Advice?!

[kingOFcalifornication]

Greetings.

I've been mulling over a situation the past few hours, trying to figure out a reasonable course of action. I think I know what I'm going to do about it, but I'm also curious to see what outside parties might have to say. So, here goes.

A couple of years ago, I started 'talking' to a girl I went to high school with. I'll refer to her as Jane. Well, before we even started dating I began forming a friendship with Jane's best friend. I'll refer to her as Jill. This was a result of Jill offering me advice about pursuing a relationship with Jane. Well, things went fairly well so Jane and I decided to date. Maybe two months in, Jane began to hate Jill because of my friendship with the latter. Jane broke her friendship with Jill. Jill, however, was adamant about remaining friends with me. She had by now begun to consider me her best friend. Now, I understand it wasn't the best idea on my part to be friends with Jill, but that's besides the point. Near the end of my relationship with Jane, I developed a crush on Jill. She tended to flirt with me a lot and I could only assume she liked me at some point. There was a lot of physical contact, etc. between us. Anyways, after I broke up with Jane I still hadn't plucked up the courage to tell Jill. Before long, it was too late and Jill began dating someone. They dated for four or five months and just broke up a few days ago. Of course, I still like her. However, I'm not sure if she still might feel anything towards me at this point. We've been friends and hung out pretty regularly this entire time, minus the last couple of weeks. However, today she made a point to tell me she missed me. That's what sort of resurfaced this question of pursuing a relationship with her. Oh, and she's going off to college 3+ hours away in about a month.

Now, logic would leave me to believe that it's best to let the situation go and not tell her. I value her friendship, we have mutual friends, and I have no interest in making things awkward or having our mutual friends know I have a huge crush on her if she doesn't reciprocate the feelings. Plus, I have absolutely no idea at this point if she might be interested in me. Not the slightest clue.

Anyone care to give me their thought on the situation? I can further elaborate if need be.

[Brandon]

Before I say anything I think that I should point out that Im probably not the best person to get relationship advice from due to the fact that my duo relationships tend to be often but short lived and I continue going back to a love triangle when I find they arent working out.

That said, heres what I think. Jill showed some interest in the past, she said she misses you now, and you guys obviously get along well if you hang out a lot. The question I think you need to ask yourself is "Is being friends enough for me?". 5-10 years down the road will you be content as just friends or will there be that wonder or even regret that there could have been something more?  If being friends is enough then it might be best not to pursue her but if you think its worth the risk then without a doubt ask her out.

[Jude]

How hot is Jill?  We need a picture before we can decide.  Nudes preferably.

(p.s. In all seriousness you should go for it, if things go badly it'll all blow over while you're away at college)

[sartracker]

OK my friend,
For what it is worth, you will live to regret it if you don't let her now that you still have feelings for her. She has obviously expressed that she has feelings for you. Long  distance relationships can work, But there is always the possibility that it won't. It might start of great and slowly drift away. Either way you would never know and spend the rest of your life wondering. Even if you  fell in love with someone else, got married had etc, etc. In the back of your mind it would be there. You have nothing to lose my friend. What ever happens you won't have to look back and wonder what if?
Good Luck and let me know if you think I am right!

[LIAR]

I'm of the opinion you should always go for it. What's a little bit of heartbreak in the long scheme of life if it happens to not work out?

[sartracker]

Well it's unanimous! Go for it!

[kingOFcalifornication]

Lolz. I expected responses such as this.

Thanks everyone.

Rest assured, I'm working up the nerve to bring up the subject with her. I can't find any logical reason not to do so.

[MasterMischief]

What is the worst that could happen and how likely is it to really happen.  Your friends might find out you have a crush one her?  ZOMG!  Noooooo!  Sure, your friends might rib on you some...but if it isn't for this, they'll just find something else.

What are friends for if not to take you down a notch or two occassionally?