I have the same sort of problem, I find just getting use to the person is a good start.

Hell just start off with saying Good Morning or something (as long as it IS morning) at least its something, no need to go right into asking them out. Get to know them a little if you work at the same place, maybe bring in Coffee and Donuts one day, thats always a good ice breaker and helps get you acquainted with those you work with.

Its best to be yourself, if you're shy, then hell be shy, but GO FOR IT, nothing happens unless you try

Hope this helped somehow

As someone who is tragically and terminally shy, I certainly share your "how the hell can I do this?" thoughts any time in my life it has come up.

The thing is, you just have to do it, shyness and all ... if this cute guy senses your shyness and it matters to him enough that he'd reject you because of it, then you seriously don't need his attention anyway.

Who knows, if you make a complete and total fool of yourself while trying to get that first date he might even find it insanely endearing.

I wish I knew how to ask people out.
My girlie balls suck.

True story: 20 years ago I liked her, never asked her out. 20 years ago she liked me, never asked me out. We went our separate ways. We reconnected last year, revealed we were quick smitten on one another back in the day, and have been delieriously happy in love (ok ok, it has only been a yearish now but...delirious I say, goddammit). We lost 20 years together because neither had the courage to ask the other out. We don't regret things...but...be smarter...let him know. Be a shame to be decades later to learn what might have been if only a simple question had been asked.

i never thought someone who can look so amazing with their clothes off, and posting those pics on the internet would have a hard time asking someone out. just never hit me. you're gorgeous and the dude would be nuts to say no, you cant lose! just approch him with confidence, dudes dig it.

You just have to do it. If they are into you, then they won't care if you are a little awkward about it.

I'm pretty inept when it comes to these things, but IDGAS got it right. I can't imagine anyone not being interested in you, but if he says no, you're no worse off than you are now, he's missing out on someone really special, and everyone here thinks he's batshit crazy. (Though there's always a chance that you'd plant the idea in his mind and he'd come back to you later and see if you were still interested. Don't hang your hat on that, but it's possible.)
I'd hate to see you stop shooting, but that set is a good way to go out.
Good luck!

I'll miss seeing new set form you.

The best opening line I have is....wait for it.....

Hello!

If you can get past that, and it took a lot for me to get to that point, you have it made....

and

I am saddened that this is your last set. But on the other hand I think it is the best set to go out on. It reminds me of those good books that end just at the right moment. The ones where you'd love for there to be a sequel because it was just that good but you know that it is complete and perfect as is.

Well seems everyone is claiming to be shy in your comments. I have no answer either. Guess I too must be human and care about what all them cuties think of me. The advice I like best from the above comments seems to be the "ask him to go out to a _blank_ with you". In other words the smooth going route. Mind you, I'm an easy going guy, so I'm likely biased.

Best of luck. Loved your sets.

I would start by going down to the arcade and challenging his high score. Your rivalry will lead to mutual respect, and then you can join forces to put down a criminal conspiracy. After that, smooches are entirely appropriate.

Just walk up , talk to them, and simply ask them, I was wondering if you'd like to go out sometime. I had a girl ask me out once, it was really fucking awesome. Best of luck to you, you can do it!!

Just do it. It's fine to be awkward. One moment of courage.

I say "So when are we going to get coffee?" If they remotely don't hate you, they'll be happy to pick a time right then and there.

I say play the awkwardness up. You're supposed to be yourself anyway, right? If he digs it, you're golden, if not, it might not have worked out that great anyway. You're outstanding, and chances are he'd be pumped if you did talk to him. Hell, I know I would be. Talk about random things you saw on the street recently. Find out what he's into and what he does. Talk about music. There's a million things. All you gotta do is take what you love, and instead of telling him about it, ask him what he thinks about those things. Just don't forget to seal the deal when the conversation is going well, and don't let it wind down too long before you ask if he wants to get together. At the very least get his number.

And for the love of God, do NOT stop shooting! I never would have guessed you were turning 30, and I have to say, you're doing a pretty damn good job so far! Maybe start trying things you've never done before in your sets. Some role-playing, perhaps?