Attracted to Best Friend/Roomate's Ex

Visitor's Question from a unknown year old Male
Well first off background - I have never had a girlfriend, never been on a date, haven't kissed a girl in almost 4 years. I am a shy and awkward person. I get nervous around girls, babble and normally don't say anything. Now my issue is this - I am attracted, seriously, to my best friend's ex Tiffany (Tiffany is not her name, but i am dealing with multiple people, so i just used a name to differentiate). Their relationship didn't end well - He got with her because he broke up with his current girlfriend and two days later got with Tiffany. They dated for 2 months. Early december comes along, as does winter break, my best friend goes home and "loses interest"..he breaks up with Tiffany on christmas eve and gets back with his old girlfriend. I know that Tiffany was upset and still has an issue with my friend. The problem lies in where I think Tiffany is one of the most beautiful girls I have ever seen, she is smart, dedicated and determined, and just has an amazing personality. I on the other hand, don't know what i want to do with my life, don't succeed at most things I try, I am smart but probably won't amount to much, I don't have any money (i get federal aid for school, thus i can only earn x amount of money a year, and that goes towards housing, so i am pretty much poor), and i have no experience with women. I'm not that good looking but I think I could be a good boyfriend. She thinks I am smart and that I amaze her with my intellect, she thinks i am a good guy because i do whatever i can for my friends, one of which is her roommate, and she just thinks I am funny. I just would like to know if a relationship with Tiffany is possible. We aren't exactly matches for each other. Its just, I can see myself with her and don't want to miss out on a chance with her. My friends (girls) say it won't work because of what my best friend/roommate did to her, and that it would be awkward for her. My best friend knows i like her and he doesn't care, he thinks it was a mistake to have hooked up with her but doesn't care. I know that things most-likely won't work out or even happen, its just I just want to know if it could work out. Advice
Never say never!

Stranger things have happened. Although the odds are long, you may discover that the two of you are made for each other.

So, get going and ask her out before someone else does.

Better to ask and find out rather than to never know.

Good luck! George

-- from George
One of Your Friendly Advisors at

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