Akward Situation...to say the least

[Symptom_of_Society]

So for the past few years, I have liked a classmate of mine. We have gradually become pretty good friends. I am graduating this year, and nows my chance (finally) to start a relationship. However there are several things that have me struggling. First, I am not sure she sees me that way in any way. Because we are such good friends, I worry hurting our friendship by crossing that line. There have been slim instances in our friendship that have indicated to me that she likes me. Also, while not in a relationship and not interested in one with this person, she has a "friend with benefits"...I am not sure how to take this. But, I really like her, and have since my Sophomore year. I don't want to graduate with 3 years of inaction and cowardice on my shoulders. I have never dated. Any advice on what I should do and how I should go about it? Should I let it go?  

[Taeryyn]

I really wish I had something helpful to offer, especially considering how many times I've encountered people who are in the same situation, but I'm afraid I don't.
Every scenario is different, and you're already aware of the options and their potential consequences.
In threads like these, inevitably there are those who will encourage you to take the risk, while others will suggest that it would be more prudent to just maintain your friendship rather than risk it. Either could be right choice, but we have no way of knowing; it works out for some people, and not for others. sweatdrop

You know your friend better than any of us. Do the two of you have any other mutual friends that you trust? If so, it might be a good idea to get their perspective.

An indirect option would be to simply start being flirtatious with her, and then try and gauge her reaction. That said, I see two potential problems with this method. First, she might not take the hint, or may misinterpret it. Second, even if she does respond positively to flirting, she may be open to the idea of being friends with benefits, but nothing more.

Wish I could be of more help. sad  

[Symptom_of_Society]

Taeryyn

I really wish I had something helpful to offer, especially considering how many times I've encountered people who are in the same situation, but I'm afraid I don't.
Every scenario is different, and you're already aware of the options and their potential consequences.
In threads like these, inevitably there are those who will encourage you to take the risk, while others will suggest that it would be more prudent to just maintain your friendship rather than risk it. Either could be right choice, but we have no way of knowing; it works out for some people, and not for others. sweatdrop

You know your friend better than any of us. Do the two of you have any other mutual friends that you trust? If so, it might be a good idea to get their perspective.

An indirect option would be to simply start being flirtatious with her, and then try and gauge her reaction. That said, I see two potential problems with this method. First, she might not take the hint, or may misinterpret it. Second, even if she does respond positively to flirting, she may be open to the idea of being friends with benefits, but nothing more.

Wish I could be of more help. sad

Thank you, I appreciate your insight on this whee it helps more than you'd think  

[AmeliaParadox]

I don't think its awkward.

Waiting for moments and all that crap is something TV and stories makes people do.

in the real world, its better to just get out with it and ask them, that way if they don't feel the same you don't waste time crushing on them.  

[Gummy burrs]

It would help a lot if you knew more about her romantic and sexual preferences - I just don't know how you would, or if you should, try to find out by bringing it up in conversation.

I tend to get really nervous and I trip over my words when I try to start a relationship with someone...so that's why I'm unsure if you want to bring up those topics in conversation while having the intention of getting closer to her.

Do what you feel is best. It's better that you stick to your own pace than to take someone's love advice and try to adjust to the adviser's pace.

Good luck! : )