a relationship either. Just start with coffee and get to know him better first.
I dated a girl for four years, and we ended up splitting because I moved to the Middle East. I worked there for a few years and returned earlier this year. We both dated other people during the time I was away. She knows I’m back now though, and recently sent me a message asking if I wanted to meet up. I don’t know if this is a good idea, because I have changed a lot as a person. I’m sure she has changed too. I don’t want to get into a relationship with someone just because we used to have one years ago. How do I do this without hurting her feelings? She is still someone I think of as special in my life, and I would like to continue being friends with her, if possible. This is really making things awkward for me because I would like to date other women and I need to move on and put this behind me in order to be able to do that. What do you suggest I do?
Relax, hotshot; aren’t you jumping the gun here a little? You’re assuming she wants to get into a relationship before you take the trouble of meeting her? You are one presumptuous man. Maybe she wants to introduce you to her fiance, so relax and meet her if, as you say, she is someone special in your life. Also, try not to overthink this too much. Take it as it comes. No one’s forcing you to get into a relationship with anyone at gunpoint.