I'm so sorry you're hurting so much, Skulls&Crossbones I'd suggest to just go for it and see how it goes! Ask him out! I agree with what all the others have already wisely said better than I ever could! I completely agree with what divine1966 has already wisely said! Try to understand what are his hobbies and what would he like to do with you! Perhaps you could start from there! Just try to be yourself! I understand why you'd feel shy! That's perfectly normal! I'm so sorry you've been through such an horrible relationship! Please don't let that dictate how you should live your life! There's nothing wrong with asking out a man and taking decision! The age difference is not that big in my opinion and it's perfectly acceptable! If he has a problem, I'm sure he'll let you know! I'd suggest to just ask him out and see how it goes from there. Try not to think too much about what may go wrong, otherwise you'll feel stuck! Just go for it! Perhaps you could try to do some meditation exercises before asking him out! I believe there are many great videos on YouTube about all of this! As for discovering yourself and experimenting, you're doing that already! By asking out other people and getting to know them, you're already in your path to self-discovery! Please recognize that and be proud of yourself! I hope you'll decide to ask him out! If it's not, that's perfectly ok! Perhaps things will get better next time! Just keep trying and NEVER give up! That's the most important thing that you can do! Just try to do your best! That's all you can do after all and it's more than enough! Be yourself, keep trying and keep fighting, Skulls&Crossbones! You're a strong, wonderful person! You're awesome! You're strong! You're a warrior! I believe in you! We all believe in you! We're all rooting for you! We're all cheering you on! Keep fighting! I'm so sorry you have to deal with all of this, Skulls&Crossbones! Sending many hugs to you, Skulls&Crossbones!