Be warned, I am not known for my conciseness, so this could end up being rather a long post.

I am in my twenties, painfully shy, not out, only in the last year properly admitted to myself and accepted that I’m attracted to guys. For the last couple of months I have been emailing someone I met on a certain gay-oriented website (not this one!). We have spoken about everyday things, flirted, talked a bit dirty, exchanged pics etc. and I really like him. We’re both the same age, with little experience, both shy, both single, have a similar sense of humour, seem to have things in common, and I’m attracted to him physically. One of the very few people I’ve thought to myself “you know what, I wouldn’t mind going out with this person”.

So I summoned all my courage and asked if he would like to meet up for a drink or go to the cinema. (Bear in mind I have never asked anyone out before) He replied saying he would like to meet but he couldn’t make that week, so I gave him a couple of other times when I was free to which he replied and said he was still busy, and also nervous as he’d never been on a date before. I sent back a reply in which I basically said I was just as nervous as him as I’d never been on a date before either, so he shouldn’t worry. A week later I got a one line reply back, pretty much “Very busy here, how are things with you?” not really mentioning the date idea at all, and after a couple more flirty messages exchanged both ways, today he’s asked me to send him another pic of myself, but the possibility of a date seems to have been left behind.

I’m a little unsure of what to do next. I don’t want to turn into some sort of pest or stalker that messages every five minutes asking when he might be free, but I really would like that date with him, and don’t want him to think it was an off the cuff ask, because I was being serious about wanting to get to know him better. It surprises me that I feel like this, because up until a couple of weeks ago, I’d have described myself as being perfectly happy being single and not really looking for dates or anything.

Any suggestions?

Tell him he can take a picture of you himself when you meet up for coffee/drink/meal/whatever.

To be brutally honest, I think you should look for ways to mix with "ordinary" people where you live and, for the moment, forget about trying to meet someone special via the net.

I would also suggest you try to find something going in your area on that interests you - then get involved. That way, by sharing a common interest, you can begin to practice "just being yourself" and gradually build up a circle of friends of both sexes.

In short - if you want to make new friends - you have to take a deep breath, grit your teeth and take those first few steps towards making it happen.

Hope this helps!

I feel for you.

You could either

1) Play it cool and keep chatting with him and hope things develop

2) If you want to get over him, ask him bluntly if he has any intensions of meeting, or where he would like to meet you and don't take any excuses. It could hurt though!

Just ask casually if you're still on for a meeting. If he keeps stalling you know it's time to move on.

I think this is a fairly common problem, unsure whether your continued asking is flogging a dead horse, or whether it's kind of romantic. Sometimes you gotta work and put the effort in to go on a date with someone, and it's worth it in the end! Do what feels right.

Yep, I agree. But don't be too casual.

I feel for you; hope it works out for you. You kind of ache inside, don't you?

I'd keep my options open.
Keep on trying for a date with him, but don't rule anyone else out.

Thank you to everybody that took the time to read the post and reply. I am grateful for all the responses.

And what's happening?

I gave him a gentle reminder but he said he really is too busy at the moment. Something else he said makes me think he is even shyer than me and not that used to receiving compliments and so on, so I am going to not make an issue about it and just stick to an email correspondance with him for the moment. It's a shame, but that's life I suppose.

move on from this and good luck in your quest

I guess he is nervous and needs a lot of reassurance.

I wouldn't rule out the possibility of anything happening with him but on the other hand chances are that nothing will so it seems advisable to keep things open and explore other options as well.

Basically, Yorkshire Guy has it (as usual).