And what if it comes across like I am forcing myself on him? I am quite a bit older than him. He doesn't know exactly how much but he might do the math and have a pretty good guess. I'm not sure how to approach it without being overly intimidating. I'm not sure I've really asked someone out before. Guys are usually scared off or angry about how I approach them.

About what I have to lose...if the rejection is respectful and not intentionally hurtful, just confidence. If he is cruel about it like what's happened in the past...I probably won't pursue a man again. It would do a lot of damage to me.