This was sent to Aunt Babz via email...
Why would it be awkward to hang out with this Jake guy without Emily? Do you feel like you are not being truthful to Emily and are crossing a line? Does Emily like Jake and you know this? That is my first gut instinct because when a girl likes a guy she does what she can to see if the feeling is mutual. And you will not get a good ‘read’ if you idly let things go by.
If Jake isn’t interested in you, well you will know. And even in this day and age of ‘IM’ing… that is just not personal. And you don’t get the quality of feeling and humanity from it. So you will need to talk to him in person.
One thing that I will say is that you cannot compare yourself to Emily. It is just not fair to your well being. You need to establish that you are of worth, and that you can have people in your life without measuring it to someone else. That is about the best advice I can give you. Be yourself and be of worth to yourself. You sound like a nice girl, and you will get to a place where you are happy with who is in your life. So stop comparing yourself, with your friend. Maybe she isn’t all that happy with the guys she attracts, and it isn’t her fault that they are attracted to her. The worst thing you could do is to be jealous over something so uncontrollable, because you will lose a friend and become bitter. You don’t want that.
Of course it isn’t easy seeing all the guys flock to Emily, and I am in no way saying that you should shrink back like a wall flower. Be yourself, but also have a little bit of adventure. Talk to people a little more, and to their faces instead of in an instant message. Gradually you will see the change it brings, and I am sure you will be happy with the outcome.