How to Ask a Guy Without Being Obvious?

[Edmundus1581]

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Also. When communicating via writing (i.e. chat, etc.) he often uses a lot of emoticons, and he’s been doing a lot more lately, whereas when we met, he never did it. He uses the one the most often. Is that flirting? He’s kind of a serious guy (though he has a great sense of humor- he just is pretty serious and not given to such things ordinarily).
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You have received some great advise here, even if it doesn’t form a consensus.

This (quoted) really stood out to me. I think you are correct to infer something into the tone of his chats and emails, and the use of emoticons.

A man is cautious about showing his feeling, just as a woman is. Not only out of shyness or fear, but out of respect for the seriousness of everything that’s involved here (marriage, children, etc).

Ten years ago I pursued a lady with email and chats (via a Catholic forum) and when her tone and the emoticons changed was the turning point in our relationship. It didn’t’ work out in the end, but we did have a genuine courtship.

You might want to think about whether you really want a man who’s main emoticon is: . I wouldn’t use it with a lady (much), but then I’m over 50. This is all very complex.

 

[Captain_America]

My two cents:

As a young man, I am intimidated about showing my feelings for a young woman because I don’t want to make things awkward between us if she doesn’t feel the same way. There is someone I like right now, and I’m getting the feeling that she may like me, but I am also terrible at reading people (as far as I know, at least). I’ll say two things.

1. I probably should say something because it’s better to find out than be left wondering and miss an opportunity, and this is true for women as well.
2. If she were to tell me that she likes me, that would be awesome. Even if I didn’t have feelings for her, I’d still be flattered and wouldn’t take it negatively at all.

What’s this with even verbalizing it? Do you date or not?

If you want him to ask you out, then the next time you’re alone with him just start talking about cool new movies you’d like to see, or a game you’d like to go to, etc. Heck, you might even say, “there’s a fabulous new French restaurant in town and I’d love to see its menu.” If he’s halfway sharp, he can take it from there.