LW1: This guy is either a wimp like Amy suggested, or your lady friend is ambivalent. It really doesn't matter which. Personally, if the woman's reply is anything other than "yes," I don't bother a second time. "We'll see", "why?", "maybe I dunno", and "it would be weird" are all the same as NO. Women are always trying to "let guys down easy." I suppose that's better than being blunt, but truthfully I am a little disgusted by both the LW and by the object of his affection - he needs to ask for what he wants, and if it isn't forthcoming, immediately move on to greener pastures, not hang around and be "too available" like he's doing with the silly earring gifts. He makes it too easy for her - what woman would want a guy that she could have any old time she likes? As for her, a polite but firm "no thanks" would have been far better than the noncommittal responses she gave him over and over. If she isn't interested in some guy who is pursuing her, she needs to reject him in a way that is both polite and firm - letting him know that she's flattered by his interest, but simply not interested...and definitely not any kind of answer that would encourage him to keep trying. Amy is absolutely right. This guy needs to grow a pair and stop being so nice. He reminds me of a friend of mine who spent years pining over this girl he went to high school with, and he even got her to go out with him once. But she was so weirded-out by his obsessiveness and pseudo-romance and "trying too hard" that she eventually got turned off and told him to hit the road. (She was always nice to ME, though.) If you like a woman, ask her to lunch or coffee or a concert or whatever, but don't pussyfoot around. Women, it seems, respect a man who is driven, assertive (but not pushy), and knows what he wants. Come on ladies, you know I'm right.

LW2: He's asexual? Fine. I'm sure lots of women out there are tired of men who are only after one thing. His situation is tricky, because it isn't an appropriate first-date topic of conversation, but it also is something he should disclose before a relationship gets too involved. I'd say he ought to mention it the very first time the subject of sex comes up - and wait for her to bring it up - no matter what the context. Amy is right though - even if he is content to live like this, he still should double-check that there isn't some underlying, physical medical problem. By the way, a "eunuch" is a man who has been castrated entirely, not one who simply has no interest in sex. He's misusing the word, and if he goes around saying it, people are going to wonder who has done that to him - and why. It makes him sound like a victim of some violent act (or at best, a sex offender who's been "treated" by the criminal justice system) and either way will give people completely wrong ideas about him, when the truth is much simpler.

If a guy kept giving me gifts and asking me out after I had already turned him down I would be creeped out. And did he say this had been going on for a year?