Younger Guy, Help =)

Here’s my take. Accept it with as much or as little salt as you desire.

My problem is knowing whether he's interested. I sent him a photo, he never commented about it right away(sent it in a private message when he wasn't online), but did comment he didnt think I would find it hard to find someone on the site if I put a photo up.

At first glance (sorry mate, couldn’t resist), that’s not a good sign. Men tend to be more into a woman’s looks than women are into men’s looks – at least with respect to overall attraction. But then again, he is shy and his way of telling you he finds you attractive may be by saying he thinks you’ll be successful finding other men on the site.



I aren't entirely sure that if he was interested he'd let me know how inexperienced he is. And wonder if he see's me more as someone to confide in?

That’s possible. But if he’s as shy as you think he is, it’s really hard to get a read on what his intentions are and what he’s really feeling.



A male friend of mine said no guy would stay up all night talking to someone they wouldn't want to meet.

Your male friend is mostly right, but going from talking online to meeting in person can be a pretty big step, especially for someone who claims to be shy. I’ve spent plenty of time talking to someone online before deciding I was ready to meet them in person. Sometimes it takes a few nights, other times it takes over a year (no joke).



I know he's shy and doesnt know how to act around women (he's told me this) but I aren't sure if that’s the problem here or just that he's not into me.

It can really go in either direction. Initially, I’d say he’s not that into you, but he claims to be shy and I’d give him that benefit of the doubt. Assuming he really is shy, I’d say that more likely than not, he’s into you. But if he’s really that shy, I think you’ll need to take things slowly and carefully. Most of all, you may need to take a very reassuring approach in your interactions with him if you hope to meet in person.
 
If you've heard from him since you sent the photo, then I think you're OK, even if he hasn't commented on it specifically. If you haven't heard from him, then you have your answer. Sorry. Don't bother to pursue.

There are lots of reasons people online won't meet and "shyness" is often a cover up for a person who's nothing like what he's claimed: doesn't look like his photos, isn't 19, is actually married, etc. Unless you're only interested in online chit chat, I wouldn't worry about scaring him off by insisting on meeting. If you do scare him off, it's likely he was never who you thought he was anyway.

Tell him you've had some bad experiences with online relationships that never moved into the real world (if you haven't, don't worry, there are plenty of us who have) and that you prefer to meet sooner rather than later. Suggest coffee or a walk in the park, something in daytime in public, very non-threatening. If he won't do it or says he will but keeps canceling or not showing claiming "shyness", consider him done.

Because I'm that sort of person, I have to point out that you should say "I'm not sure" rather than "I aren't sure." If English isn't your first language, you're doing very well other than that. If English is your first language, "I aren't sure" is making you sound ignorant.
 
This is such an alien situation for me to be in, so I'm feeling pretty stupid at the moment with all this confusion and hesitation!

Don't!

I think you're pretty rational and level headed, so you have little to worry about (except the usual, is this guy a creep and stuff like that, but I think you've reasonably concluded he's not :)).

Best of luck and keep us posted if you can.
 
it is a dating site, not a find your life-mate site...use it as such. I say go for it. What is there to lose? If you don't click in real life...what is lost at this point? A couple of all-nighters and one date. If you are worried...make it a lunch or coffee...or an art museum visit.
 
Instead of going through all this over thinking and second guessing, wouldn't it just be easier to go for it and see what happens?

If you're worried that he hasn't commented on your photo maybe he just doesn't know what to say. He may be conscious about seeming too eager or turning you off by saying you're beautiful assuming you get that a lot on the site. Or maybe he's under the impression that he shouldn't seem too eager in case that puts you off.

Why not just ask him to meet if that's what you want (somewhere public obviously)? All he can do is say no.
 
20 more days to xmas, best of luck ;)

if i'm that guy, i'd take the chance to ask you out, hehe...but i'm not a very shy person, maybe a bit.

1 thing though, did you ever consider stolen identity?
 
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