Need help making it happen with this girl. Please help!

[nycdude]

Hi everybody, I would really appreciate some advice/help with this situation:

For the past several months I've become quite friendly with a coworker. We're both the same age (24). She's pretty much initiated everything with me from the very beginning since she started working there - the chats at work, the constant daily texting with me when we're off or after work, and the hanging out we've done here and there. We have some minor flirting going on here and there sometimes. I'm really attracted to her and wanna hook up with her, and I think there is a good possibility she may be interested.

Here is the problem: I am not a very experienced seducer and don't know how to go about escalating things with her, and she is (by her own admission) a shy person. I think she might be even less experienced than I am. We both seem to be quite comfortable with each other, but we've never been physical with each other in any way, and I just don't know what would be the best way to go about initiating it. I don't want to just kiss her out of the blue, as that might make her too feel too surprised and uncomfortable. On the other hand, I don't want to be formal and say "would you go out on a date with me" as that is a bit too lame I think.

Next time I'm going to be hanging out with her in the next few days, I want to make my move. But I just don't know how to go about letting her know that I'm interested in taking things with her to a higher level. Any help is appreciated!

[devonbrown]

I am a bit confused. You say she says she is a shy person, but she has been the one initiating everything with you? If she is really shy and she is still initiating things with you, then she probably really likes you and wants things to go further. If she isn't really shy, she may just be saying that because she thinks you need to play the "man role" to make the moves on her. Either way, it appears she is into you like you are into her.
Instead of saying, "Let's go on a date," just ask her if she would like to see a movie and have dinner with you. Dinner and a movie is pretty standard date activity, so she should pick up on that. If she says yes, assume she knows it is a date and proceed accordingly. If she suggests bringing some other friends along, pull back a bit because she is definitely not ready for another step quite yet.

[nycdude]

Thanks for the reply.

The thing is, she and I have already done the whole movie & drinks bit. Several times over. Just me and her, both at my initiative and her own (hers was the first). And I'm sure she'd love to do it again. It's just that now that we've been there before several times, I don't know how exactly I should make the transition to it being an "I'm interested in you" kind of outing than a "lets hang out" thing.

As for her shyness, she has said that she's shy several times when I tried to steer the topic of discussion to a slight sexual nature. That's what's also got me feeling a bit awkward here. I don't want to come on to her in any way that would make her uncomfortable. She's never said anything directly, but from our conversations I have gotten the implication that she's not very romantically/physically experienced, which I guess is the reason for her shyness (or maybe the other way around)