No bravery required, just good manners. And every time you do it, it'll get easier and easier. Putting the focus on other men and getting a nice response from them will boost your self confidence enormously. It will help you to feel stable enough to disengage from Mr Downer. Caught, first of all, you are NOT caught. You are only 25. You have so much before you and you don't have to settle for this guy's crumbs. Trust me and everyone, this is NOT it. Face the fear because it is not grounded in reality. If you don't love him (great insight), don't hang in the disappointment cycle for fear that there is nothing else out there. There is. It is you. Self indulgence and self-esteem doesn't cost money. It takes work. Congratulations on finishing your masters. That is fabulous and took work (and money) so you can break the cycle with the guy. Sweetie, I'm 53 and barely out of the woods with regards to the disappointment cycle with men. I have a 23 yro daughter who may be in the same lather, rinse repeat cycle with men. I wish I could tell her just flush. If they don't treat you with love, trust, and respect, flush. So if it is any consolation, even at 53 there are plenty of guys. Self-esteem doesn't cost money otherwise we'd all be buying some. It costs work and you are well on your way. If Nat would allow it, I'd like to