I'm an incredible wuss

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Just got back from a driving range (yes for golf) with this girl I'm really into. Was all prepared to directly ask her out and I chickened out at the last second.

f**k me.

Well, you already played golf together, why not just call her sometime and ask if she wants to go golfing with you again?

Go for it.

You know, the girl my roommate's with, he's with her just on account that he met her at a club through some mutual friends and invited her out rollerblading. I don't know that he had any further intent but things just fell into place. When you do have that "Lets go out and do something" together by yourselves barrier broken - it almost seems a bit excessive to 'ask some one out' as its almost an unwritten understanding of sorts at that point. If she does want to do more things together with you, you'll see if it starts gliding in a romantic direction - just be sure to meet her half way if she does start displaying signs that she wants to take it there. Otherwise, just enjoy having a close female friend to do things with.

go for it darlin

I'll echo the prevailing sentiment here: go for it. She's already proven she wants to spend time with you, so you really don't have much to lose

There ARE extenuating circumstances... such as the fact shes been a friend of mine for quite a while so spending time with me isn't out of the range of norm. However I did take her out to a nice place for dinner a while ago and another about 2 weeks ago, her wanting to pay the second time.

I just don't know how to get what I want across without being so direct it might as well be written in blood.

Meh, don't let it get you down. I've done the same thing more than once. You just kinda have to jump on into it when you feel it's right and then, "win or lose" it's much better than that god damn regret.

Well, glad I'm a wuss. Bit of intel says she has no interest in me whatsoever.

Doesn't stop me from feeling crushed.