Question: Should I ask this guy out? The problems are: 1) he lives rather far from me 50 miles +, same state, probably 2 hour + drive among us Though this may or may not seem like a big deal to all, but it can if I ask him out? I mean how will we see each other often? Or should I even worry about that now?? 2) I may not be his type. He's one of those adrenaline junkies and I'm more of a mature woman who also likes adventures, but he's like a surfer dude(to give an idea). 3) Age - we are a lot a a part (I won't say how much, but think Demi Moore and Ashton Kutcher) - yes I'm the older woman. (These guys are my age ranger I prefer - please no criticism on this and stay focused on replying to my situation.) 4) He may not remember me. I met him briefly last week and it was just for an event. I saw him and liked him, but I was one of many of his adventures he had to share with. I tried emailing the adventures thing I did, and they gave me his contact, but he won't remember me unless there was some sort of photo but wouldn't it seem weird to send a photo of me. 5) I may not be able to show my face again, if I ever someday want to go back to the event. He may (or may not) remember me. Anyway, I just wanted to briefly said hi, and tell him what a wonderful time I had shared with him, not expecting much, but should I even bother? I don't want to get hurt or ruin a wonderful experience I shared with him. Should I just let this go? Does anyone out there believe in taking a chance or is it best to just dream away wishing it happened and move on? Think about the strangers you meet in life that you wish you knew. Would it be strange for you if an email came out of nowhere or you least expect and someone asked you out? Would you find that strange or flattering? How much would you remember someone if they described a certain incident that may trigger a memory? Please it would be nice if guys answers this. I'd appreciate it and if all answers answered. Need your help!